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Lenny's Podcast: Product | Career | Growth

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Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
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Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
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Tomer Cohen is the chief product officer at LinkedIn, responsible for setting the company’s product strategy, leading product development, user experience design, business development, content creation, and customer operations. He also hosts the Building One podcast, where he interviews exceptional builders across various disciplines. In our conversation, we discuss:

• How LinkedIn transformed its feed into an engaging content and social platform

• Tomer’s famous “We might be wrong, but we are not confused” mantra

• The importance of conviction and passion in product leadership

• LinkedIn’s approach to experimenting with and implementing AI features

• Lessons from Tomer’s rapid career progression at LinkedIn

• Strategies for embracing AI in product development

Brought to you by:

Gamma—A new way to present, powered by AI

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Merge—A single API to add hundreds of integrations into your app

Find the transcript at: https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

Where to find Tomer Cohen:

• LinkedIn: https://www.linkedin.com/in/tomercohen/

• Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Tomer Cohen and his role at LinkedIn

(02:28) The mantra “We might be wrong, but we are not confused”

(06:45) Clarity of thought and focus

(13:03) Setting ambitious goals and overdelivering

(16:18) Transforming LinkedIn’s feed: strategy and execution

(22:03) Running experiments at scale

(26:24) Goal setting and identifying opportunities 

(30:58) AI’s role in LinkedIn’s evolution

(35:38) The AI-first mindset at LinkedIn

(35:38) Developing an AI-first mindset

(44:49) Letting go of your roadmaps and allowing room for exploration

(49:12) Career growth and personal insights

(55:01) Takeaways

(56:39) Lightning round and final thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Tomer Cohen is the chief product officer at LinkedIn, responsible for setting the company’s product strategy, leading product development, user experience design, business development, content creation, and customer operations. He also hosts the Building One podcast, where he interviews exceptional builders across various disciplines. In our conversation, we discuss:

• How LinkedIn transformed its feed into an engaging content and social platform

• Tomer’s famous “We might be wrong, but we are not confused” mantra

• The importance of conviction and passion in product leadership

• LinkedIn’s approach to experimenting with and implementing AI features

• Lessons from Tomer’s rapid career progression at LinkedIn

• Strategies for embracing AI in product development

Brought to you by:

Gamma—A new way to present, powered by AI

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Merge—A single API to add hundreds of integrations into your app

Find the transcript at: https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

Where to find Tomer Cohen:

• LinkedIn: https://www.linkedin.com/in/tomercohen/

• Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Tomer Cohen and his role at LinkedIn

(02:28) The mantra “We might be wrong, but we are not confused”

(06:45) Clarity of thought and focus

(13:03) Setting ambitious goals and overdelivering

(16:18) Transforming LinkedIn’s feed: strategy and execution

(22:03) Running experiments at scale

(26:24) Goal setting and identifying opportunities 

(30:58) AI’s role in LinkedIn’s evolution

(35:38) The AI-first mindset at LinkedIn

(35:38) Developing an AI-first mindset

(44:49) Letting go of your roadmaps and allowing room for exploration

(49:12) Career growth and personal insights

(55:01) Takeaways

(56:39) Lightning round and final thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sean Ellis is one of the earliest and most influential thinkers and operators in growth. He coined the term “growth hacking,” invented the ICE prioritization framework, was one of the earliest people to use freemium as a growth lever, and, most famously, developed the Sean Ellis Test for product-market fit (which a large percentage of founders use today to track if they’ve found PMF). Over the course of his career, Sean was head of growth at Dropbox and Eventbrite; helped companies like Microsoft and Nubank refine their growth strategy; was on the founding team of LogMeIn, which sold for over $4 billion; and is the author of one of the most popular growth books of all time, Hacking Growth, which has sold over 750,000 copies. In our conversation, he shares:

• The proper use of the Sean Ellis Test for measuring product-market fit

• How to increase your activation and retention rates

• How to select the right North Star metric for your business

• Case studies from his work growing Dropbox and other products

• How growth strategy has changed over the past decade

• How AI is impacting growth efforts

• Much more

Brought to you by:

Gamma—A new way to present, powered by AI

CommandBar—AI-powered user assistance for modern products and impatient users

Merge—A single API to add hundreds of integrations into your app

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis

Where to find Sean Ellis:

• X: https://x.com/seanellis

• LinkedIn: https://www.linkedin.com/in/seanellis/

• Website: https://www.seanellis.me/

• Substack: https://substack.com/@seanellis

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Sean’s background

(02:18) The Sean Ellis test explained

(06:28) The 40% rule

(08:06) Case study: improving product-market fit

(12:34) Understanding and leveraging customer feedback

(16:50) Challenges and nuances of product-market fit

(22:22) When to use the Sean Ellis Test

(23:46) When not to use the Sean Ellis Test and other caveats

(27:13) Defining your own threshold and how the Sean Ellis Test came about

(36:13) Tools for implementing the survey 

(37:30) Transitioning from surveys to retention cohorts

(39:13) Nubank’s approach

(40:18) Case study: Superhuman’s strategy for increasing product-market fit

(45:18) Coining the term “growth hacking”

(48:24) How to approach growth

(57:25) Improving activation and onboarding

(01:05:17) Identifying effective growth channels

(01:10:28) The power of customer conversations

(01:12:43) Developing the Dropbox referral program

(01:14:47) The importance of word of mouth

(01:15:23) Freemium models and engagement

(01:19:21) Picking a North Star metric

(01:24:30) The evolution of growth strategies

(01:27:12) The ICE and RICE frameworks

(01:30:11) AI’s role in growth and experimentation

(01:32:52) Final thoughts and lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Sean Ellis is one of the earliest and most influential thinkers and operators in growth. He coined the term “growth hacking,” invented the ICE prioritization framework, was one of the earliest people to use freemium as a growth lever, and, most famously, developed the Sean Ellis Test for product-market fit (which a large percentage of founders use today to track if they’ve found PMF). Over the course of his career, Sean was head of growth at Dropbox and Eventbrite; helped companies like Microsoft and Nubank refine their growth strategy; was on the founding team of LogMeIn, which sold for over $4 billion; and is the author of one of the most popular growth books of all time, Hacking Growth, which has sold over 750,000 copies. In our conversation, he shares:

• The proper use of the Sean Ellis Test for measuring product-market fit

• How to increase your activation and retention rates

• How to select the right North Star metric for your business

• Case studies from his work growing Dropbox and other products

• How growth strategy has changed over the past decade

• How AI is impacting growth efforts

• Much more

Brought to you by:

Gamma—A new way to present, powered by AI

CommandBar—AI-powered user assistance for modern products and impatient users

Merge—A single API to add hundreds of integrations into your app

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis

Where to find Sean Ellis:

• X: https://x.com/seanellis

• LinkedIn: https://www.linkedin.com/in/seanellis/

• Website: https://www.seanellis.me/

• Substack: https://substack.com/@seanellis

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Sean’s background

(02:18) The Sean Ellis test explained

(06:28) The 40% rule

(08:06) Case study: improving product-market fit

(12:34) Understanding and leveraging customer feedback

(16:50) Challenges and nuances of product-market fit

(22:22) When to use the Sean Ellis Test

(23:46) When not to use the Sean Ellis Test and other caveats

(27:13) Defining your own threshold and how the Sean Ellis Test came about

(36:13) Tools for implementing the survey 

(37:30) Transitioning from surveys to retention cohorts

(39:13) Nubank’s approach

(40:18) Case study: Superhuman’s strategy for increasing product-market fit

(45:18) Coining the term “growth hacking”

(48:24) How to approach growth

(57:25) Improving activation and onboarding

(01:05:17) Identifying effective growth channels

(01:10:28) The power of customer conversations

(01:12:43) Developing the Dropbox referral program

(01:14:47) The importance of word of mouth

(01:15:23) Freemium models and engagement

(01:19:21) Picking a North Star metric

(01:24:30) The evolution of growth strategies

(01:27:12) The ICE and RICE frameworks

(01:30:11) AI’s role in growth and experimentation

(01:32:52) Final thoughts and lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Vlad Loktev spent 10 years at Airbnb, where he started as an IC PM and quickly advanced to lead the core Airbnb marketplace business and then GM the entire homes business, managing over 1,000 people and reporting directly to CEO Brian Chesky. He recently left Airbnb and joined Index Ventures as their newest partner. Vlad was my manager at Airbnb for many years, and is the person I credit most for teaching me how to be a great product manager. Prior to Airbnb, Vlad spent a year at Zynga, where he helped grow Words with Friends to over 14 million daily active users. In our conversation, Vlad shares:

• Insight into Brian Chesky’s leadership style

• Why success as a PM is all about impact, impact, impact

• Why chaos can be good

• Why as a leader it’s OK to let some fires burn

• Why you should learn to “poke the bear”

• Balancing product release speed with quality

• Lessons on prioritization, decision-making, and organizational design

• Advice for founders on building company culture

• Much more

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Vanta—Automate compliance. Simplify security

Eppo—Run reliable, impactful experiments

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

Where to find Vlad Loktev:

• X: https://x.com/vladimirloktev

• LinkedIn: https://www.linkedin.com/in/vladimirloktev/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Vlad’s background

(02:54) Reflecting on transformative years at Airbnb

(04:28) Skills and mindsets for success

(11:03) Impact-driven mindset

(13:16) Saying no and inquiry before advocacy 

(17:54) “Poking the bear”

(22:46) Psychological tools for leadership

(30:08) Building and scaling teams

(36:12) Letting fires burn

(47:34) Embracing chaos

(54:40) The unsell email strategy

(01:02:01) Finding your place in an organization

(01:05:38) The importance of company culture

(01:13:16) Airbnb’s unique approach to product management

(01:26:41) Failure corner

(01:31:32) Lightning round and final thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Vlad Loktev spent 10 years at Airbnb, where he started as an IC PM and quickly advanced to lead the core Airbnb marketplace business and then GM the entire homes business, managing over 1,000 people and reporting directly to CEO Brian Chesky. He recently left Airbnb and joined Index Ventures as their newest partner. Vlad was my manager at Airbnb for many years, and is the person I credit most for teaching me how to be a great product manager. Prior to Airbnb, Vlad spent a year at Zynga, where he helped grow Words with Friends to over 14 million daily active users. In our conversation, Vlad shares:

• Insight into Brian Chesky’s leadership style

• Why success as a PM is all about impact, impact, impact

• Why chaos can be good

• Why as a leader it’s OK to let some fires burn

• Why you should learn to “poke the bear”

• Balancing product release speed with quality

• Lessons on prioritization, decision-making, and organizational design

• Advice for founders on building company culture

• Much more

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Vanta—Automate compliance. Simplify security

Eppo—Run reliable, impactful experiments

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

Where to find Vlad Loktev:

• X: https://x.com/vladimirloktev

• LinkedIn: https://www.linkedin.com/in/vladimirloktev/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Vlad’s background

(02:54) Reflecting on transformative years at Airbnb

(04:28) Skills and mindsets for success

(11:03) Impact-driven mindset

(13:16) Saying no and inquiry before advocacy 

(17:54) “Poking the bear”

(22:46) Psychological tools for leadership

(30:08) Building and scaling teams

(36:12) Letting fires burn

(47:34) Embracing chaos

(54:40) The unsell email strategy

(01:02:01) Finding your place in an organization

(01:05:38) The importance of company culture

(01:13:16) Airbnb’s unique approach to product management

(01:26:41) Failure corner

(01:31:32) Lightning round and final thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
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Nikita Bier is one of the most in-demand consumer, social, and growth experts in the world. He’s the co-founder of TBH (sold to Meta for more than $30 million) and Gas (sold to Discord for millions more) and has helped more consumer apps that have hit #1 in the app stores than any other person I’ve come across. He currently spends his time advising founders on growth, product, and design and is an investor and advisor to some of the best consumer tech companies, including Flo, Locket, Eight Sleep, Citizen, BeReal, Captions, and more. In our conversation, we discuss:

• The inside story of how TBH and Gas achieved explosive growth

• Strategies for building viral consumer apps

• Why teens are such a great audience

• Fighting the human trafficking hoax at Gas

• The challenge of creating durable social products

• His experience working as a PM at Facebook

• Advice for founders on building consumer apps

• Much more

Brought to you by:

Webflow—The web experience platform

Vanta—Automate compliance. Simplify security

Explo—Embed customer-facing analytics in your product

Book Nikita for 1:1 consultation/mentoring: https://intro.co/NikitaBier

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier

Where to find Nikita Bier:

• X: https://x.com/nikitabier 

• Threads: https://www.threads.net/@nikitabier

• Website: https://intro.co/NikitaBier

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Nikita’s background 

(06:08) Nikita’s early ventures: Politify and Outline

(08:42) Transition to consumer apps

(13:45) The birth of TBH

(16:43) Building for teens vs. adults

(20:00) TBH’s viral success

(32:18) Leveraging live chat

(34:08) Lasting lessons from TBH

(37:00) Selling TBH to Facebook

(42:19) Big-tech product management

(48:46) Nikita on why “product management is not real”

(51:49) The Tim Cook painting story

(53:53) Leaving Facebook and starting a new venture

(58:02) Rebuilding TBH and overcoming challenges

(59:46) Addressing criticism

(01:04:24) The human trafficking hoax

(01:09:51) Selling to Discord and lessons learned

(01:11:36) Lasting lessons from Gas

(01:13:14) Building durable consumer apps

(01:22:35) The VC route

(01:23:27) Contact permissions in iOS 18

(01:26:53) The success of Dupe

(01:31:53) Advice for startup founders

(01:34:14) Work with Nikita

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Nikita Bier is one of the most in-demand consumer, social, and growth experts in the world. He’s the co-founder of TBH (sold to Meta for more than $30 million) and Gas (sold to Discord for millions more) and has helped more consumer apps that have hit #1 in the app stores than any other person I’ve come across. He currently spends his time advising founders on growth, product, and design and is an investor and advisor to some of the best consumer tech companies, including Flo, Locket, Eight Sleep, Citizen, BeReal, Captions, and more. In our conversation, we discuss:

• The inside story of how TBH and Gas achieved explosive growth

• Strategies for building viral consumer apps

• Why teens are such a great audience

• Fighting the human trafficking hoax at Gas

• The challenge of creating durable social products

• His experience working as a PM at Facebook

• Advice for founders on building consumer apps

• Much more

Brought to you by:

Webflow—The web experience platform

Vanta—Automate compliance. Simplify security

Explo—Embed customer-facing analytics in your product

Book Nikita for 1:1 consultation/mentoring: https://intro.co/NikitaBier

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier

Where to find Nikita Bier:

• X: https://x.com/nikitabier 

• Threads: https://www.threads.net/@nikitabier

• Website: https://intro.co/NikitaBier

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Nikita’s background 

(06:08) Nikita’s early ventures: Politify and Outline

(08:42) Transition to consumer apps

(13:45) The birth of TBH

(16:43) Building for teens vs. adults

(20:00) TBH’s viral success

(32:18) Leveraging live chat

(34:08) Lasting lessons from TBH

(37:00) Selling TBH to Facebook

(42:19) Big-tech product management

(48:46) Nikita on why “product management is not real”

(51:49) The Tim Cook painting story

(53:53) Leaving Facebook and starting a new venture

(58:02) Rebuilding TBH and overcoming challenges

(59:46) Addressing criticism

(01:04:24) The human trafficking hoax

(01:09:51) Selling to Discord and lessons learned

(01:11:36) Lasting lessons from Gas

(01:13:14) Building durable consumer apps

(01:22:35) The VC route

(01:23:27) Contact permissions in iOS 18

(01:26:53) The success of Dupe

(01:31:53) Advice for startup founders

(01:34:14) Work with Nikita

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Deb Liu is the CEO of Ancestry and former longtime VP of Product at Facebook. At Facebook, Deb led the creation of Facebook Marketplace, developed the first mobile ad product for apps, built the company’s games business, and launched Facebook Pay. She’s also held leadership roles at PayPal and eBay, serves on the board of Intuit, and is the author of Take Back Your Power. In our conversation, we discuss:

• Why you should PM your career like you PM your product

• Strategies for incubating new products within large companies

• Creating a successful 30-60-90-day plan when starting a new job

• The pitfalls of perfectionism

• The challenges introverts face in the workplace and how to overcome them

• The value of resilience and turning failures into stepping stones

• How to leverage coaching in your career development

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Webflow—The web experience platform

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/succeeding-as-an-introvert-deb-liu

Where to find Deb Liu:

• Threads: https://www.threads.net/@debliu

• LinkedIn: https://www.linkedin.com/in/deborahliu

• Substack: https://debliu.substack.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Deb Liu

(02:18) Deb’s career journey and key advice

(09:45) Navigating new roles and challenges

(11:27) Overcoming adversity and failure

(15:07) Building billion-dollar businesses at Facebook

(19:33) Strategies for zero-to-one innovation

(23:40) PM your career like a product

(33:53) Challenges and strategies for introverts in business

(39:19) Reframing self-promotion

(42:25) The power of accountability

(46:15) Growth: a game of inches

(50:52) The 30-60-90-day plan

(56:52) Contrarian corner: career and marriage

(58:57) Final nuggets of wisdom

(01:03:09) How to find a coach

(01:04:47) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Deb Liu is the CEO of Ancestry and former longtime VP of Product at Facebook. At Facebook, Deb led the creation of Facebook Marketplace, developed the first mobile ad product for apps, built the company’s games business, and launched Facebook Pay. She’s also held leadership roles at PayPal and eBay, serves on the board of Intuit, and is the author of Take Back Your Power. In our conversation, we discuss:

• Why you should PM your career like you PM your product

• Strategies for incubating new products within large companies

• Creating a successful 30-60-90-day plan when starting a new job

• The pitfalls of perfectionism

• The challenges introverts face in the workplace and how to overcome them

• The value of resilience and turning failures into stepping stones

• How to leverage coaching in your career development

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Webflow—The web experience platform

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/succeeding-as-an-introvert-deb-liu

Where to find Deb Liu:

• Threads: https://www.threads.net/@debliu

• LinkedIn: https://www.linkedin.com/in/deborahliu

• Substack: https://debliu.substack.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Deb Liu

(02:18) Deb’s career journey and key advice

(09:45) Navigating new roles and challenges

(11:27) Overcoming adversity and failure

(15:07) Building billion-dollar businesses at Facebook

(19:33) Strategies for zero-to-one innovation

(23:40) PM your career like a product

(33:53) Challenges and strategies for introverts in business

(39:19) Reframing self-promotion

(42:25) The power of accountability

(46:15) Growth: a game of inches

(50:52) The 30-60-90-day plan

(56:52) Contrarian corner: career and marriage

(58:57) Final nuggets of wisdom

(01:03:09) How to find a coach

(01:04:47) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kevin Yien leads product for merchant experiences at Stripe. Before that, he meandered his way from being a technical designer to a product manager, built the restaurants business and ecosystem team at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and teaches for fun. In our conversation, we discuss:

• Why aspiring PMs should start in engineering, design, or sales

• The importance of writing skills, and how to become a better writer

• How to automate user research

• Kevin’s “unsell email” technique for hiring

• The value of keeping a decision log

• Insights on AI and its impact on future generations

• Lessons from failure

Brought to you by:

BuildBetter—AI for product teams

OneSchema—Import CSV data 10x faster

Eppo—Run reliable, impactful experiments

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien

Where to find Kevin Yien:

• X: https://x.com/kevinyien

• LinkedIn: https://www.linkedin.com/in/kevinyien/

• Website: https://kevinyien.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kevin’s background 

(02:00) The story behind Kevin’s profile picture

(08:41) The role of a product manager

(10:48) Getting started in product management

(12:47) The importance of writing skills

(15:06) Becoming a better writer

(19:10) The PM’s role with engineering and design

(28:41) Drawing the perimeter for your team

(31:37) Feedback tips

(35:13) Decision logs and product sense

(45:36) Unorthodox hiring strategies

(47:01) The unsell email strategy

(54:01) Automating user research

(01:02:27) AI in everyday life

(01:06:05) Lessons from failure

(01:14:34) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Kevin Yien leads product for merchant experiences at Stripe. Before that, he meandered his way from being a technical designer to a product manager, built the restaurants business and ecosystem team at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and teaches for fun. In our conversation, we discuss:

• Why aspiring PMs should start in engineering, design, or sales

• The importance of writing skills, and how to become a better writer

• How to automate user research

• Kevin’s “unsell email” technique for hiring

• The value of keeping a decision log

• Insights on AI and its impact on future generations

• Lessons from failure

Brought to you by:

BuildBetter—AI for product teams

OneSchema—Import CSV data 10x faster

Eppo—Run reliable, impactful experiments

Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien

Where to find Kevin Yien:

• X: https://x.com/kevinyien

• LinkedIn: https://www.linkedin.com/in/kevinyien/

• Website: https://kevinyien.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kevin’s background 

(02:00) The story behind Kevin’s profile picture

(08:41) The role of a product manager

(10:48) Getting started in product management

(12:47) The importance of writing skills

(15:06) Becoming a better writer

(19:10) The PM’s role with engineering and design

(28:41) Drawing the perimeter for your team

(31:37) Feedback tips

(35:13) Decision logs and product sense

(45:36) Unorthodox hiring strategies

(47:01) The unsell email strategy

(54:01) Automating user research

(01:02:27) AI in everyday life

(01:06:05) Lessons from failure

(01:14:34) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Evan LaPointe is the founder of CORE Sciences, which teaches companies and individuals how our brains work and how that translates to improved collaboration, better products, faster decision-making, and more growth. Previously, Evan was the co-founder of Satellite, the fourth-largest analytics product on the internet today (it mostly runs behind the scenes, and pretty much everyone listening will have used it today without knowing it), which was acquired by Adobe, where he later ran product strategy, innovation, and long-range thinking for Adobe’s digital experiences business. In our conversation, we discuss:

• The three different systems of the brain

• How knowing this can help you become more influential

• How understanding different brain states will help you increase productivity and creativity

• How to improve your vision and strategy skills

• How to design a work environment that fosters innovation

• How to build better relationships at work

• Much more

Use discount code “LENNY” for $5 off the CORE Sciences personality profile: https://www.core-sciences.com/new-core-identity

Brought to you by:

Webflow—The web experience platform

Explo—Embed customer-facing analytics in your product

Eppo—Run reliable, impactful experiments

Find the transcript and references at: https://www.lennysnewsletter.com/p/understanding-your-brain-evan-lapointe

Where to find Evan LaPointe:

• X: https://x.com/evanlapointe

• LinkedIn: https://www.linkedin.com/in/evanlapointe/

• Website: https://www.core-sciences.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Evan’s background

(02:37) Understanding the brain’s complex systems

(07:17) The three core brain systems: safety, reward, and purpose

(11:03) Applying brain science to team dynamics

(14:27) The role of personality in team performance

(17:27) Creating effective work environments

(23:16) The science of meetings and decision-making

(29:35) Enhancing strategy and vision

(54:46) Understanding personality traits in strategy and vision

(58:58) Tactical tips for increasing openness

(01:05:46) Building influence and effective relationships

(01:21:17) The importance of trust and appeal in relationships

(01:36:47) Creating a positive organizational habitat

(01:50:35) Enhancing focus and productivity

(02:00:58) Practical tips for deep work and gamma time

(02:07:11) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Evan LaPointe is the founder of CORE Sciences, which teaches companies and individuals how our brains work and how that translates to improved collaboration, better products, faster decision-making, and more growth. Previously, Evan was the co-founder of Satellite, the fourth-largest analytics product on the internet today (it mostly runs behind the scenes, and pretty much everyone listening will have used it today without knowing it), which was acquired by Adobe, where he later ran product strategy, innovation, and long-range thinking for Adobe’s digital experiences business. In our conversation, we discuss:

• The three different systems of the brain

• How knowing this can help you become more influential

• How understanding different brain states will help you increase productivity and creativity

• How to improve your vision and strategy skills

• How to design a work environment that fosters innovation

• How to build better relationships at work

• Much more

Use discount code “LENNY” for $5 off the CORE Sciences personality profile: https://www.core-sciences.com/new-core-identity

Brought to you by:

Webflow—The web experience platform

Explo—Embed customer-facing analytics in your product

Eppo—Run reliable, impactful experiments

Find the transcript and references at: https://www.lennysnewsletter.com/p/understanding-your-brain-evan-lapointe

Where to find Evan LaPointe:

• X: https://x.com/evanlapointe

• LinkedIn: https://www.linkedin.com/in/evanlapointe/

• Website: https://www.core-sciences.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Evan’s background

(02:37) Understanding the brain’s complex systems

(07:17) The three core brain systems: safety, reward, and purpose

(11:03) Applying brain science to team dynamics

(14:27) The role of personality in team performance

(17:27) Creating effective work environments

(23:16) The science of meetings and decision-making

(29:35) Enhancing strategy and vision

(54:46) Understanding personality traits in strategy and vision

(58:58) Tactical tips for increasing openness

(01:05:46) Building influence and effective relationships

(01:21:17) The importance of trust and appeal in relationships

(01:36:47) Creating a positive organizational habitat

(01:50:35) Enhancing focus and productivity

(02:00:58) Practical tips for deep work and gamma time

(02:07:11) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Joe Hudson is one of the most sought-after executive coaches in Silicon Valley. He is the founder of Art of Accomplishment, a transformational coaching program that has helped tens of thousands of people, including many tech executives and founders from companies like Apple, OpenAI, and Google. His unique method of transformation comes from over 25 years of exploring neurological, psychological, and spiritual traditions, tested against real-world challenges. In our conversation, Joe shares:

• Why the critical voice in your head is always wrong, and how to change your relationship with that voice

• Why authenticity trumps self-improvement

• The importance of embracing all of your emotions

• How to create more enjoyable and effective meetings

• The power of gratitude in transforming your life

• Practical experiments for personal growth

• Much more

Apply for Joe’s Connection Course:

Thousands of students have taken Joe’s most popular experience, the Connection Course. Unlike most online courses, there is no reading, lectures, or written homework. It is a three-week experiential deep dive where you will apply your learnings to real-life problems—how to make your team more productive, communicate more effectively, and resolve conflicts with ease. Apply here and use the code LENNY for $300 off your enrollment: view.life/lenny.

Brought to you by:

BuildBetter—AI for product teams

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Coda—The all-in-one collaborative workspace

Find the transcript and references at: https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

Where to find Joe Hudson:

• X: https://x.com/FU_joehudson

• LinkedIn: https://www.linkedin.com/in/joe-hudson/

• Website: https://www.artofaccomplishment.com/

• Podcast: https://www.artofaccomplishment.com/podcast

• Linktree: https://linktr.ee/theartofaccomplishment

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Joe’s background

(02:31) The critical voice in your head

(06:39) Changing your relationship with the critical voice

(13:19) Understanding and embracing emotions

(19:52) The importance of emotional fluidity

(24:40) Questioning assumptions and self-perception

(30:25) The consequences of avoiding emotions

(36:57) Experimenting with self-improvement

(39:42) Understanding efficiency and enjoyment

(43:17) The power of enjoyment in daily tasks

(45:03) Innate enjoyment vs. learned enjoyment

(46:31) Authenticity vs. self-improvement

(50:01) Embracing emotional experiences

(55:49) How understanding your emotions helps you make better decisions

(01:02:53) Creating effective teams and meetings

(01:10:40) Gratitude practice for personal growth

(01:15:36) Conclusion and final thoughts

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Joe Hudson is one of the most sought-after executive coaches in Silicon Valley. He is the founder of Art of Accomplishment, a transformational coaching program that has helped tens of thousands of people, including many tech executives and founders from companies like Apple, OpenAI, and Google. His unique method of transformation comes from over 25 years of exploring neurological, psychological, and spiritual traditions, tested against real-world challenges. In our conversation, Joe shares:

• Why the critical voice in your head is always wrong, and how to change your relationship with that voice

• Why authenticity trumps self-improvement

• The importance of embracing all of your emotions

• How to create more enjoyable and effective meetings

• The power of gratitude in transforming your life

• Practical experiments for personal growth

• Much more

Apply for Joe’s Connection Course:

Thousands of students have taken Joe’s most popular experience, the Connection Course. Unlike most online courses, there is no reading, lectures, or written homework. It is a three-week experiential deep dive where you will apply your learnings to real-life problems—how to make your team more productive, communicate more effectively, and resolve conflicts with ease. Apply here and use the code LENNY for $300 off your enrollment: view.life/lenny.

Brought to you by:

BuildBetter—AI for product teams

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Coda—The all-in-one collaborative workspace

Find the transcript and references at: https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

Where to find Joe Hudson:

• X: https://x.com/FU_joehudson

• LinkedIn: https://www.linkedin.com/in/joe-hudson/

• Website: https://www.artofaccomplishment.com/

• Podcast: https://www.artofaccomplishment.com/podcast

• Linktree: https://linktr.ee/theartofaccomplishment

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Joe’s background

(02:31) The critical voice in your head

(06:39) Changing your relationship with the critical voice

(13:19) Understanding and embracing emotions

(19:52) The importance of emotional fluidity

(24:40) Questioning assumptions and self-perception

(30:25) The consequences of avoiding emotions

(36:57) Experimenting with self-improvement

(39:42) Understanding efficiency and enjoyment

(43:17) The power of enjoyment in daily tasks

(45:03) Innate enjoyment vs. learned enjoyment

(46:31) Authenticity vs. self-improvement

(50:01) Embracing emotional experiences

(55:49) How understanding your emotions helps you make better decisions

(01:02:53) Creating effective teams and meetings

(01:10:40) Gratitude practice for personal growth

(01:15:36) Conclusion and final thoughts

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into:

• How to enable product and ops to work well together

• How to run great product reviews

• How to make good decisions with limited data

• How he uses the jobs-to-be-done framework at Opendoor

• How to stay calm under pressure as a leader

• Wild stories from his time at Uber

• Challenges faced at Opendoor during the pandemic

• Much more

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Explo—Embed customer-facing analytics in your product

Attio—The powerful, flexible CRM for fast-growing startups

Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin

Where to find Brian Tolkin:

• X: https://x.com/briantolkin

• LinkedIn: https://www.linkedin.com/in/briantolkin/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Brian’s background

(02:14) Career beginnings at Uber

(02:49) Transitioning from product operations to product management

(06:47) Product and operations synergy

(10:00) Surge pricing at Uber

(12:18) Scaling challenges, and stories

(15:47) Opendoor and Covid adaptations

(25:38) Product reviews and Jobs to Be Done

(40:30) The challenges of A/B testing

(42:23) Increasing conviction in solutions

(44:33) Leveraging intuition in product decisions

(47:07) Partnering with Zillow

(52:55) Staying calm under pressure

(56:25) Finding the “kernel of truth” in product management

(01:00:21) Failure corner: Early days of Uber Pool

(01:06:11) Lightning round and final thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into:

• How to enable product and ops to work well together

• How to run great product reviews

• How to make good decisions with limited data

• How he uses the jobs-to-be-done framework at Opendoor

• How to stay calm under pressure as a leader

• Wild stories from his time at Uber

• Challenges faced at Opendoor during the pandemic

• Much more

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Explo—Embed customer-facing analytics in your product

Attio—The powerful, flexible CRM for fast-growing startups

Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin

Where to find Brian Tolkin:

• X: https://x.com/briantolkin

• LinkedIn: https://www.linkedin.com/in/briantolkin/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Brian’s background

(02:14) Career beginnings at Uber

(02:49) Transitioning from product operations to product management

(06:47) Product and operations synergy

(10:00) Surge pricing at Uber

(12:18) Scaling challenges, and stories

(15:47) Opendoor and Covid adaptations

(25:38) Product reviews and Jobs to Be Done

(40:30) The challenges of A/B testing

(42:23) Increasing conviction in solutions

(44:33) Leveraging intuition in product decisions

(47:07) Partnering with Zillow

(52:55) Staying calm under pressure

(56:25) Finding the “kernel of truth” in product management

(01:00:21) Failure corner: Early days of Uber Pool

(01:06:11) Lightning round and final thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Timothy Davis has led performance marketing for all of Shopify for the past 2.5 years, and as a consultant has helped companies like Pinterest, LinkedIn, Redfin, and Eventbrite kickstart and scale their performance marketing teams. In every one of those cases, he got them so performant at paid growth that they significantly scale spend and investment in these channels. In our conversation, we cover:

• When and how to start investing in performance marketing

• Common mistakes companies make with paid ads

• How to build and structure a performance marketing team

• How to get your creatives performing better

• Strategies for optimizing workflows and team efficiency

• How AI will change performance marketing

• Much more

Brought to you by:

BuildBetter—AI for product teams

OneSchema—Import CSV data 10x faster

Eppo—Run reliable, impactful experiments

Find the transcript and references at: https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis

Where to find Timothy Davis:

• LinkedIn: https://www.linkedin.com/in/timothypatrickdavis/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Timothy’s background 

(02:31) Understanding performance marketing 

(06:31) The importance of paid search 

(08:39) Identifying growth potential 

(09:54) Case studies: Hairstory and Ipsy 

(12:22) Experimenting with new platforms 

(18:57) Choosing the right platforms 

(20:23) LinkedIn for B2B marketing 

(27:56) When to start investing in paid growth 

(33:33) Common mistakes in performance marketing 

(37:41) Working with agencies and consultants 

(40:36) Hiring for performance marketing 

(47:33) Metrics that matter 

(54:43) Competitor analysis and CPC insights 

(56:15) Custom reports and data visualization

(56:38) Understanding impression and click share 

(59:10) True competition metrics 

(01:02:14) Attribution and incrementality 

(01:08:52) Building a performance marketing team 

(01:10:53) Creative and ad copy collaboration 

(01:15:48) Managing workload and hiring strategy 

(01:20:52) Training and onboarding new hires 

(01:24:41) Impact of ATT on performance marketing 

(01:25:56) The power of creative in ads 

(01:29:47) Using AI in performance marketing 

(01:37:16) Lightning round 

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Timothy Davis has led performance marketing for all of Shopify for the past 2.5 years, and as a consultant has helped companies like Pinterest, LinkedIn, Redfin, and Eventbrite kickstart and scale their performance marketing teams. In every one of those cases, he got them so performant at paid growth that they significantly scale spend and investment in these channels. In our conversation, we cover:

• When and how to start investing in performance marketing

• Common mistakes companies make with paid ads

• How to build and structure a performance marketing team

• How to get your creatives performing better

• Strategies for optimizing workflows and team efficiency

• How AI will change performance marketing

• Much more

Brought to you by:

BuildBetter—AI for product teams

OneSchema—Import CSV data 10x faster

Eppo—Run reliable, impactful experiments

Find the transcript and references at: https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis

Where to find Timothy Davis:

• LinkedIn: https://www.linkedin.com/in/timothypatrickdavis/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Timothy’s background 

(02:31) Understanding performance marketing 

(06:31) The importance of paid search 

(08:39) Identifying growth potential 

(09:54) Case studies: Hairstory and Ipsy 

(12:22) Experimenting with new platforms 

(18:57) Choosing the right platforms 

(20:23) LinkedIn for B2B marketing 

(27:56) When to start investing in paid growth 

(33:33) Common mistakes in performance marketing 

(37:41) Working with agencies and consultants 

(40:36) Hiring for performance marketing 

(47:33) Metrics that matter 

(54:43) Competitor analysis and CPC insights 

(56:15) Custom reports and data visualization

(56:38) Understanding impression and click share 

(59:10) True competition metrics 

(01:02:14) Attribution and incrementality 

(01:08:52) Building a performance marketing team 

(01:10:53) Creative and ad copy collaboration 

(01:15:48) Managing workload and hiring strategy 

(01:20:52) Training and onboarding new hires 

(01:24:41) Impact of ATT on performance marketing 

(01:25:56) The power of creative in ads 

(01:29:47) Using AI in performance marketing 

(01:37:16) Lightning round 

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Roger Martin is one of the world’s leading experts on strategy and the author of Playing to Win, one of the most beloved books on strategy. He’s written extensively for the Harvard Business Review; consulted for dozens of Fortune 500 companies, including P&G, Lego, and Ford; and written 11 other books. In our conversation, we discuss:

• The five key questions you need to answer to develop an effective strategy

• Why most companies get strategy wrong

• How to avoid “playing to play” instead of playing to win

• Real-world strategy examples from Procter & Gamble, Southwest Airlines, Lego, and Figma

• How to think about differentiation vs. low cost

• Shortcomings of current strategy education

• Much more

Correction: Roger pointed out that he made an error during our chat. When I asked him about Richard Rumelt (~16 mins), he thought I said Richard D'Aveni.

Brought to you by:

Webflow—The web experience platform

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Cycle—Your feedback hub, on autopilot

Find the transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

Where to find Roger Martin:

• X: https://x.com/RogerLMartin

• LinkedIn: https://www.linkedin.com/in/roger-martin-9916911a9/

• Website: https://rogerlmartin.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Roger’s background

(02:20) The importance of strategy

(07:00) Challenges in developing strategy

(08:30) Critique of modern strategy education

(14:00) Hamilton Helmer and Richard Rumelt

(17:40) Defining strategy

(19:12) The Strategy Choice Cascade

(23:20) Playing to win vs. playing to play

(24:57) Examples of strategic success

(30:49) Differentiation and moats

(40:23) Applying strategy to real-world scenarios

(43:47) Customer-centric strategy

(44:45) Defining the market and product

(45:59) Value chain and distribution

(48:28) Cost leadership vs. differentiation

(53:16) Capabilities and management systems

(57:14) Competitive advantage and market positioning

(01:02:41) Counterpositioning and fault lines

(01:05:53) Adapting to AI and market changes

(01:14:11) Betterment over perfection

(01:18:42) Final thoughts on strategy

Referenced:

• Nearly 10% of S&P 500 CEOs are alumni of Procter & Gamble: https://www.bizjournals.com/cincinnati/news/2023/02/06/10-of-s-p-500-ceos-pg.html

• FigJam: https://www.figma.com/figjam/

• Figma: https://www.figma.com/

• What Is Resource-Based Theory?: https://www.igi-global.com/dictionary/the-impact-of-technological-governance-and-political-capabilities-on-firms-performances-under-economic-turbulence/67915

• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487

• VRIO Framework Explained: https://strategicmanagementinsight.com/tools/vrio/

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Boston Consulting Group: https://www.bcg.com/

• Bruce Henderson: https://en.wikipedia.org/wiki/Bruce_Henderson

• Lego: https://www.lego.com

• Vanguard: https://investor.vanguard.com/

• Southwest Airlines: https://www.southwest.com/

• How Amazon Managed to Dethrone Walmart: https://www.nytimes.com/interactive/2021/08/20/technology/how-amazon-beat-walmart.html

• GM Lost a 10-Year Battle with Tesla, Pulling the Plug on a Long Line of EVs: https://www.forbes.com/sites/brookecrothers/2023/07/09/gm-killed-its-electric-cars-and-lost-a-10-year-battle-with-tesla/

• Westlaw: https://www.westlawinternational.com/

• What Is an Economic Moat? Why Warren Buffett Says It Matters for Investors: https://finance.yahoo.com/news/economic-moat-why-warren-buffett-160046125.html

• Salomon Brothers: https://en.wikipedia.org/wiki/Salomon_Brothers

• US Airways: https://en.wikipedia.org/wiki/US_Airways

• Four Seasons: https://www.fourseasons.com/

• Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell/

• Bill Gates on LinkedIn: https://www.linkedin.com/in/williamhgates/

• Mandarin Oriental: https://www.mandarinoriental.com/en/

• Continental Lite: https://en.wikipedia.org/wiki/Continental_Lite

• Ted (airline): https://en.wikipedia.org/wiki/Ted_(airline)

• Case Study: Oil of Olay: https://www.studocu.com/es/document/universidad-de-murcia/estrategia-de-marketing/case-study-old-of-olay/95079369

• AG Lafley on LinkedIn: https://www.linkedin.com/in/ag-lafley-2381b3201/

• Jack Bogle: https://en.wikipedia.org/wiki/John_C._Bogle

• Seven Ways Windows 95 Changed the World: https://www.forbes.com/sites/ianmorris/2015/08/24/windows-95-changed-the-world/

• Where to Start with Strategy? Focus on Betterment: https://rogermartin.medium.com/where-to-start-with-strategy-bae40506304c

• Brick by brick: The man who rebuilt the house of Lego shares his leadership secrets: https://www.washingtonpost.com/news/on-leadership/wp/2016/12/08/brick-by-brick-the-man-who-rebuilt-the-house-of-lego-shares-his-leadership-secrets/

A New Way to Think: Your Guide to Superior Management Effectiveness: https://www.amazon.com/New-Way-Think-Management-Effectiveness/dp/164782351X/

Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

The Design of Business: Why Design Thinking Is the Next Competitive Advantage: https://www.amazon.com/Design-Business-Thinking-Competitive-Advantage/dp/1422177807

The Opposable Mind: How Successful Leaders Win Through Integrative Thinking: https://www.amazon.com/Opposable-Mind-Successful-Integrative-Thinking/dp/1422118924

When More Is Not Better: Overcoming America’s Obsession with Economic Efficiency: https://www.amazon.com/When-More-Not-Better-Overcoming/dp/1647820065

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Roger Martin is one of the world’s leading experts on strategy and the author of Playing to Win, one of the most beloved books on strategy. He’s written extensively for the Harvard Business Review; consulted for dozens of Fortune 500 companies, including P&G, Lego, and Ford; and written 11 other books. In our conversation, we discuss:

• The five key questions you need to answer to develop an effective strategy

• Why most companies get strategy wrong

• How to avoid “playing to play” instead of playing to win

• Real-world strategy examples from Procter & Gamble, Southwest Airlines, Lego, and Figma

• How to think about differentiation vs. low cost

• Shortcomings of current strategy education

• Much more

Correction: Roger pointed out that he made an error during our chat. When I asked him about Richard Rumelt (~16 mins), he thought I said Richard D'Aveni.

Brought to you by:

Webflow—The web experience platform

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Cycle—Your feedback hub, on autopilot

Find the transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

Where to find Roger Martin:

• X: https://x.com/RogerLMartin

• LinkedIn: https://www.linkedin.com/in/roger-martin-9916911a9/

• Website: https://rogerlmartin.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Roger’s background

(02:20) The importance of strategy

(07:00) Challenges in developing strategy

(08:30) Critique of modern strategy education

(14:00) Hamilton Helmer and Richard Rumelt

(17:40) Defining strategy

(19:12) The Strategy Choice Cascade

(23:20) Playing to win vs. playing to play

(24:57) Examples of strategic success

(30:49) Differentiation and moats

(40:23) Applying strategy to real-world scenarios

(43:47) Customer-centric strategy

(44:45) Defining the market and product

(45:59) Value chain and distribution

(48:28) Cost leadership vs. differentiation

(53:16) Capabilities and management systems

(57:14) Competitive advantage and market positioning

(01:02:41) Counterpositioning and fault lines

(01:05:53) Adapting to AI and market changes

(01:14:11) Betterment over perfection

(01:18:42) Final thoughts on strategy

Referenced:

• Nearly 10% of S&P 500 CEOs are alumni of Procter & Gamble: https://www.bizjournals.com/cincinnati/news/2023/02/06/10-of-s-p-500-ceos-pg.html

• FigJam: https://www.figma.com/figjam/

• Figma: https://www.figma.com/

• What Is Resource-Based Theory?: https://www.igi-global.com/dictionary/the-impact-of-technological-governance-and-political-capabilities-on-firms-performances-under-economic-turbulence/67915

• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487

• VRIO Framework Explained: https://strategicmanagementinsight.com/tools/vrio/

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Boston Consulting Group: https://www.bcg.com/

• Bruce Henderson: https://en.wikipedia.org/wiki/Bruce_Henderson

• Lego: https://www.lego.com

• Vanguard: https://investor.vanguard.com/

• Southwest Airlines: https://www.southwest.com/

• How Amazon Managed to Dethrone Walmart: https://www.nytimes.com/interactive/2021/08/20/technology/how-amazon-beat-walmart.html

• GM Lost a 10-Year Battle with Tesla, Pulling the Plug on a Long Line of EVs: https://www.forbes.com/sites/brookecrothers/2023/07/09/gm-killed-its-electric-cars-and-lost-a-10-year-battle-with-tesla/

• Westlaw: https://www.westlawinternational.com/

• What Is an Economic Moat? Why Warren Buffett Says It Matters for Investors: https://finance.yahoo.com/news/economic-moat-why-warren-buffett-160046125.html

• Salomon Brothers: https://en.wikipedia.org/wiki/Salomon_Brothers

• US Airways: https://en.wikipedia.org/wiki/US_Airways

• Four Seasons: https://www.fourseasons.com/

• Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell/

• Bill Gates on LinkedIn: https://www.linkedin.com/in/williamhgates/

• Mandarin Oriental: https://www.mandarinoriental.com/en/

• Continental Lite: https://en.wikipedia.org/wiki/Continental_Lite

• Ted (airline): https://en.wikipedia.org/wiki/Ted_(airline)

• Case Study: Oil of Olay: https://www.studocu.com/es/document/universidad-de-murcia/estrategia-de-marketing/case-study-old-of-olay/95079369

• AG Lafley on LinkedIn: https://www.linkedin.com/in/ag-lafley-2381b3201/

• Jack Bogle: https://en.wikipedia.org/wiki/John_C._Bogle

• Seven Ways Windows 95 Changed the World: https://www.forbes.com/sites/ianmorris/2015/08/24/windows-95-changed-the-world/

• Where to Start with Strategy? Focus on Betterment: https://rogermartin.medium.com/where-to-start-with-strategy-bae40506304c

• Brick by brick: The man who rebuilt the house of Lego shares his leadership secrets: https://www.washingtonpost.com/news/on-leadership/wp/2016/12/08/brick-by-brick-the-man-who-rebuilt-the-house-of-lego-shares-his-leadership-secrets/

A New Way to Think: Your Guide to Superior Management Effectiveness: https://www.amazon.com/New-Way-Think-Management-Effectiveness/dp/164782351X/

Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

The Design of Business: Why Design Thinking Is the Next Competitive Advantage: https://www.amazon.com/Design-Business-Thinking-Competitive-Advantage/dp/1422177807

The Opposable Mind: How Successful Leaders Win Through Integrative Thinking: https://www.amazon.com/Opposable-Mind-Successful-Integrative-Thinking/dp/1422118924

When More Is Not Better: Overcoming America’s Obsession with Economic Efficiency: https://www.amazon.com/When-More-Not-Better-Overcoming/dp/1647820065

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Rory Sutherland is widely regarded as one of the most influential (and most entertaining) thinkers in marketing and behavioral science. He’s the vice chairman of Ogilvy UK, the author of Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life, and the founder of Nudgestock, the world’s biggest festival of behavioral science and creativity. He champions thinking from first principles and using human psychology—what he calls “thinking psycho-logically”—over mere logic. In our conversation, we cover:

• Why good products don’t always succeed, and bad ones don’t necessarily fail

• Why less functionality can sometimes be more valuable

• The importance of fame in building successful brands

• The importance of timing in product success

• The concept of “most advanced, yet acceptable”

• Why metrics-driven workplaces can be demotivating

• Lots of real-world case studies

• Much more

Note: We encountered some technical difficulties that led to less than ideal video quality for this episode, but the lessons from this conversation made it impossible for me to not publish it anyway. Thanks for your understanding and for bearing with the less-than-ideal video quality. 

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Cycle—Your feedback hub, on autopilot

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing

Where to find Rory Sutherland:

• X: https://x.com/rorysutherland

• LinkedIn: https://www.linkedin.com/in/rorysutherland

• Book: Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life: https://www.amazon.com/Alchemy-Curious-Science-Creating-Business/dp/006238841X

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Rory’s background

(02:37) The success and failure of products

(04:08) Why the urge to appear serious can be a disaster in marketing

(08:05) The role of distinctiveness in product design

(12:29) The MAYA principle

(15:50) How thinking irrationally can be advantageous

(17:40) The fault of multiple-choice tests

(21:31) Companies that have successfully implemented out-of-the-box thinking

(30:31) “Psycho-logical” thinking

(31:45) The hare and the dog metaphor

(38:51) Marketing’s crucial role in product adoption

(49:21) The quirks of Google Glass

(55:44) Survivorship bias

(56:09) Balancing rational ideas with irrational ideas

(01:06:19) The rise and fall of tech innovations

(01:09:54) Consistency, distinctiveness, and clarity

(01:21:12) Considering psychological, technological, and economic factors in parallel

(01:23:35) Where to find Rory

Referenced:

• Google Glass: https://en.wikipedia.org/wiki/Google_Glass

• Meta Portal TV: https://www.meta.com/portal/products/portal-tv/

• Rory’s quote in a LinkedIn post: https://www.linkedin.com/posts/brad-jackson-04766642_the-urge-to-appear-serious-is-a-disaster-activity-7093497742710210560-1LYN/

• The MAYA Principle: Design for the Future, but Balance It with Your Users’ Present: https://www.interaction-design.org/literature/article/design-for-the-future-but-balance-it-with-your-users-present

• Ogilvy: https://www.ogilvy.com/

• MCI: https://www.mci.world/

• Veuve Clicquot: https://en.wikipedia.org/wiki/Veuve_Clicquot

• Why do the French call the British ‘the roast beefs’?: http://news.bbc.co.uk/2/hi/2913151.stm

The Killing on Hulu: https://www.hulu.com/series/the-killing-f5da5c2d-4626-4ba9-bcf3-ff5f891771fb

• Original The Killing on BBC: https://www.bbc.co.uk/programmes/b017h7m1

• The Mandarin Oriental, Hong Kong: https://www.mandarinoriental.com/en/hong-kong/victoria-harbour

• SAT: https://satsuite.collegeboard.org/sat

• The Widening Racial Scoring Gap on the SAT College Admissions Test: https://www.jbhe.com/features/49_college_admissions-test.html

• What is the age of the captain?: https://www.icopilots.com/what-is-the-age-of-the-captain/

• Octopus Energy: https://octopus.energy/

• Kraken: https://octopusenergy.group/kraken-technologies

• Toby Shannan: https://theorg.com/org/shopify/org-chart/toby-shannan

• Dunbar’s number: Why we can only maintain 150 relationships: https://www.bbc.com/future/article/20191001-dunbars-number-why-we-can-only-maintain-150-relationships

• AO: https://ao.com/

• Zappos: https://www.zappos.com/

• Joe Cano on LinkedIn: https://www.linkedin.com/in/joeycano/

• John Ralston Saul’s website: https://www.johnralstonsaul.com/

Voltaire’s Bastards: The Dictatorship of Reason in the West: https://www.amazon.com/Voltaires-Bastards-Dictatorship-Reason-West/dp/0679748199

• Psycho-Logic: Why Too Much Logic Deters Magic: https://coffeeandjunk.com/psycho-logic/

• Herbert Simon’s Decision-Making Approach: https://bura.brunel.ac.uk/bitstream/2438/4995/1/Fulltext.pdf

• Robert Trivers’s website: https://roberttrivers.com/Welcome.html

• Crazy Ivan: https://jollycontrarian.com/index.php?title=Crazy_Ivan

• The Joys of Being a Late Tech Adopter: https://www.nytimes.com/2019/08/28/technology/personaltech/joys-late-tech-adopter.html

• Jean-Claude Van Damme: https://en.wikipedia.org/wiki/Jean-Claude_Van_Damme

• Tim Berners-Lee: https://en.wikipedia.org/wiki/Tim_Berners-Lee

• Edward Jenner and the history of smallpox and vaccination: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1200696/

• The real story behind penicillin: https://www.pbs.org/newshour/health/the-real-story-behind-the-worlds-first-antibiotic

• What Are Japanese Toilets?: https://www.bigbathroomshop.co.uk/info/blog/japanese-toilets/

• reMarkable: https://remarkable.com/

• Chumby: https://en.wikipedia.org/wiki/Chumby

• Survivorship bias: https://en.wikipedia.org/wiki/Survivorship_bias

• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive

• Marc Newson’s website: https://marc-newson.com/

• Designing Men: https://www.vanityfair.com/news/business/2013/11/jony-ive-marc-newson-design-auction

• Qantas A330: https://marc-newson.com/qantas-a330/

• Herodotus: https://en.wikipedia.org/wiki/Herodotus

• Big Decision? Consider It Both Drunk and Sober: https://www.forbes.com/sites/chunkamui/2016/03/22/wine-and-sleep-make-for-better-decisions/?sh=5c97fdc524b1

• How Henry Ford and Thomas Edison killed the electric car: https://www.speakev.com/threads/how-henry-ford-and-thomas-edison-killed-the-electric-car.4270/

• Watch Jay Leno get nostalgic and swoon over this 1909 EV: https://thenextweb.com/news/jay-leno-talk-about-electric-car-1909-baker

Jay Leno’s Garage: https://www.youtube.com/@jaylenosgarage

• Nudgestock: https://nudgestock.com/

• Akio Morita: https://en.wikipedia.org/wiki/Akio_Morita

• Don Norman on LinkedIn: https://www.linkedin.com/in/donnorman/

• What Makes Tesla’s Business Model Different: https://www.investopedia.com/articles/active-trading/072115/what-makes-teslas-business-model-different.asp

• Monica Lewinsky on X: https://x.com/MonicaLewinsky

Blindsight: The (Mostly) Hidden Ways Marketing Reshapes Our Brains: azon.com/Blindsight-Mostly-Hidden-Marketing-Reshapes-ebook/dp/B07ZKZ5DWF

Branding That Means Business: https://www.amazon.com/Branding-that-Means-Business-Economist-ebook/dp/B09QBCCH9N

• PwC: https://www.pwc.com

• Ryanair: https://www.ryanair.com

• British Airways: https://www.britishairways.com/

• Wrigley’s began as a soap business: know when to pivot: https://theamericangenius.com/entrepreneur/wrigleys-began-as-soap-know-when-to-pivot/

Transport for Humans: https://www.amazon.com/Transport-Humans-Perspectives-Pete-Dyson/dp/1913019357

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Rory Sutherland is widely regarded as one of the most influential (and most entertaining) thinkers in marketing and behavioral science. He’s the vice chairman of Ogilvy UK, the author of Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life, and the founder of Nudgestock, the world’s biggest festival of behavioral science and creativity. He champions thinking from first principles and using human psychology—what he calls “thinking psycho-logically”—over mere logic. In our conversation, we cover:

• Why good products don’t always succeed, and bad ones don’t necessarily fail

• Why less functionality can sometimes be more valuable

• The importance of fame in building successful brands

• The importance of timing in product success

• The concept of “most advanced, yet acceptable”

• Why metrics-driven workplaces can be demotivating

• Lots of real-world case studies

• Much more

Note: We encountered some technical difficulties that led to less than ideal video quality for this episode, but the lessons from this conversation made it impossible for me to not publish it anyway. Thanks for your understanding and for bearing with the less-than-ideal video quality. 

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Cycle—Your feedback hub, on autopilot

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing

Where to find Rory Sutherland:

• X: https://x.com/rorysutherland

• LinkedIn: https://www.linkedin.com/in/rorysutherland

• Book: Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life: https://www.amazon.com/Alchemy-Curious-Science-Creating-Business/dp/006238841X

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Rory’s background

(02:37) The success and failure of products

(04:08) Why the urge to appear serious can be a disaster in marketing

(08:05) The role of distinctiveness in product design

(12:29) The MAYA principle

(15:50) How thinking irrationally can be advantageous

(17:40) The fault of multiple-choice tests

(21:31) Companies that have successfully implemented out-of-the-box thinking

(30:31) “Psycho-logical” thinking

(31:45) The hare and the dog metaphor

(38:51) Marketing’s crucial role in product adoption

(49:21) The quirks of Google Glass

(55:44) Survivorship bias

(56:09) Balancing rational ideas with irrational ideas

(01:06:19) The rise and fall of tech innovations

(01:09:54) Consistency, distinctiveness, and clarity

(01:21:12) Considering psychological, technological, and economic factors in parallel

(01:23:35) Where to find Rory

Referenced:

• Google Glass: https://en.wikipedia.org/wiki/Google_Glass

• Meta Portal TV: https://www.meta.com/portal/products/portal-tv/

• Rory’s quote in a LinkedIn post: https://www.linkedin.com/posts/brad-jackson-04766642_the-urge-to-appear-serious-is-a-disaster-activity-7093497742710210560-1LYN/

• The MAYA Principle: Design for the Future, but Balance It with Your Users’ Present: https://www.interaction-design.org/literature/article/design-for-the-future-but-balance-it-with-your-users-present

• Ogilvy: https://www.ogilvy.com/

• MCI: https://www.mci.world/

• Veuve Clicquot: https://en.wikipedia.org/wiki/Veuve_Clicquot

• Why do the French call the British ‘the roast beefs’?: http://news.bbc.co.uk/2/hi/2913151.stm

The Killing on Hulu: https://www.hulu.com/series/the-killing-f5da5c2d-4626-4ba9-bcf3-ff5f891771fb

• Original The Killing on BBC: https://www.bbc.co.uk/programmes/b017h7m1

• The Mandarin Oriental, Hong Kong: https://www.mandarinoriental.com/en/hong-kong/victoria-harbour

• SAT: https://satsuite.collegeboard.org/sat

• The Widening Racial Scoring Gap on the SAT College Admissions Test: https://www.jbhe.com/features/49_college_admissions-test.html

• What is the age of the captain?: https://www.icopilots.com/what-is-the-age-of-the-captain/

• Octopus Energy: https://octopus.energy/

• Kraken: https://octopusenergy.group/kraken-technologies

• Toby Shannan: https://theorg.com/org/shopify/org-chart/toby-shannan

• Dunbar’s number: Why we can only maintain 150 relationships: https://www.bbc.com/future/article/20191001-dunbars-number-why-we-can-only-maintain-150-relationships

• AO: https://ao.com/

• Zappos: https://www.zappos.com/

• Joe Cano on LinkedIn: https://www.linkedin.com/in/joeycano/

• John Ralston Saul’s website: https://www.johnralstonsaul.com/

Voltaire’s Bastards: The Dictatorship of Reason in the West: https://www.amazon.com/Voltaires-Bastards-Dictatorship-Reason-West/dp/0679748199

• Psycho-Logic: Why Too Much Logic Deters Magic: https://coffeeandjunk.com/psycho-logic/

• Herbert Simon’s Decision-Making Approach: https://bura.brunel.ac.uk/bitstream/2438/4995/1/Fulltext.pdf

• Robert Trivers’s website: https://roberttrivers.com/Welcome.html

• Crazy Ivan: https://jollycontrarian.com/index.php?title=Crazy_Ivan

• The Joys of Being a Late Tech Adopter: https://www.nytimes.com/2019/08/28/technology/personaltech/joys-late-tech-adopter.html

• Jean-Claude Van Damme: https://en.wikipedia.org/wiki/Jean-Claude_Van_Damme

• Tim Berners-Lee: https://en.wikipedia.org/wiki/Tim_Berners-Lee

• Edward Jenner and the history of smallpox and vaccination: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1200696/

• The real story behind penicillin: https://www.pbs.org/newshour/health/the-real-story-behind-the-worlds-first-antibiotic

• What Are Japanese Toilets?: https://www.bigbathroomshop.co.uk/info/blog/japanese-toilets/

• reMarkable: https://remarkable.com/

• Chumby: https://en.wikipedia.org/wiki/Chumby

• Survivorship bias: https://en.wikipedia.org/wiki/Survivorship_bias

• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive

• Marc Newson’s website: https://marc-newson.com/

• Designing Men: https://www.vanityfair.com/news/business/2013/11/jony-ive-marc-newson-design-auction

• Qantas A330: https://marc-newson.com/qantas-a330/

• Herodotus: https://en.wikipedia.org/wiki/Herodotus

• Big Decision? Consider It Both Drunk and Sober: https://www.forbes.com/sites/chunkamui/2016/03/22/wine-and-sleep-make-for-better-decisions/?sh=5c97fdc524b1

• How Henry Ford and Thomas Edison killed the electric car: https://www.speakev.com/threads/how-henry-ford-and-thomas-edison-killed-the-electric-car.4270/

• Watch Jay Leno get nostalgic and swoon over this 1909 EV: https://thenextweb.com/news/jay-leno-talk-about-electric-car-1909-baker

Jay Leno’s Garage: https://www.youtube.com/@jaylenosgarage

• Nudgestock: https://nudgestock.com/

• Akio Morita: https://en.wikipedia.org/wiki/Akio_Morita

• Don Norman on LinkedIn: https://www.linkedin.com/in/donnorman/

• What Makes Tesla’s Business Model Different: https://www.investopedia.com/articles/active-trading/072115/what-makes-teslas-business-model-different.asp

• Monica Lewinsky on X: https://x.com/MonicaLewinsky

Blindsight: The (Mostly) Hidden Ways Marketing Reshapes Our Brains: azon.com/Blindsight-Mostly-Hidden-Marketing-Reshapes-ebook/dp/B07ZKZ5DWF

Branding That Means Business: https://www.amazon.com/Branding-that-Means-Business-Economist-ebook/dp/B09QBCCH9N

• PwC: https://www.pwc.com

• Ryanair: https://www.ryanair.com

• British Airways: https://www.britishairways.com/

• Wrigley’s began as a soap business: know when to pivot: https://theamericangenius.com/entrepreneur/wrigleys-began-as-soap-know-when-to-pivot/

Transport for Humans: https://www.amazon.com/Transport-Humans-Perspectives-Pete-Dyson/dp/1913019357

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jessica Lachs is the global head of analytics and data science at DoorDash, where she’s built one of the largest and most respected data organizations in tech. In her more than 10 years at DoorDash, she has served as the first general manager, responsible for launching new markets; the head of business ops and analytics; and the VP of analytics and data science. Previously, Jessica founded GiftSimple, a social gifting startup, and started her career at Lehman Brothers as an investment banking analyst. In our conversation, she shares:

• How to structure and scale a high-impact analytics organization

• Centralized vs. decentralized data teams

• How to pick the right metric and aligning incentives

• Advice for data people on how and when to push back

• Lessons learned from building a global data team

• How to foster a culture of extreme ownership

• The role of AI in improving analytics team productivity

• Advice for aspiring data leaders without formal training

Brought to you by:

Webflow—The web experience platform

Anvil—The fastest way to build software for documents

Attio—The powerful, flexible CRM for fast-growing startups

Find the transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-data-org-jessica-lachs

Where to find Jessica Lachs:

• X: https://x.com/jesslachs

• LinkedIn: https://www.linkedin.com/in/jessica-lachs/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jessica’s background

(04:59) Centralized vs. embedded analytics teams

(10:52) The benefits of a centralized analytics team

(15:10) Balancing proactive and reactive work

(20:45) Advice on how to push back effectively

(24:20) Hiring for curiosity and problem solving

(28:57) Coming from a non-traditional background

(34:40) The early days and culture at DoorDash

(40:39) Encouraging cross-functional roles

(44:39) Defining effective metrics

(46:30) Simplifying metrics for better outcomes

(55:28) Focusing on edge cases and fail states

(01:00:12) Managing a global data organization

(01:02:31) Leveraging AI for productivity

(01:05:25) Building diverse and skilled data teams

(01:08:40) Lightning round

Referenced:

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Riley Newman on LinkedIn: https://www.linkedin.com/in/rileynewman/

• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

• Imposter Syndrome: Why You May Feel Like a Fraud: https://www.verywellmind.com/imposter-syndrome-and-social-anxiety-disorder-4156469

• Stanley Tang on LinkedIn: https://www.linkedin.com/in/stanleytang/

• Andy Fang on LinkedIn: https://www.linkedin.com/in/fangsterr/

• Evan Moore on LinkedIn: https://www.linkedin.com/in/evanmoore/

• How WeDash became the flagship employee program for DoorDash: https://careers.doordash.com/blog/wedash-doordash-employee-program-how-does-it-work

• Leading with empathy | Keith Yandell (DoorDash, Uber): https://www.lennysnewsletter.com/p/leading-with-empathy-keith-yandell

The Rose Code: https://www.amazon.com/Rose-Code-Novel-Kate-Quinn/dp/006305941X

• Libby app: https://libbyapp.com/

The West Wing on Prime: https://www.amazon.com/West-Wing-Complete-First-Season/dp/B000KZPG04

Alias on Prime: https://www.amazon.com/Alias-Season-1/dp/B00748O13S

• Joseon sunscreens: https://beautyofjoseon.com/

• Innisfree sunscreens: https://us.innisfree.com/

• John Steinbeck quote: https://www.brainyquote.com/quotes/john_steinbeck_103825

• Vanessa Roberts on LinkedIn: https://www.linkedin.com/in/vanessa-roberts-b8a509a/

• Tia Sherringham on LinkedIn: https://www.linkedin.com/in/tiasherringham/

• Elizabeth Jarvis-Shean on LinkedIn: https://www.linkedin.com/in/elizabeth-jarvis-shean-141a7966/

• Regina (Gina) Tarone on LinkedIn: https://www.linkedin.com/in/regina-tarone-a565a2/overlay/about-this-profile/

• My Journey (Part 1): I have a job that I would never be hired for: https://www.linkedin.com/posts/jessica-lachs_anniversary-datascience-finance-activity-7216912300056727553-mEv6/?utm_source=share&utm_medium=member_desktop

• Starting an Analytics Org From Scratch — Lessons From a Decade at DoorDash: https://review.firstround.com/starting-an-analytics-org-from-scratch-lessons-from-a-decade-at-doordash/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jessica Lachs is the global head of analytics and data science at DoorDash, where she’s built one of the largest and most respected data organizations in tech. In her more than 10 years at DoorDash, she has served as the first general manager, responsible for launching new markets; the head of business ops and analytics; and the VP of analytics and data science. Previously, Jessica founded GiftSimple, a social gifting startup, and started her career at Lehman Brothers as an investment banking analyst. In our conversation, she shares:

• How to structure and scale a high-impact analytics organization

• Centralized vs. decentralized data teams

• How to pick the right metric and aligning incentives

• Advice for data people on how and when to push back

• Lessons learned from building a global data team

• How to foster a culture of extreme ownership

• The role of AI in improving analytics team productivity

• Advice for aspiring data leaders without formal training

Brought to you by:

Webflow—The web experience platform

Anvil—The fastest way to build software for documents

Attio—The powerful, flexible CRM for fast-growing startups

Find the transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-data-org-jessica-lachs

Where to find Jessica Lachs:

• X: https://x.com/jesslachs

• LinkedIn: https://www.linkedin.com/in/jessica-lachs/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jessica’s background

(04:59) Centralized vs. embedded analytics teams

(10:52) The benefits of a centralized analytics team

(15:10) Balancing proactive and reactive work

(20:45) Advice on how to push back effectively

(24:20) Hiring for curiosity and problem solving

(28:57) Coming from a non-traditional background

(34:40) The early days and culture at DoorDash

(40:39) Encouraging cross-functional roles

(44:39) Defining effective metrics

(46:30) Simplifying metrics for better outcomes

(55:28) Focusing on edge cases and fail states

(01:00:12) Managing a global data organization

(01:02:31) Leveraging AI for productivity

(01:05:25) Building diverse and skilled data teams

(01:08:40) Lightning round

Referenced:

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Riley Newman on LinkedIn: https://www.linkedin.com/in/rileynewman/

• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

• Imposter Syndrome: Why You May Feel Like a Fraud: https://www.verywellmind.com/imposter-syndrome-and-social-anxiety-disorder-4156469

• Stanley Tang on LinkedIn: https://www.linkedin.com/in/stanleytang/

• Andy Fang on LinkedIn: https://www.linkedin.com/in/fangsterr/

• Evan Moore on LinkedIn: https://www.linkedin.com/in/evanmoore/

• How WeDash became the flagship employee program for DoorDash: https://careers.doordash.com/blog/wedash-doordash-employee-program-how-does-it-work

• Leading with empathy | Keith Yandell (DoorDash, Uber): https://www.lennysnewsletter.com/p/leading-with-empathy-keith-yandell

The Rose Code: https://www.amazon.com/Rose-Code-Novel-Kate-Quinn/dp/006305941X

• Libby app: https://libbyapp.com/

The West Wing on Prime: https://www.amazon.com/West-Wing-Complete-First-Season/dp/B000KZPG04

Alias on Prime: https://www.amazon.com/Alias-Season-1/dp/B00748O13S

• Joseon sunscreens: https://beautyofjoseon.com/

• Innisfree sunscreens: https://us.innisfree.com/

• John Steinbeck quote: https://www.brainyquote.com/quotes/john_steinbeck_103825

• Vanessa Roberts on LinkedIn: https://www.linkedin.com/in/vanessa-roberts-b8a509a/

• Tia Sherringham on LinkedIn: https://www.linkedin.com/in/tiasherringham/

• Elizabeth Jarvis-Shean on LinkedIn: https://www.linkedin.com/in/elizabeth-jarvis-shean-141a7966/

• Regina (Gina) Tarone on LinkedIn: https://www.linkedin.com/in/regina-tarone-a565a2/overlay/about-this-profile/

• My Journey (Part 1): I have a job that I would never be hired for: https://www.linkedin.com/posts/jessica-lachs_anniversary-datascience-finance-activity-7216912300056727553-mEv6/?utm_source=share&utm_medium=member_desktop

• Starting an Analytics Org From Scratch — Lessons From a Decade at DoorDash: https://review.firstround.com/starting-an-analytics-org-from-scratch-lessons-from-a-decade-at-doordash/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jeff Weinstein is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss:

• The power of customer obsession and how to operationalize it in the product development process

• How to pick the right metrics and use them to drive impact

• Techniques for getting things done at big companies

• A group practice Jeff started to uplevel product craft, called Study Group

• The story behind Stripe Atlas and its mission to increase entrepreneurship globally

• Lessons from working with the founders of Stripe

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Cycle—Your feedback hub, on autopilot

Anvil—The fastest way to build software for documents

Find the transcript at: https://www.lennysnewsletter.com/p/creating-a-culture-of-excellence

Where to find Jeff Weinstein:

• X: https://x.com/jeff_weinstein

• LinkedIn: https://www.linkedin.com/in/jeffwweinstein/

• Email: jweinstein@gmail.com

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jeff’s background 

(10:16)  The “go, go, go ASAP + optimistic, long-term compounding” approach

(15:38) The importance of craft and quality

(24:15) Effective customer communication strategies

(28:57) The importance of speed in customer interactions 

(33:19) Narrowing your focus

(36:53) Why you should pay attention only to paying-customer feedback

(40:24) Practicing silence when communicating 

(45:33) The role of metrics in product success

(54:08) Empowering teams with a single metric

(58:23) Picking the right metric for your audience

(01:05:10) The importance of metric hygiene

(01:11:33) How Stripe uses “study groups” for product improvement

(01:37:20) Stripe’s Atlas: simplifying company formation

(01:50:38) Automation and operational efficiency

(01:55:13) Diversity and team building

(02:03:09) Building new products within a large company

(02:21:10) Lightning round

Referenced:

• Atlas: https://stripe.com/atlas

• Stripe: https://stripe.com/

• SQL: https://en.wikipedia.org/wiki/SQL

• GitHub: https://github.com/

• Linear: https://linear.app/

• Figma: https://www.figma.com/

• Jeff’s tweet about Stripe’s bug-finder program: https://x.com/jeff_weinstein/status/1777487507934040300

• The “Collison installation”: https://news.ycombinator.com/item?id=18400504

• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p

• Fidelity: https://www.fidelity.com/

• 83(b) election: https://docs.stripe.com/atlas/83b-election

• Jeff’s tweet about Atlas’s NPS score: https://x.com/jeff_weinstein/status/1788644576330469638

• What is a Delaware corporation? Here’s what makes this state so attractive to businesses: https://stripe.com/resources/more/what-is-a-delaware-corporation

• Incorporating in Delaware explained: Why it’s such a popular option for businesses: https://stripe.com/resources/more/incorporating-in-delaware-explained

• 7 of Pixar’s Best Storyboard Examples and the Stories Behind Them: https://boords.com/blog/7-of-pixars-best-storyboard-examples-and-the-stories-behind-them

• Alex Kehayias on LinkedIn: https://www.linkedin.com/in/alexkehayias/

• Patrick McKenzie on LinkedIn: https://www.linkedin.com/in/patrickmckenzie/

• AngelList: https://www.angellist.com/

• Dan Hightower on LinkedIn: https://www.linkedin.com/in/danhighto/

• Stripe Atlas perks partners: https://support.stripe.com/questions/stripe-atlas-perks-partners

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

Orbiting the Giant Hairball: A Corporate Fool’s Guide to Surviving with Grace: https://www.amazon.com/Orbiting-Giant-Hairball-Corporate-Surviving/dp/0670879835

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Box: https://www.box.com/

• Patrick Collison on X: https://x.com/patrickc

How to with John Wilson on HBO: https://www.hbo.com/how-to-with-john-wilson

The Quiet Girl on Hulu: https://www.hulu.com/movie/the-quiet-girl-b50a4b8e-d3ff-4635-b806-5e7dbd292ca4

• Raycast: https://www.raycast.com/

• Quicksilver: https://qsapp.com/

• Alfred: https://www.alfredapp.com/help/workflows/automations/

• CleanShot: https://cleanshot.com/

• John Collison on X: https://x.com/collision

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jeff Weinstein is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss:

• The power of customer obsession and how to operationalize it in the product development process

• How to pick the right metrics and use them to drive impact

• Techniques for getting things done at big companies

• A group practice Jeff started to uplevel product craft, called Study Group

• The story behind Stripe Atlas and its mission to increase entrepreneurship globally

• Lessons from working with the founders of Stripe

Brought to you by:

Pendo—The only all-in-one product experience platform for any type of application

Cycle—Your feedback hub, on autopilot

Anvil—The fastest way to build software for documents

Find the transcript at: https://www.lennysnewsletter.com/p/creating-a-culture-of-excellence

Where to find Jeff Weinstein:

• X: https://x.com/jeff_weinstein

• LinkedIn: https://www.linkedin.com/in/jeffwweinstein/

• Email: jweinstein@gmail.com

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jeff’s background 

(10:16)  The “go, go, go ASAP + optimistic, long-term compounding” approach

(15:38) The importance of craft and quality

(24:15) Effective customer communication strategies

(28:57) The importance of speed in customer interactions 

(33:19) Narrowing your focus

(36:53) Why you should pay attention only to paying-customer feedback

(40:24) Practicing silence when communicating 

(45:33) The role of metrics in product success

(54:08) Empowering teams with a single metric

(58:23) Picking the right metric for your audience

(01:05:10) The importance of metric hygiene

(01:11:33) How Stripe uses “study groups” for product improvement

(01:37:20) Stripe’s Atlas: simplifying company formation

(01:50:38) Automation and operational efficiency

(01:55:13) Diversity and team building

(02:03:09) Building new products within a large company

(02:21:10) Lightning round

Referenced:

• Atlas: https://stripe.com/atlas

• Stripe: https://stripe.com/

• SQL: https://en.wikipedia.org/wiki/SQL

• GitHub: https://github.com/

• Linear: https://linear.app/

• Figma: https://www.figma.com/

• Jeff’s tweet about Stripe’s bug-finder program: https://x.com/jeff_weinstein/status/1777487507934040300

• The “Collison installation”: https://news.ycombinator.com/item?id=18400504

• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p

• Fidelity: https://www.fidelity.com/

• 83(b) election: https://docs.stripe.com/atlas/83b-election

• Jeff’s tweet about Atlas’s NPS score: https://x.com/jeff_weinstein/status/1788644576330469638

• What is a Delaware corporation? Here’s what makes this state so attractive to businesses: https://stripe.com/resources/more/what-is-a-delaware-corporation

• Incorporating in Delaware explained: Why it’s such a popular option for businesses: https://stripe.com/resources/more/incorporating-in-delaware-explained

• 7 of Pixar’s Best Storyboard Examples and the Stories Behind Them: https://boords.com/blog/7-of-pixars-best-storyboard-examples-and-the-stories-behind-them

• Alex Kehayias on LinkedIn: https://www.linkedin.com/in/alexkehayias/

• Patrick McKenzie on LinkedIn: https://www.linkedin.com/in/patrickmckenzie/

• AngelList: https://www.angellist.com/

• Dan Hightower on LinkedIn: https://www.linkedin.com/in/danhighto/

• Stripe Atlas perks partners: https://support.stripe.com/questions/stripe-atlas-perks-partners

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

Orbiting the Giant Hairball: A Corporate Fool’s Guide to Surviving with Grace: https://www.amazon.com/Orbiting-Giant-Hairball-Corporate-Surviving/dp/0670879835

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Box: https://www.box.com/

• Patrick Collison on X: https://x.com/patrickc

How to with John Wilson on HBO: https://www.hbo.com/how-to-with-john-wilson

The Quiet Girl on Hulu: https://www.hulu.com/movie/the-quiet-girl-b50a4b8e-d3ff-4635-b806-5e7dbd292ca4

• Raycast: https://www.raycast.com/

• Quicksilver: https://qsapp.com/

• Alfred: https://www.alfredapp.com/help/workflows/automations/

• CleanShot: https://cleanshot.com/

• John Collison on X: https://x.com/collision

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about:

• The three elements of breakthrough startup ideas

• Why you need to both think and act differently

• How to avoid the “comparison trap” and “conformity trap”

• The importance of movements, storytelling, and healthy disagreeableness in startup success

• How to apply pattern-breaking principles within large companies

• Mike’s one piece of advice for founders

• Much more

Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny.

Brought to you by:

Enterpret—Transform customer feedback into product growth

Anvil—The fastest way to build software for documents

Webflow—The web experience platform

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr

Where to find Mike Maples, Jr.:

• X: https://x.com/m2jr

• LinkedIn: https://www.linkedin.com/in/maples/

• Substack: https://greatness.substack.com/

• Website: https://www.floodgate.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Mike’s background

(03:10) The inspiration behind Pattern Breakers

(08:09) Uncovering startup insights

(11:37) A quick summary of Pattern Breakers

(13:52) Coming up with an idea

(15:30) Inflections

(17:09) Examples of inflections

(28:10) Insights

(36:58) The power of surprises

(47:36) Founder-future fit

(55:33) Advice for aspiring founders

(56:41) Living in the future: valid opinions

(55:34) Case study: Maddie Hall and Living Carbon

(58:40) Identifying lighthouse customers

(01:00:53) The importance of desperation in customer needs

(01:03:57) Creating movements and storytelling

(01:24:22) The role of disagreeableness in startups

(01:34:42) Applying these principles within a company

(01:40:43) Lightning round

Referenced:

Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355

• Justin.tv: https://en.wikipedia.org/wiki/Justin.tv

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354

• Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/

• The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/

• The Craigslist Killers: https://www.gq.com/story/craigslist-killers

• The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

• Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/

The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669

• Scott Cook: https://www.forbes.com/profile/scott-cook/

• Chegg: https://www.chegg.com/

• Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/

• Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/

• Okta: https://www.okta.com/

• The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/

• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/

• Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/

• Paul Allen’s website: https://paulallen.com/

• Louis Pasteur quote: https://www.forbes.com/quotes/6145/

• What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly

• Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/

• Living Carbon: https://www.livingcarbon.com

• Zenefits (now Trinet): https://connect.trinet.com/

• Sam Altman on X: https://x.com/sama

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Horsley Bridge Partners: https://www.horsleybridge.com/

• David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen

• Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/

• Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/

• John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/

• Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how

• Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4

Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/

• Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

• Figma: https://www.figma.com/

• Atlassian: https://www.atlassian.com/

• Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/

• Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L

Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355

• Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y

Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011

Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672

• Montblanc fountain pens: https://www.montblanc.com/en-us

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about:

• The three elements of breakthrough startup ideas

• Why you need to both think and act differently

• How to avoid the “comparison trap” and “conformity trap”

• The importance of movements, storytelling, and healthy disagreeableness in startup success

• How to apply pattern-breaking principles within large companies

• Mike’s one piece of advice for founders

• Much more

Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny.

Brought to you by:

Enterpret—Transform customer feedback into product growth

Anvil—The fastest way to build software for documents

Webflow—The web experience platform

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr

Where to find Mike Maples, Jr.:

• X: https://x.com/m2jr

• LinkedIn: https://www.linkedin.com/in/maples/

• Substack: https://greatness.substack.com/

• Website: https://www.floodgate.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Mike’s background

(03:10) The inspiration behind Pattern Breakers

(08:09) Uncovering startup insights

(11:37) A quick summary of Pattern Breakers

(13:52) Coming up with an idea

(15:30) Inflections

(17:09) Examples of inflections

(28:10) Insights

(36:58) The power of surprises

(47:36) Founder-future fit

(55:33) Advice for aspiring founders

(56:41) Living in the future: valid opinions

(55:34) Case study: Maddie Hall and Living Carbon

(58:40) Identifying lighthouse customers

(01:00:53) The importance of desperation in customer needs

(01:03:57) Creating movements and storytelling

(01:24:22) The role of disagreeableness in startups

(01:34:42) Applying these principles within a company

(01:40:43) Lightning round

Referenced:

Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355

• Justin.tv: https://en.wikipedia.org/wiki/Justin.tv

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354

• Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/

• The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/

• The Craigslist Killers: https://www.gq.com/story/craigslist-killers

• The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

• Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/

The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669

• Scott Cook: https://www.forbes.com/profile/scott-cook/

• Chegg: https://www.chegg.com/

• Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/

• Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/

• Okta: https://www.okta.com/

• The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/

• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/

• Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/

• Paul Allen’s website: https://paulallen.com/

• Louis Pasteur quote: https://www.forbes.com/quotes/6145/

• What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly

• Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/

• Living Carbon: https://www.livingcarbon.com

• Zenefits (now Trinet): https://connect.trinet.com/

• Sam Altman on X: https://x.com/sama

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Horsley Bridge Partners: https://www.horsleybridge.com/

• David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen

• Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/

• Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/

• John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/

• Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how

• Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4

Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/

• Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

• Figma: https://www.figma.com/

• Atlassian: https://www.atlassian.com/

• Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/

• Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L

Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355

• Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y

Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011

Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672

• Montblanc fountain pens: https://www.montblanc.com/en-us

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into:

• How intuition and product taste drive Dylan’s decision-making

• The challenge of keeping things simple

• Dylan’s thoughts on the future of product management

• Lessons from Figma’s early days

• How Figma built their initial user base

• Dylan’s journey from intern to CEO of a 1,000+-person company

• The future of design tools and AI

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Anvil—The fastest way to build software for documents

User Testing—Human understanding. Human experiences.

Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

Where to find Dylan Field:

• X: https://x.com/zoink?lang=en

• LinkedIn: https://www.linkedin.com/in/dylanfield/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction

(01:11) Welcoming Dylan Field

(02:36) Highlights and surprises from Config

(06:58) The philosophy of design

(08:01) Raccoon feet and muffin hands

(09:57) Building and refining intuition and product taste

(12:50) How to influence leadership

(16:14) The role of product managers

(21:12) The future of product management

(22:20) The importance of simplicity in design

(26:10) The long road to Figma’s launch

(27:44) Advice for aspiring entrepreneurs

(29:07) Knowing when it’s time to ship

(30:39) Early user acquisition strategies

(35:50) Spotting trends and future innovations

(39:20) Reflections on leadership and growth

(43:16) Lightning round

Referenced:

• Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/

• Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w

• Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages

• Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o

• An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/

• Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

• FigJam: https://www.figma.com/figjam/

• Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/

• Coda: https://coda.io/

• Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/

• Websim: https://websim.ai/

• eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into:

• How intuition and product taste drive Dylan’s decision-making

• The challenge of keeping things simple

• Dylan’s thoughts on the future of product management

• Lessons from Figma’s early days

• How Figma built their initial user base

• Dylan’s journey from intern to CEO of a 1,000+-person company

• The future of design tools and AI

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Anvil—The fastest way to build software for documents

User Testing—Human understanding. Human experiences.

Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

Where to find Dylan Field:

• X: https://x.com/zoink?lang=en

• LinkedIn: https://www.linkedin.com/in/dylanfield/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction

(01:11) Welcoming Dylan Field

(02:36) Highlights and surprises from Config

(06:58) The philosophy of design

(08:01) Raccoon feet and muffin hands

(09:57) Building and refining intuition and product taste

(12:50) How to influence leadership

(16:14) The role of product managers

(21:12) The future of product management

(22:20) The importance of simplicity in design

(26:10) The long road to Figma’s launch

(27:44) Advice for aspiring entrepreneurs

(29:07) Knowing when it’s time to ship

(30:39) Early user acquisition strategies

(35:50) Spotting trends and future innovations

(39:20) Reflections on leadership and growth

(43:16) Lightning round

Referenced:

• Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/

• Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w

• Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages

• Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o

• An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/

• Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

• FigJam: https://www.figma.com/figjam/

• Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/

• Coda: https://coda.io/

• Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/

• Websim: https://websim.ai/

• eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss:

• How Jessica gained the affectionate title of the “social radar”

• Why defensive founders are a red flag

• How to develop your social radar

• What she looks for in founders during YC interviews

• How YC’s early inexperience in angel investing led to the batch model

• Her favorite stories from interviews with Airbnb, Rippling, and more

• Lessons learned from hosting her own podcast

• Much more

Brought to you by:

Enterpret—Transform customer feedback into product growth

Anvil—The fastest way to build software for documents

Vanta—Automate compliance. Simplify security

Find the transcript at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

Where to find Jessica Livingston:

• X: https://x.com/jesslivingston

• LinkedIn: https://www.linkedin.com/in/jessicalivingston1/

• Podcast: https://www.thesocialradars.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jessica’s background

(02:42) Thoughts on being under-recognized

(07:52) Jessica’s superpower: the social radar

(15:11) Evaluating founders: key traits and red flags

(21:00) The Airbnb story: a lesson in hustle and determination

(25:57) A YC success story

(28:26) The importance of earnestness

(32:45) Confidence vs. defensiveness

(34:43) Commitment and co-founder disputes

(37:46) Relentless resourcefulness

(40:00) Jessica’s social radar: origins and insights

(43:24) Honing her social radar skills

(45:44) Conviction and scams: a Y Combinator story

(46:50) The interview process: challenges and insights

(48:20) Operationalizing founder evaluation

(49:38) Advice for building social radar skills

(52:08) The “Reading the Mind in the Eyes” quiz

(55:19) Jessica’s podcast: The Social Radars

(01:00:34) Lessons from podcasting and interviewing

(01:09:58) Lightning round

Referenced:

• Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html

• Paul Graham on X: https://x.com/paulg

• Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris

• Trevor Blackwell on X: https://x.com/tlbtlbtlb

• Y Combinator: https://www.ycombinator.com/

• “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal

• Patrick Collison on X: https://x.com/patrickc

• John Collison on X: https://x.com/collision

• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

• Nate Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/

• Zenefits: https://connect.trinet.com/hr-platform

• Goat: https://www.goat.com/

• Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

• Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

•Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html

• Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691

• SmartLess podcast: https://www.smartless.com

• Jason Bateman on X: https://x.com/batemanjason

• Will Arnett on X: https://x.com/arnettwill

• Sean Hayes on X: https://x.com/seanhayes

• The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash

• The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb

• The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe

• The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase

• The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch

• The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb

• The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab

Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788

• Startup School: https://www.startupschool.org/

• The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling

• Rippling: https://www.rippling.com/

Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957

Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06

Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/

Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/

My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522

Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R

Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273

Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone

• Sam Altman on X: https://x.com/sama

• Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/

• Alexis Ohanian on X: https://x.com/alexisohanian

• Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/

• Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/

• Charles River Venture: https://www.crv.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss:

• How Jessica gained the affectionate title of the “social radar”

• Why defensive founders are a red flag

• How to develop your social radar

• What she looks for in founders during YC interviews

• How YC’s early inexperience in angel investing led to the batch model

• Her favorite stories from interviews with Airbnb, Rippling, and more

• Lessons learned from hosting her own podcast

• Much more

Brought to you by:

Enterpret—Transform customer feedback into product growth

Anvil—The fastest way to build software for documents

Vanta—Automate compliance. Simplify security

Find the transcript at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

Where to find Jessica Livingston:

• X: https://x.com/jesslivingston

• LinkedIn: https://www.linkedin.com/in/jessicalivingston1/

• Podcast: https://www.thesocialradars.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jessica’s background

(02:42) Thoughts on being under-recognized

(07:52) Jessica’s superpower: the social radar

(15:11) Evaluating founders: key traits and red flags

(21:00) The Airbnb story: a lesson in hustle and determination

(25:57) A YC success story

(28:26) The importance of earnestness

(32:45) Confidence vs. defensiveness

(34:43) Commitment and co-founder disputes

(37:46) Relentless resourcefulness

(40:00) Jessica’s social radar: origins and insights

(43:24) Honing her social radar skills

(45:44) Conviction and scams: a Y Combinator story

(46:50) The interview process: challenges and insights

(48:20) Operationalizing founder evaluation

(49:38) Advice for building social radar skills

(52:08) The “Reading the Mind in the Eyes” quiz

(55:19) Jessica’s podcast: The Social Radars

(01:00:34) Lessons from podcasting and interviewing

(01:09:58) Lightning round

Referenced:

• Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html

• Paul Graham on X: https://x.com/paulg

• Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris

• Trevor Blackwell on X: https://x.com/tlbtlbtlb

• Y Combinator: https://www.ycombinator.com/

• “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal

• Patrick Collison on X: https://x.com/patrickc

• John Collison on X: https://x.com/collision

• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

• Nate Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/

• Zenefits: https://connect.trinet.com/hr-platform

• Goat: https://www.goat.com/

• Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

• Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

•Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html

• Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691

• SmartLess podcast: https://www.smartless.com

• Jason Bateman on X: https://x.com/batemanjason

• Will Arnett on X: https://x.com/arnettwill

• Sean Hayes on X: https://x.com/seanhayes

• The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash

• The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb

• The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe

• The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase

• The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch

• The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb

• The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab

Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788

• Startup School: https://www.startupschool.org/

• The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling

• Rippling: https://www.rippling.com/

Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957

Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06

Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/

Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/

My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522

Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R

Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273

Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone

• Sam Altman on X: https://x.com/sama

• Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/

• Alexis Ohanian on X: https://x.com/alexisohanian

• Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/

• Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/

• Charles River Venture: https://www.crv.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ami Vora is the Chief Product Officer of Faire, which connects independent retailers and brands around the world. Before Faire, Ami spent over 15 years at Meta, including as VP of Product and Design for WhatsApp (2B+ users), VP of Product for Facebook’s ads system (now $130B of annual revenue), and director at Instagram. She began her career working on developer tools at Microsoft. In our conversation, we discuss:

• Why execution eats strategy for breakfast

• Using metaphor to rally teams around one shared goal

• How to build cross-functional relationships

• “Dinosaur brain,” “Toddler soccer,” and the “hill climbing” metaphors

• A tactic for handling disagreement

• Tips for working well with product-minded founders as a product leader

• The story of Ami’s incredible 15-year journey from temp to VP at Meta

• Much more

Brought to you by:

Sidebar—Accelerate your career by surrounding yourself with extraordinary peers.

Anvil—The fastest way to build software for documents.

User Testing—Human understanding. Human experiences.

Find the transcript at: https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

Where to find Ami Vora:

• LinkedIn: https://www.linkedin.com/in/amvora/

• Substack: https://amivora.substack.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Ami’s background

(02:00) The myth of perfection in success

(07:55) Emotionally connecting with the job

(09:55) Embracing curiosity in moments of challenge

(13:16) Thinking in feedback loops

(17:17) The “dinosaur brain” metaphor in product reviews

(20:20) Strategies for conducting effective product reviews

(26:33) Using metaphors and imagery to communicate your vision

(29:35) The power of having a shared narrative

(31:55) WhatsApp: an example of metaphor in action

(34:44) Emulating people that inspire you

(36:19) WhatsApp video calling

(37:35) Why execution is greater than strategy

(41:36) Time allotment for strategy vs. execution

(45:10) How to become a better strategic thinker

(47:59) The intricacies of implementing feedback

(51:53) Being a female leader in tech

(55:13) Advice for young women in tech

(56:07) Setting goals and aligning incentives

(01:01:40) Acknowledging hard truths

(01:05:46) Lessons from transitioning to Faire

(01:08:40) The importance of a good CPO/CEO relationship

(01:11:17) Vetting heads of product and maintaining customer focus

(01:12:40) How Ami went from intern to leading major products at Meta

(01:14:53) The one thing you should do to be successful in product

(01:17:25) Lightning round

Referenced:

• Faire: https://www.faire.com/

• Making Meta | Andrew “Boz” Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

•  Community Wisdom: AMA with Dan Hockenmaier + Facilitating a roadmap session, structuring product teams, navigating an acquisition, companies not needing PMs anymore, and much more: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

• Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge): https://www.lennysnewsletter.com/p/developing-a-growth-model-marketplace

• Dan Hockenmaier’s website: https://www.danhock.com/

• On Reviews: https://boz.com/articles/reviews

• Finding a global optimum always feels like a hill climb: https://www.linkedin.com/posts/amvora_finding-a-global-optimum-always-feels-like-activity-7074776143882588161-jhyy/

• Dolores Park: https://sfrecpark.org/892/Mission-Dolores-Park

• Rob Goldman on LinkedIn: https://www.linkedin.com/in/robgoldman/

• Execution eats strategy for breakfast, but execution without strategy leads to burnout: https://rationalpm.substack.com/p/execution-eats-strategy-for-breakfast

• The goal of a “strategy” is to change our own team’s behavior: https://amivora.substack.com/p/the-goal-of-a-strategy-is-to-change

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Path to Power course outline: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

• Max Rhodes on LinkedIn: https://www.linkedin.com/in/max-rhodes/

• Coupa Coffee: https://www.coupacafe.com/

• Brandee Barker on LinkedIn: https://www.linkedin.com/in/brandeedbarker/

Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person: https://www.amazon.com/Year-Yes-Dance-Stand-Person/dp/1476777128 

• How to tell better stories | Matthew Dicks (Storyworthy): https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/

• A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office

30 Rock on Peacock: https://www.peacocktv.com/watch-online/tv/30-rock/6240863759978157112

• Dall-E-2: https://openai.com/index/dall-e-2/

• ChatGPT: https://chatgpt.com

• Fellow kettles: https://fellowproducts.com/products/stagg-ekg-electric-pour-over-kettle

• TikTok’s “Roman Empire” Meme, Explained: https://www.forbes.com/sites/danidiplacido/2023/09/21/tiktoks-roman-empire-meme-explained/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Ami Vora is the Chief Product Officer of Faire, which connects independent retailers and brands around the world. Before Faire, Ami spent over 15 years at Meta, including as VP of Product and Design for WhatsApp (2B+ users), VP of Product for Facebook’s ads system (now $130B of annual revenue), and director at Instagram. She began her career working on developer tools at Microsoft. In our conversation, we discuss:

• Why execution eats strategy for breakfast

• Using metaphor to rally teams around one shared goal

• How to build cross-functional relationships

• “Dinosaur brain,” “Toddler soccer,” and the “hill climbing” metaphors

• A tactic for handling disagreement

• Tips for working well with product-minded founders as a product leader

• The story of Ami’s incredible 15-year journey from temp to VP at Meta

• Much more

Brought to you by:

Sidebar—Accelerate your career by surrounding yourself with extraordinary peers.

Anvil—The fastest way to build software for documents.

User Testing—Human understanding. Human experiences.

Find the transcript at: https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

Where to find Ami Vora:

• LinkedIn: https://www.linkedin.com/in/amvora/

• Substack: https://amivora.substack.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Ami’s background

(02:00) The myth of perfection in success

(07:55) Emotionally connecting with the job

(09:55) Embracing curiosity in moments of challenge

(13:16) Thinking in feedback loops

(17:17) The “dinosaur brain” metaphor in product reviews

(20:20) Strategies for conducting effective product reviews

(26:33) Using metaphors and imagery to communicate your vision

(29:35) The power of having a shared narrative

(31:55) WhatsApp: an example of metaphor in action

(34:44) Emulating people that inspire you

(36:19) WhatsApp video calling

(37:35) Why execution is greater than strategy

(41:36) Time allotment for strategy vs. execution

(45:10) How to become a better strategic thinker

(47:59) The intricacies of implementing feedback

(51:53) Being a female leader in tech

(55:13) Advice for young women in tech

(56:07) Setting goals and aligning incentives

(01:01:40) Acknowledging hard truths

(01:05:46) Lessons from transitioning to Faire

(01:08:40) The importance of a good CPO/CEO relationship

(01:11:17) Vetting heads of product and maintaining customer focus

(01:12:40) How Ami went from intern to leading major products at Meta

(01:14:53) The one thing you should do to be successful in product

(01:17:25) Lightning round

Referenced:

• Faire: https://www.faire.com/

• Making Meta | Andrew “Boz” Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

•  Community Wisdom: AMA with Dan Hockenmaier + Facilitating a roadmap session, structuring product teams, navigating an acquisition, companies not needing PMs anymore, and much more: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

• Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge): https://www.lennysnewsletter.com/p/developing-a-growth-model-marketplace

• Dan Hockenmaier’s website: https://www.danhock.com/

• On Reviews: https://boz.com/articles/reviews

• Finding a global optimum always feels like a hill climb: https://www.linkedin.com/posts/amvora_finding-a-global-optimum-always-feels-like-activity-7074776143882588161-jhyy/

• Dolores Park: https://sfrecpark.org/892/Mission-Dolores-Park

• Rob Goldman on LinkedIn: https://www.linkedin.com/in/robgoldman/

• Execution eats strategy for breakfast, but execution without strategy leads to burnout: https://rationalpm.substack.com/p/execution-eats-strategy-for-breakfast

• The goal of a “strategy” is to change our own team’s behavior: https://amivora.substack.com/p/the-goal-of-a-strategy-is-to-change

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Path to Power course outline: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

• Max Rhodes on LinkedIn: https://www.linkedin.com/in/max-rhodes/

• Coupa Coffee: https://www.coupacafe.com/

• Brandee Barker on LinkedIn: https://www.linkedin.com/in/brandeedbarker/

Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person: https://www.amazon.com/Year-Yes-Dance-Stand-Person/dp/1476777128 

• How to tell better stories | Matthew Dicks (Storyworthy): https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/

• A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office

30 Rock on Peacock: https://www.peacocktv.com/watch-online/tv/30-rock/6240863759978157112

• Dall-E-2: https://openai.com/index/dall-e-2/

• ChatGPT: https://chatgpt.com

• Fellow kettles: https://fellowproducts.com/products/stagg-ekg-electric-pour-over-kettle

• TikTok’s “Roman Empire” Meme, Explained: https://www.forbes.com/sites/danidiplacido/2023/09/21/tiktoks-roman-empire-meme-explained/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tanguy Crusson is the product lead for Jira Product Discovery at Atlassian. In his more than 10 years at the company, he has been instrumental in taking several new products from zero to one, including HipChat, Statuspage, and Jira Product Discovery. In this episode, we dive deep into the struggles of innovating and building new products inside a large company. Tanguy shares candid stories about what worked, what didn’t, and his many hard-won lessons learned about how to successfully build 0 to 1. We cover:

• Why large companies with so many advantages still fail at creating new products

• Lessons learned from building HipChat

• How to avoid common pitfalls like competitive myopia and premature scaling

• Lessons learned from the acquisition and integration of Statuspage

• Insights from the success of Jira Product Discovery

• Tactics for protecting your “ugly babies”

• The power of “lighthouse users”

• The importance of having a “why now”

• Much more

Brought to you by:

Vanta—Automate compliance. Simplify security

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

Where to find Tanguy Crusson:

• X: https://x.com/tanguycrusson

• LinkedIn: https://www.linkedin.com/in/tanguy-crusson-99832a

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Tanguy’s background

(02:30) Tanguy’s journey at Atlassian

(07:03) The challenges of innovating in large companies

(10:42) Atlassian's high bar for excellence 

(12:58) The HipChat story: successes, failures, and lessons learned

(20:47) Lessons learned from building HipChat

(33:49) Statuspage: a journey of perseverance

(39:48) Acquisition challenges and lessons

(47:22) Strategic decisions: build, buy, or partner?

(48:17) Learning to articulate "why now"

(54:08) A quick summary of lessons in this episode

(55:40) The success and pain of launching Jira Product Discovery 

(58:10) Incubating new products: the Point A program

(01:00:13) Failure is the most likely outcome

(01:04:15) Atlassian's four-phase approach to launching new products

(01:09:20) Breaking rules without breaking trust

(01:16:16) Early success and team autonomy

(01:17:22) Innovating without disrupting existing customers

(01:23:17) The Lighthouse Users program

(01:30:00) Protecting and nurturing new ideas

(01:36:14) Balancing innovation with personal well-being

(01:38:17) A reminder to look after yourself

(01:42:06) Lightning round

Referenced:

• Atlassian: https://www.atlassian.com/

• HipChat: https://community.atlassian.com/t5/Hipchat/ct-p/hipchat

• Stride: https://community.atlassian.com/t5/Stride/ct-p/stride

• Statuspage: https://www.atlassian.com/software/statuspage

• Opsgenie: https://www.atlassian.com/software/opsgenie

• Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

• HipChat billboard: https://x.com/HubSpot/status/654696998126272512

• Announcing our new partnership with Slack: https://www.atlassian.com/blog/announcements/new-atlassian-slack-partnership

• Slack shows it’s worried about Microsoft Teams with a full-page newspaper ad: https://www.theverge.com/2016/11/2/13497766/slack-microsoft-teams-new-york-times-ad

• What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Jira: https://www.atlassian.com/software/jira

• Confluence: https://www.atlassian.com/software/confluence

• PagerDuty: https://www.pagerduty.com/

• New Relic: https://newrelic.com/

• BigPanda: https://www.bigpanda.io/

• Transparent Uptime: http://www.transparentuptime.com/

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Figma: https://www.figma.com/

• Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira): https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

• Noah Weiss on LinkedIn: https://www.linkedin.com/in/noahw/

• Tanguy’s LinkedIn post about “lighthouse users”: https://www.linkedin.com/posts/tanguy-crusson-99832a_lighthouse-users-one-of-the-pm-techniques-activity-7176654510801502210-hWNi/

• Pixar Chief: Protect Your ‘Ugly Babies’ (Your Unsightly Ideas): https://www.forbes.com/sites/andyboynton/2014/03/17/pixar-chief-protect-your-ugly-babies-your-unsightly-ideas/

• Atlas: https://www.atlassian.com/software/atlas

• Point A: https://www.atlassian.com/point-a

• Scott Farquhar on LinkedIn: https://www.linkedin.com/in/scottfarquhar

Who: A Method for Hiring: https://www.amazon.com/Who-Method-Hiring-HC-2008/dp/B004C79SRS/

Hakim’s Odyssey: Book 1: From Syria to Turkey: https://www.amazon.com/Hakims-Odyssey-Book-Syria-Turkey/dp/1637790007

Living with the Earth, Volume 1: Permaculture, Ecoculture: Inspired by Nature: https://www.amazon.com/Living-Earth-Gardeners-Permaculture-Ecoculture/dp/1856232603/

• INRIA: https://en.wikipedia.org/wiki/French_Institute_for_Research_in_Computer_Science_and_Automation

• How a Hydrofoil Works: https://web.mit.edu/2.972/www/reports/hydrofoil/hydrofoil.html

• What Is Kitefoil or Foilboarding?: https://www.whenitswindy.com/wp/?page_id=534

• Freediving: https://en.wikipedia.org/wiki/Freediving

• Tanguy’s freediving stats: https://www.aidainternational.org/Athletes/Profile-00000000-0000-0000-0000-000000000a45

• Perplexity: https://www.perplexity.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Tanguy Crusson is the product lead for Jira Product Discovery at Atlassian. In his more than 10 years at the company, he has been instrumental in taking several new products from zero to one, including HipChat, Statuspage, and Jira Product Discovery. In this episode, we dive deep into the struggles of innovating and building new products inside a large company. Tanguy shares candid stories about what worked, what didn’t, and his many hard-won lessons learned about how to successfully build 0 to 1. We cover:

• Why large companies with so many advantages still fail at creating new products

• Lessons learned from building HipChat

• How to avoid common pitfalls like competitive myopia and premature scaling

• Lessons learned from the acquisition and integration of Statuspage

• Insights from the success of Jira Product Discovery

• Tactics for protecting your “ugly babies”

• The power of “lighthouse users”

• The importance of having a “why now”

• Much more

Brought to you by:

Vanta—Automate compliance. Simplify security

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

Where to find Tanguy Crusson:

• X: https://x.com/tanguycrusson

• LinkedIn: https://www.linkedin.com/in/tanguy-crusson-99832a

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Tanguy’s background

(02:30) Tanguy’s journey at Atlassian

(07:03) The challenges of innovating in large companies

(10:42) Atlassian's high bar for excellence 

(12:58) The HipChat story: successes, failures, and lessons learned

(20:47) Lessons learned from building HipChat

(33:49) Statuspage: a journey of perseverance

(39:48) Acquisition challenges and lessons

(47:22) Strategic decisions: build, buy, or partner?

(48:17) Learning to articulate "why now"

(54:08) A quick summary of lessons in this episode

(55:40) The success and pain of launching Jira Product Discovery 

(58:10) Incubating new products: the Point A program

(01:00:13) Failure is the most likely outcome

(01:04:15) Atlassian's four-phase approach to launching new products

(01:09:20) Breaking rules without breaking trust

(01:16:16) Early success and team autonomy

(01:17:22) Innovating without disrupting existing customers

(01:23:17) The Lighthouse Users program

(01:30:00) Protecting and nurturing new ideas

(01:36:14) Balancing innovation with personal well-being

(01:38:17) A reminder to look after yourself

(01:42:06) Lightning round

Referenced:

• Atlassian: https://www.atlassian.com/

• HipChat: https://community.atlassian.com/t5/Hipchat/ct-p/hipchat

• Stride: https://community.atlassian.com/t5/Stride/ct-p/stride

• Statuspage: https://www.atlassian.com/software/statuspage

• Opsgenie: https://www.atlassian.com/software/opsgenie

• Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

• HipChat billboard: https://x.com/HubSpot/status/654696998126272512

• Announcing our new partnership with Slack: https://www.atlassian.com/blog/announcements/new-atlassian-slack-partnership

• Slack shows it’s worried about Microsoft Teams with a full-page newspaper ad: https://www.theverge.com/2016/11/2/13497766/slack-microsoft-teams-new-york-times-ad

• What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Jira: https://www.atlassian.com/software/jira

• Confluence: https://www.atlassian.com/software/confluence

• PagerDuty: https://www.pagerduty.com/

• New Relic: https://newrelic.com/

• BigPanda: https://www.bigpanda.io/

• Transparent Uptime: http://www.transparentuptime.com/

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Figma: https://www.figma.com/

• Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira): https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

• Noah Weiss on LinkedIn: https://www.linkedin.com/in/noahw/

• Tanguy’s LinkedIn post about “lighthouse users”: https://www.linkedin.com/posts/tanguy-crusson-99832a_lighthouse-users-one-of-the-pm-techniques-activity-7176654510801502210-hWNi/

• Pixar Chief: Protect Your ‘Ugly Babies’ (Your Unsightly Ideas): https://www.forbes.com/sites/andyboynton/2014/03/17/pixar-chief-protect-your-ugly-babies-your-unsightly-ideas/

• Atlas: https://www.atlassian.com/software/atlas

• Point A: https://www.atlassian.com/point-a

• Scott Farquhar on LinkedIn: https://www.linkedin.com/in/scottfarquhar

Who: A Method for Hiring: https://www.amazon.com/Who-Method-Hiring-HC-2008/dp/B004C79SRS/

Hakim’s Odyssey: Book 1: From Syria to Turkey: https://www.amazon.com/Hakims-Odyssey-Book-Syria-Turkey/dp/1637790007

Living with the Earth, Volume 1: Permaculture, Ecoculture: Inspired by Nature: https://www.amazon.com/Living-Earth-Gardeners-Permaculture-Ecoculture/dp/1856232603/

• INRIA: https://en.wikipedia.org/wiki/French_Institute_for_Research_in_Computer_Science_and_Automation

• How a Hydrofoil Works: https://web.mit.edu/2.972/www/reports/hydrofoil/hydrofoil.html

• What Is Kitefoil or Foilboarding?: https://www.whenitswindy.com/wp/?page_id=534

• Freediving: https://en.wikipedia.org/wiki/Freediving

• Tanguy’s freediving stats: https://www.aidainternational.org/Athletes/Profile-00000000-0000-0000-0000-000000000a45

• Perplexity: https://www.perplexity.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jeffrey Pfeffer teaches the single most popular (and somewhat controversial) class at Stanford’s Graduate School of Business: The Paths to Power. He’s also the author of 16 books, including 7 Rules of Power: Surprising—But True—Advice on How to Get Things Done and Advance Your Career. He has taught at Harvard, the London Business School, and IESE and has written for publications like Fortune and the Washington Post. Recognized by the Academy of Management and listed in the Thinkers50 Hall of Fame, Jeffrey also serves on several corporate and nonprofit boards, bringing his expertise to global audiences through seminars and executive education. In our conversation, we discuss:

• Jeffrey’s seven rules of power

• How individuals can acquire and use power in business

• Networking, and how to do it effectively

• How to build a non-cringe personal brand

• How to increase your influence to amplify your impact

• Examples and stories of people building power

• Tradeoffs and challenges that come with power

Brought to you by:

Uizard—AI-powered prototyping for visionary product leaders

Webflow—The web experience platform

Heap—Cross-platform product analytics that converts, engages, and retains customers

Find the transcript at: https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

Where to find Jeffrey Pfeffer:

• X: https://x.com/JeffreyPfeffer

• LinkedIn: https://www.linkedin.com/in/jeffrey-pfeffer-57a01b6/

• Website: https://jeffreypfeffer.com/

• Podcast: https://jeffreypfeffer.com/pfeffer-on-power/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jeffrey’s background 

(02:54) Understanding discomfort with power

(04:56) Power skills for underrepresented groups

(07:51) The popularity and challenges of Jeffrey’s class at Stanford

(12:21) The seven rules of power

(13:03) Success stories from his course

(15:43) Building a personal brand

(21:11) Getting out of your own way

(26:04) Breaking the rules to gain power

(30:34) Networking relentlessly

(40:10) Why Jeffrey says to “pursue weak ties”

(42:00) Using your power to build more power

(44:34) The importance of appearance and body language

(47:15) Mastering the art of presentation

(55:12) Examples of homework assignments that Jeffrey gives students

(59:11) People will forget how you acquired power

(01:03:58) More good people need to have power

(01:10:49) The price of power and autonomy

(01:17:13) A homework assignment for you

Referenced:

• Gerald Ferris on LinkedIn: https://www.linkedin.com/in/gerald-r-ferris-5816b1b5/

• Political Skill at Work: https://tarjomefa.com/wp-content/uploads/2015/10/4173-engilish.pdf

• Laura Esserman, MD: https://cancer.ucsf.edu/people/esserman.laura

• Taylor Swift’s website: https://www.taylorswift.com/

• Matthew 7: https://www.biblegateway.com/passage/?search=Matthew%207&version=NIV

• Mother Teresa quote: https://www.goodreads.com/quotes/2887-if-you-judge-people-you-have-no-time-to-love

• Paths to Power course description: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/

The Knowing-Doing Gap: https://jeffreypfeffer.com/books/the-knowing-doing-gap/

• Derek Kan on LinkedIn: https://www.linkedin.com/in/derekkan/

• Mitt Romney on X: https://x.com/mittromney

• Elaine Chao’s website: https://www.elainechao.com/

• Tony Hsieh: https://en.wikipedia.org/wiki/Tony_Hsieh

• Zappos: https://www.zappos.com/

• How I Did It: Zappos’s CEO on Going to Extremes for Customers: https://hbr.org/2010/07/how-i-did-it-zapposs-ceo-on-going-to-extremes-for-customers

• McKinsey & Company: https://www.mckinsey.com/

• Bain & Company: https://www.bain.com/

• BCG: https://www.bcg.com/

• Keith Ferrazzi’s website: https://www.keithferrazzi.com/

• Deloitte: https://www2.deloitte.com/

• Tristan Walker: https://www.linkedin.com/in/tristanwalker/

• Foursquare: https://foursquare.com/

• Laura Chau on LinkedIn: https://www.linkedin.com/in/laura-chau/

• Canaan Partners: https://www.canaan.com/

• Andreessen Horowitz: https://a16z.com/

• Sequoia Capital: https://www.sequoiacap.com/

• Greylock: https://greylock.com/

The Women Who Venture (WoVen) Podcast: https://www.canaan.com/woven/podcasts

• Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome

• Gary Loveman and Harrah’s Entertainment: https://www.gsb.stanford.edu/faculty-research/case-studies/gary-loveman-harrahs-entertainment

• “If you need help, just ask”: Underestimating compliance with direct requests for help: https://www.gsb.stanford.edu/faculty-research/publications/if-you-need-help-just-ask-underestimating-compliance-direct-requests

• Life story of Kathleen Frances Fowler: https://www.forevermissed.com/kathleenfowler/lifestory

• Jason Calacanis on LinkedIn: https://www.linkedin.com/in/jasoncalacanis/

• Jason Calacanis: A Case Study in Creating Resources: https://www.gsb.stanford.edu/faculty-research/case-studies/jason-calacanis-case-study-creating-resources

You’re Invited: The Art and Science of Connection, Trust, and Belonging: https://www.amazon.com/Youre-Invited-Science-Cultivating-Influence/dp/0063030977

• View from the Top: https://www.gsb.stanford.edu/experience/learning/guest-speakers/view-top

• Omid Kordestani on LinkedIn: https://www.linkedin.com/in/omid-kordestani-46515151/

• Netscape: https://en.wikipedia.org/wiki/Netscape

•  Esther Wojcicki on LinkedIn:  https://www.linkedin.com/in/estherwojcicki/

• Leanne Williams: https://med.stanford.edu/profiles/leanne-williams

Precision Psychiatry: Using Neuroscience Insights to Inform Personally Tailored, Measurement-Based Care: https://www.amazon.com/Precision-Psychiatry-Neuroscience-Personally-Measurement-Based/dp/1615371583

• Mark Granovetter on LinkedIn: https://www.linkedin.com/in/mark-granovetter-8161704/

• The Strength of Weak Ties: https://snap.stanford.edu/class/cs224w-readings/granovetter73weakties.pdf

Getting a Jobhttps://www.amazon.com/Getting-Job-Study-Contacts-Careers/dp/0226305813

Acting with Power: https://www.amazon.com/Acting-Power-More-Powerful-Believe/dp/110190397X

• Articles by Herminia Ibarra: https://herminiaibarra.com/articles/

Kingdom of the Planet of the Ape: https://www.imdb.com/title/tt11389872/

• Jim Collins’s website: https://www.jimcollins.com/

• Dana Carney on LinkedIn: https://www.linkedin.com/in/danarosecarney/

• Baba Shiv: https://www.gsb.stanford.edu/faculty-research/faculty/baba-shiv

• Tony Hayward: https://en.wikipedia.org/wiki/Tony_Hayward

• Lloyd Blankfein: https://en.wikipedia.org/wiki/Lloyd_Blankfein

• Regis McKenna: https://en.wikipedia.org/wiki/Regis_McKenna

• Jack Valenti: https://en.wikipedia.org/wiki/Jack_Valenti

• Salman Rushdie quote: https://www.pinterest.com/pin/434175220328596286/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• Carole Robin’s 15% rule: https://pen-name.notion.site/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

• Karlie Kloss on Instagram: https://www.instagram.com/karliekloss

• Lindsey Graham’s website: https://www.lindseygraham.com/

• Was Microsoft’s Empire Built on Stolen Code? We May Never Know: https://www.wired.com/2012/08/ms-dos-examined-for-thef/

• Who’s who of Jeffrey Epstein’s powerful friends, associates and possible co-conspirators: https://www.cnn.com/2019/08/12/us/jeffrey-epstein-associates-possible-accomplices/index.html

• Why Did Martha Stewart Go to Prison? A Look Back at Her 2004 Fraud Case: https://people.com/martha-stewart-fraud-case-prison-sentence-look-back-8550277

• Dianne Feinstein: https://www.congress.gov/member/dianne-feinstein/F000062

• Richard Blum: https://en.wikipedia.org/wiki/Richard_C._Blum

• Athena Care Network: https://www.athenacarenetwork.org

• James G. March: https://en.wikipedia.org/wiki/James_G._March

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• Trump Organization fined $1.6 million for tax fraud: https://apnews.com/article/politics-legal-proceedings-new-york-city-donald-trump-manhattan-e2f1d01525dafb64be8738c8b4f32085

• Rudy Giuliani: https://en.wikipedia.org/wiki/Rudy_Giuliani

• Harvard president resigns amid claims of plagiarism and antisemitism backlash: https://www.theguardian.com/education/2024/jan/02/harvard-president-claudine-gay-resigns

• Stanford president resigns after fallout from falsified data in his research: https://www.npr.org/2023/07/19/1188828810/stanford-university-president-resigns

• Rudy Crew: https://en.wikipedia.org/wiki/Rudy_Crew

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jeffrey Pfeffer teaches the single most popular (and somewhat controversial) class at Stanford’s Graduate School of Business: The Paths to Power. He’s also the author of 16 books, including 7 Rules of Power: Surprising—But True—Advice on How to Get Things Done and Advance Your Career. He has taught at Harvard, the London Business School, and IESE and has written for publications like Fortune and the Washington Post. Recognized by the Academy of Management and listed in the Thinkers50 Hall of Fame, Jeffrey also serves on several corporate and nonprofit boards, bringing his expertise to global audiences through seminars and executive education. In our conversation, we discuss:

• Jeffrey’s seven rules of power

• How individuals can acquire and use power in business

• Networking, and how to do it effectively

• How to build a non-cringe personal brand

• How to increase your influence to amplify your impact

• Examples and stories of people building power

• Tradeoffs and challenges that come with power

Brought to you by:

Uizard—AI-powered prototyping for visionary product leaders

Webflow—The web experience platform

Heap—Cross-platform product analytics that converts, engages, and retains customers

Find the transcript at: https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

Where to find Jeffrey Pfeffer:

• X: https://x.com/JeffreyPfeffer

• LinkedIn: https://www.linkedin.com/in/jeffrey-pfeffer-57a01b6/

• Website: https://jeffreypfeffer.com/

• Podcast: https://jeffreypfeffer.com/pfeffer-on-power/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jeffrey’s background 

(02:54) Understanding discomfort with power

(04:56) Power skills for underrepresented groups

(07:51) The popularity and challenges of Jeffrey’s class at Stanford

(12:21) The seven rules of power

(13:03) Success stories from his course

(15:43) Building a personal brand

(21:11) Getting out of your own way

(26:04) Breaking the rules to gain power

(30:34) Networking relentlessly

(40:10) Why Jeffrey says to “pursue weak ties”

(42:00) Using your power to build more power

(44:34) The importance of appearance and body language

(47:15) Mastering the art of presentation

(55:12) Examples of homework assignments that Jeffrey gives students

(59:11) People will forget how you acquired power

(01:03:58) More good people need to have power

(01:10:49) The price of power and autonomy

(01:17:13) A homework assignment for you

Referenced:

• Gerald Ferris on LinkedIn: https://www.linkedin.com/in/gerald-r-ferris-5816b1b5/

• Political Skill at Work: https://tarjomefa.com/wp-content/uploads/2015/10/4173-engilish.pdf

• Laura Esserman, MD: https://cancer.ucsf.edu/people/esserman.laura

• Taylor Swift’s website: https://www.taylorswift.com/

• Matthew 7: https://www.biblegateway.com/passage/?search=Matthew%207&version=NIV

• Mother Teresa quote: https://www.goodreads.com/quotes/2887-if-you-judge-people-you-have-no-time-to-love

• Paths to Power course description: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf

7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/

The Knowing-Doing Gap: https://jeffreypfeffer.com/books/the-knowing-doing-gap/

• Derek Kan on LinkedIn: https://www.linkedin.com/in/derekkan/

• Mitt Romney on X: https://x.com/mittromney

• Elaine Chao’s website: https://www.elainechao.com/

• Tony Hsieh: https://en.wikipedia.org/wiki/Tony_Hsieh

• Zappos: https://www.zappos.com/

• How I Did It: Zappos’s CEO on Going to Extremes for Customers: https://hbr.org/2010/07/how-i-did-it-zapposs-ceo-on-going-to-extremes-for-customers

• McKinsey & Company: https://www.mckinsey.com/

• Bain & Company: https://www.bain.com/

• BCG: https://www.bcg.com/

• Keith Ferrazzi’s website: https://www.keithferrazzi.com/

• Deloitte: https://www2.deloitte.com/

• Tristan Walker: https://www.linkedin.com/in/tristanwalker/

• Foursquare: https://foursquare.com/

• Laura Chau on LinkedIn: https://www.linkedin.com/in/laura-chau/

• Canaan Partners: https://www.canaan.com/

• Andreessen Horowitz: https://a16z.com/

• Sequoia Capital: https://www.sequoiacap.com/

• Greylock: https://greylock.com/

The Women Who Venture (WoVen) Podcast: https://www.canaan.com/woven/podcasts

• Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome

• Gary Loveman and Harrah’s Entertainment: https://www.gsb.stanford.edu/faculty-research/case-studies/gary-loveman-harrahs-entertainment

• “If you need help, just ask”: Underestimating compliance with direct requests for help: https://www.gsb.stanford.edu/faculty-research/publications/if-you-need-help-just-ask-underestimating-compliance-direct-requests

• Life story of Kathleen Frances Fowler: https://www.forevermissed.com/kathleenfowler/lifestory

• Jason Calacanis on LinkedIn: https://www.linkedin.com/in/jasoncalacanis/

• Jason Calacanis: A Case Study in Creating Resources: https://www.gsb.stanford.edu/faculty-research/case-studies/jason-calacanis-case-study-creating-resources

You’re Invited: The Art and Science of Connection, Trust, and Belonging: https://www.amazon.com/Youre-Invited-Science-Cultivating-Influence/dp/0063030977

• View from the Top: https://www.gsb.stanford.edu/experience/learning/guest-speakers/view-top

• Omid Kordestani on LinkedIn: https://www.linkedin.com/in/omid-kordestani-46515151/

• Netscape: https://en.wikipedia.org/wiki/Netscape

•  Esther Wojcicki on LinkedIn:  https://www.linkedin.com/in/estherwojcicki/

• Leanne Williams: https://med.stanford.edu/profiles/leanne-williams

Precision Psychiatry: Using Neuroscience Insights to Inform Personally Tailored, Measurement-Based Care: https://www.amazon.com/Precision-Psychiatry-Neuroscience-Personally-Measurement-Based/dp/1615371583

• Mark Granovetter on LinkedIn: https://www.linkedin.com/in/mark-granovetter-8161704/

• The Strength of Weak Ties: https://snap.stanford.edu/class/cs224w-readings/granovetter73weakties.pdf

Getting a Jobhttps://www.amazon.com/Getting-Job-Study-Contacts-Careers/dp/0226305813

Acting with Power: https://www.amazon.com/Acting-Power-More-Powerful-Believe/dp/110190397X

• Articles by Herminia Ibarra: https://herminiaibarra.com/articles/

Kingdom of the Planet of the Ape: https://www.imdb.com/title/tt11389872/

• Jim Collins’s website: https://www.jimcollins.com/

• Dana Carney on LinkedIn: https://www.linkedin.com/in/danarosecarney/

• Baba Shiv: https://www.gsb.stanford.edu/faculty-research/faculty/baba-shiv

• Tony Hayward: https://en.wikipedia.org/wiki/Tony_Hayward

• Lloyd Blankfein: https://en.wikipedia.org/wiki/Lloyd_Blankfein

• Regis McKenna: https://en.wikipedia.org/wiki/Regis_McKenna

• Jack Valenti: https://en.wikipedia.org/wiki/Jack_Valenti

• Salman Rushdie quote: https://www.pinterest.com/pin/434175220328596286/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• Carole Robin’s 15% rule: https://pen-name.notion.site/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

• Karlie Kloss on Instagram: https://www.instagram.com/karliekloss

• Lindsey Graham’s website: https://www.lindseygraham.com/

• Was Microsoft’s Empire Built on Stolen Code? We May Never Know: https://www.wired.com/2012/08/ms-dos-examined-for-thef/

• Who’s who of Jeffrey Epstein’s powerful friends, associates and possible co-conspirators: https://www.cnn.com/2019/08/12/us/jeffrey-epstein-associates-possible-accomplices/index.html

• Why Did Martha Stewart Go to Prison? A Look Back at Her 2004 Fraud Case: https://people.com/martha-stewart-fraud-case-prison-sentence-look-back-8550277

• Dianne Feinstein: https://www.congress.gov/member/dianne-feinstein/F000062

• Richard Blum: https://en.wikipedia.org/wiki/Richard_C._Blum

• Athena Care Network: https://www.athenacarenetwork.org

• James G. March: https://en.wikipedia.org/wiki/James_G._March

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• Trump Organization fined $1.6 million for tax fraud: https://apnews.com/article/politics-legal-proceedings-new-york-city-donald-trump-manhattan-e2f1d01525dafb64be8738c8b4f32085

• Rudy Giuliani: https://en.wikipedia.org/wiki/Rudy_Giuliani

• Harvard president resigns amid claims of plagiarism and antisemitism backlash: https://www.theguardian.com/education/2024/jan/02/harvard-president-claudine-gay-resigns

• Stanford president resigns after fallout from falsified data in his research: https://www.npr.org/2023/07/19/1188828810/stanford-university-president-resigns

• Rudy Crew: https://en.wikipedia.org/wiki/Rudy_Crew

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Uri Levine is the co-founder of Waze, the world’s largest community-based traffic and navigation app, acquired by Google for over $1 billion. He’s also founded nine other companies, been on the board of 20 companies, and advised more than 50 companies. He’s most recently the author of Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs, hailed by Steve Wozniak as the “Bible for entrepreneurs.” Uri is dedicated to creating impactful startups that solve real-world problems and has seen everything from failure to moderate success to big success. In our conversation, we dig into:

• Why falling in love with the problem is key to startup success

• The phases of the startup journey and how to navigate them

• Why firing is more important than hiring

• How Waze iterated to achieve product-market fit

• Tactics for telling a compelling story when fundraising

• Much more

Brought to you by:

Vanta—Automate compliance. Simplify security

Mercury—The powerful and intuitive way for ambitious companies to bank

LinkedIn Ads—Reach professionals and drive results for your business

Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-uri-levine

Where to find Uri Levine:

• X: https://twitter.com/urilevine1

• LinkedIn: https://www.linkedin.com/in/uri-levine

• Website: https://urilevine.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Uri’s background

(02:50) Falling in love with the problem

(09:03) Signs this is a big enough problem

(10:54) The importance of passion

(12:06) A pivot example

(14:01) Where to find startup ideas

(21:57) Finding product-market fit at Waze

(29:45) The different phases of a startup journey

(36:47) What investors don’t want to hear

(39:53) Fundraising tips

(48:02) How to make your presentations stronger

(50:32) A wild fundraising story

(53:46) Firing and hiring

(59:50) The 30-day test

(01:04:12) Understanding users

(01:12:10) Talking to the right users

(01:15:36) Lightning round

Referenced:

Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987

• Waze: https://www.waze.com/

• Ben Horowitz on LinkedIn: https://www.linkedin.com/in/behorowitz/

• Ben Horowitz quote: https://quotefancy.com/quote/1635284/Ben-Horowitz-As-a-startup-CEO-I-slept-like-a-baby-I-woke-up-every-2-hours-and-cried

• Michael Jordan quote: https://www.forbes.com/quotes/11194/#:~:text=I've%20lost%20almost%20300,that%20is%20why%20I%20succeed.

• Steph Curry: https://en.wikipedia.org/wiki/Stephen_Curry

• How Airbnb Used Word of Mouth to Change the Travel Industry Forever: https://truested.com/story/airbnb

• Space Mountain: https://en.wikipedia.org/wiki/Space_Mountain_(Disneyland)

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Uri’s post about the conference in Guatemala with Steve Wozniak: https://www.linkedin.com/posts/uri-levine_jewishnewyear-speakers-book-activity-6980089544079486976-0ADa/

• Leonardo da Vinci quote: https://www.goodreads.com/quotes/9010638-simplicity-is-the-ultimate-sophistication-when-once-you-have-tasted

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

• Nana Korobi Ya Oki: https://ikigaitribe.com/vlog/nana-korobi-ya-oki/

That Will Never Work: The Birth of Netflix and the Amazing Life of an Idea: https://www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530204

Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

• 8 Great Chess Apps for Beginners and Grand Masters: https://www.wired.com/story/best-chess-apps/

• Pontera: https://pontera.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Uri Levine is the co-founder of Waze, the world’s largest community-based traffic and navigation app, acquired by Google for over $1 billion. He’s also founded nine other companies, been on the board of 20 companies, and advised more than 50 companies. He’s most recently the author of Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs, hailed by Steve Wozniak as the “Bible for entrepreneurs.” Uri is dedicated to creating impactful startups that solve real-world problems and has seen everything from failure to moderate success to big success. In our conversation, we dig into:

• Why falling in love with the problem is key to startup success

• The phases of the startup journey and how to navigate them

• Why firing is more important than hiring

• How Waze iterated to achieve product-market fit

• Tactics for telling a compelling story when fundraising

• Much more

Brought to you by:

Vanta—Automate compliance. Simplify security

Mercury—The powerful and intuitive way for ambitious companies to bank

LinkedIn Ads—Reach professionals and drive results for your business

Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-uri-levine

Where to find Uri Levine:

• X: https://twitter.com/urilevine1

• LinkedIn: https://www.linkedin.com/in/uri-levine

• Website: https://urilevine.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Uri’s background

(02:50) Falling in love with the problem

(09:03) Signs this is a big enough problem

(10:54) The importance of passion

(12:06) A pivot example

(14:01) Where to find startup ideas

(21:57) Finding product-market fit at Waze

(29:45) The different phases of a startup journey

(36:47) What investors don’t want to hear

(39:53) Fundraising tips

(48:02) How to make your presentations stronger

(50:32) A wild fundraising story

(53:46) Firing and hiring

(59:50) The 30-day test

(01:04:12) Understanding users

(01:12:10) Talking to the right users

(01:15:36) Lightning round

Referenced:

Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987

• Waze: https://www.waze.com/

• Ben Horowitz on LinkedIn: https://www.linkedin.com/in/behorowitz/

• Ben Horowitz quote: https://quotefancy.com/quote/1635284/Ben-Horowitz-As-a-startup-CEO-I-slept-like-a-baby-I-woke-up-every-2-hours-and-cried

• Michael Jordan quote: https://www.forbes.com/quotes/11194/#:~:text=I've%20lost%20almost%20300,that%20is%20why%20I%20succeed.

• Steph Curry: https://en.wikipedia.org/wiki/Stephen_Curry

• How Airbnb Used Word of Mouth to Change the Travel Industry Forever: https://truested.com/story/airbnb

• Space Mountain: https://en.wikipedia.org/wiki/Space_Mountain_(Disneyland)

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Uri’s post about the conference in Guatemala with Steve Wozniak: https://www.linkedin.com/posts/uri-levine_jewishnewyear-speakers-book-activity-6980089544079486976-0ADa/

• Leonardo da Vinci quote: https://www.goodreads.com/quotes/9010638-simplicity-is-the-ultimate-sophistication-when-once-you-have-tasted

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

• Nana Korobi Ya Oki: https://ikigaitribe.com/vlog/nana-korobi-ya-oki/

That Will Never Work: The Birth of Netflix and the Amazing Life of an Idea: https://www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530204

Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

• 8 Great Chess Apps for Beginners and Grand Masters: https://www.wired.com/story/best-chess-apps/

• Pontera: https://pontera.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Cameron Adams is the co-founder and chief product officer of Canva. Canva is one of the world’s most valuable private software companies, used by 95% of Fortune 500 companies. Since its launch in 2013, Canva has grown to over 150 million monthly users in more than 190 countries, generating $2.3 billion in annual revenue. Prior to Canva, Cameron ran a design consultancy, worked at Google on Google Wave, and founded the email startup Fluent. He is also an author of five web design books and a regular speaker at global conferences. In our conversation, we discuss:

• Why they spent a year building their minimum viable product (MVP) before launch

• Why Canva has no managers, and their unique approach to coaching and performance reviews

• Why they encourage employees to “give away their Legos”

• Insights into Canva’s SEO growth strategy

• Their three-pillar framework for integrating AI into their product

• Stories from the early days

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Attio—The powerful, flexible CRM for fast-growing startups

Vanta—Automate compliance. Simplify security.

Find the transcript at: https://www.lennysnewsletter.com/p/inside-canva-with-cameron-adams

Where to find Cameron Adams:

• X: https://twitter.com/themaninblue

• LinkedIn: https://www.linkedin.com/in/themaninblue

• Website: https://themaninblue.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Cameron’s background

(02:00) Reflecting on the success of Canva

(04:50) Reflecting on hard times

(10:01) Canva’s product-obsessed culture

(12:02) Why they prioritize internal promotions and hires

(13:56) What makes Canva unique

(16:31) The concept of giving away your Legos

(21:44) Why Canva has no managers

(24:29) Product management at Canva

(27:56) Reflections on working with a married couple

(30:37) Why they spent a year building their MVP before launch

(33:49) Advice for building an MVP

(41:23) Canva’s onboarding transformation

(44:25) Canva’s SEO strategy

(50:37) The success of Canva’s freemium strategy

(54:24) Integrating AI into Canva’s product

(01:01:50) Where to find Cameron

Referenced:

• Canva: https://www.canva.com/

• Melanie Perkins on LinkedIn: https://www.linkedin.com/in/melanieperkins

• Cliff Obrecht on LinkedIn: https://www.linkedin.com/in/cliff-obrecht-79ba9920

• Jennie Rogerson, Head of People, LinkedIn post about “season opener” events: https://www.linkedin.com/posts/jennierogerson_season-opener-is-one-of-my-favourite-events-activity-7006815614556135424-73bD/

Game of Thrones on HBO: https://www.hbo.com/game-of-thrones

• Woodstock: https://en.wikipedia.org/wiki/Woodstock

• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/

• Minimum viable product (MVP): https://www.productboard.com/glossary/minimum-viable-product-mvp

• Canva’s SEO Strategy Is Elite: https://thegrowthplaybook.substack.com/p/canvas-seo-strategy-is-elite

• The SEO Strategy That Led Canva to a $40 Billion Valuation: https://www.youtube.com/watch?v=INyGKt6LAqM

• Andrianes Pinantoan on LinkedIn: https://www.linkedin.com/in/andrianes/

• Canva Create: https://www.canva.com/canva-create/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Cameron Adams is the co-founder and chief product officer of Canva. Canva is one of the world’s most valuable private software companies, used by 95% of Fortune 500 companies. Since its launch in 2013, Canva has grown to over 150 million monthly users in more than 190 countries, generating $2.3 billion in annual revenue. Prior to Canva, Cameron ran a design consultancy, worked at Google on Google Wave, and founded the email startup Fluent. He is also an author of five web design books and a regular speaker at global conferences. In our conversation, we discuss:

• Why they spent a year building their minimum viable product (MVP) before launch

• Why Canva has no managers, and their unique approach to coaching and performance reviews

• Why they encourage employees to “give away their Legos”

• Insights into Canva’s SEO growth strategy

• Their three-pillar framework for integrating AI into their product

• Stories from the early days

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Attio—The powerful, flexible CRM for fast-growing startups

Vanta—Automate compliance. Simplify security.

Find the transcript at: https://www.lennysnewsletter.com/p/inside-canva-with-cameron-adams

Where to find Cameron Adams:

• X: https://twitter.com/themaninblue

• LinkedIn: https://www.linkedin.com/in/themaninblue

• Website: https://themaninblue.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Cameron’s background

(02:00) Reflecting on the success of Canva

(04:50) Reflecting on hard times

(10:01) Canva’s product-obsessed culture

(12:02) Why they prioritize internal promotions and hires

(13:56) What makes Canva unique

(16:31) The concept of giving away your Legos

(21:44) Why Canva has no managers

(24:29) Product management at Canva

(27:56) Reflections on working with a married couple

(30:37) Why they spent a year building their MVP before launch

(33:49) Advice for building an MVP

(41:23) Canva’s onboarding transformation

(44:25) Canva’s SEO strategy

(50:37) The success of Canva’s freemium strategy

(54:24) Integrating AI into Canva’s product

(01:01:50) Where to find Cameron

Referenced:

• Canva: https://www.canva.com/

• Melanie Perkins on LinkedIn: https://www.linkedin.com/in/melanieperkins

• Cliff Obrecht on LinkedIn: https://www.linkedin.com/in/cliff-obrecht-79ba9920

• Jennie Rogerson, Head of People, LinkedIn post about “season opener” events: https://www.linkedin.com/posts/jennierogerson_season-opener-is-one-of-my-favourite-events-activity-7006815614556135424-73bD/

Game of Thrones on HBO: https://www.hbo.com/game-of-thrones

• Woodstock: https://en.wikipedia.org/wiki/Woodstock

• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/

• Minimum viable product (MVP): https://www.productboard.com/glossary/minimum-viable-product-mvp

• Canva’s SEO Strategy Is Elite: https://thegrowthplaybook.substack.com/p/canvas-seo-strategy-is-elite

• The SEO Strategy That Led Canva to a $40 Billion Valuation: https://www.youtube.com/watch?v=INyGKt6LAqM

• Andrianes Pinantoan on LinkedIn: https://www.linkedin.com/in/andrianes/

• Canva Create: https://www.canva.com/canva-create/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss:

• Why 40% to 60% of qualified sales opportunities are lost due to customer indecision

• Why dialing up FOMO doesn’t work, and what to do instead

• The “pings and echoes” technique to catch issues early

• The JOLT method for overcoming indecision

• Key lessons from The Challenger Sale

• Practical examples of how to apply these principles to close more deals

Brought to you by:

Enterpret—Transform customer feedback into product growth

Webflow—The web experience platform

Heap—Cross-platform product analytics that converts, engages, and retains customers

Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

Where to find Matt Dixon:

• LinkedIn: https://www.linkedin.com/in/matthewxdixon

• Website: https://www.jolteffect.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Matt’s background

(01:57) The research behind Matt’s books

(06:08) Insights from The JOLT Effect

(10:15) FOMO vs. FOMU

(18:18) An example of selling software

(26:04) The JOLT method Step 1: Judge their level of indecision

(29:41) The “pings and echoes” technique

(34:49) Step 2: Offer a recommendation

(38:36) Step 3: Limit the exploration

(41:43) Step 4: Take risk off the table

(45:58) When to hit the pause button with a customer

(47:27) Insights from The Challenger Sale

(49:07) An example of a challenger sale

(55:23) Where to find Matt

Referenced:

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854

The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

• Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition

Tiger King on Netflix: https://www.netflix.com/title/81115994

• Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral

• Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham

• Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias

• Omission bias: https://thedecisionlab.com/biases/omission-bias

• Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant

• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

• Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision

• Dentsply Sirona: https://www.dentsplysirona.com/

• “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE

• Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss:

• Why 40% to 60% of qualified sales opportunities are lost due to customer indecision

• Why dialing up FOMO doesn’t work, and what to do instead

• The “pings and echoes” technique to catch issues early

• The JOLT method for overcoming indecision

• Key lessons from The Challenger Sale

• Practical examples of how to apply these principles to close more deals

Brought to you by:

Enterpret—Transform customer feedback into product growth

Webflow—The web experience platform

Heap—Cross-platform product analytics that converts, engages, and retains customers

Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

Where to find Matt Dixon:

• LinkedIn: https://www.linkedin.com/in/matthewxdixon

• Website: https://www.jolteffect.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Matt’s background

(01:57) The research behind Matt’s books

(06:08) Insights from The JOLT Effect

(10:15) FOMO vs. FOMU

(18:18) An example of selling software

(26:04) The JOLT method Step 1: Judge their level of indecision

(29:41) The “pings and echoes” technique

(34:49) Step 2: Offer a recommendation

(38:36) Step 3: Limit the exploration

(41:43) Step 4: Take risk off the table

(45:58) When to hit the pause button with a customer

(47:27) Insights from The Challenger Sale

(49:07) An example of a challenger sale

(55:23) Where to find Matt

Referenced:

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854

The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

• Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition

Tiger King on Netflix: https://www.netflix.com/title/81115994

• Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral

• Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham

• Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias

• Omission bias: https://thedecisionlab.com/biases/omission-bias

• Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant

• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

• Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision

• Dentsply Sirona: https://www.dentsplysirona.com/

• “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE

• Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss:

• A simple framework for choosing where to work and what to work on

• The importance of “understand work”

• The “adjacent users” theory and how it can help you drive growth

• Advice for coaching product managers

• Invaluable lessons from his time at Instagram, Facebook, and YouTube

• Much more

Brought to you by:

Uizard—AI-powered prototyping for visionary product leaders

Mercury—The powerful and intuitive way for ambitious companies to bank

Vanta—Automate compliance. Simplify security.

Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

Where to find Bangaly Kaba:

• X: https://twitter.com/iambangaly

• LinkedIn: https://www.linkedin.com/in/iambangaly/

• Instagram: https://www.instagram.com/iambangaly/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Bangaly’s background

(06:31) Choosing where to work and what to work on

(08:39) The impact factor

(10:53) Evaluating the environment

(15:53) The manager component

(18:27) The skills part of the equation

(23:49) Advice on finding a mentor

(25:42) The power of “understand work”

(31:17) Operationalizing understand work

(37:55) Balancing understand work

(41:25) Managing complex change

(45:26) Effective management of product managers

(51:35) The role of product managers as coaches and team leaders

(54:52) Driving growth through flywheels and value proposition

(01:03:14) Understanding adjacent users

(01:08:41) The role of partnerships and SEO in Instagram’s early growth

(01:16:08) The secret behind Instagram’s growth

(01:25:37) Lessons from Facebook

(01:29:15) Failure corner

(01:31:58) Lightning round

Referenced:

• Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions

• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

• Casey Winters’s blog: https://caseyaccidental.com/

• Ben Thompson’s newsletter: https://stratechery.com/about/

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

• Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E

• What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/

• LeBron James: https://en.wikipedia.org/wiki/LeBron_James

• Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant

•  Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski

• John Calipari: https://en.wikipedia.org/wiki/John_Calipari

• Stripe: https://stripe.com/

• Chief: https://chief.com/

• Jobs to be done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user

• How the biggest consumer apps got their first 1,000 users: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got

• Alex Zhu on LinkedIn: https://www.linkedin.com/in/keepsilence/

• From Brush to Canvas with Alex Zhu of Musical.ly: https://www.youtube.com/watch?v=ey15v81pwII

• Selena Gomez on Instagram: https://www.instagram.com/selenagomez/

• Kim Kardashian on Instagram: https://www.instagram.com/kimkardashian/

• Rob Andrews on LinkedIn: https://www.linkedin.com/in/robby-andrews-64669720/

• Instagram’s growth speeds up as it hits 700 million users: https://techcrunch.com/2017/04/26/instagram-700-million-users/

Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

Deep Work: Rules for Focused Success in a Distracted World: https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692

Start at the End: How to Build Products That Create Change: https://www.amazon.com/Start-End-Products-Create-Change/dp/0525534423

• Flighty app: https://www.flightyapp.com/

• Adam Grant on Instagram: https://www.instagram.com/adamgrant/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss:

• A simple framework for choosing where to work and what to work on

• The importance of “understand work”

• The “adjacent users” theory and how it can help you drive growth

• Advice for coaching product managers

• Invaluable lessons from his time at Instagram, Facebook, and YouTube

• Much more

Brought to you by:

Uizard—AI-powered prototyping for visionary product leaders

Mercury—The powerful and intuitive way for ambitious companies to bank

Vanta—Automate compliance. Simplify security.

Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

Where to find Bangaly Kaba:

• X: https://twitter.com/iambangaly

• LinkedIn: https://www.linkedin.com/in/iambangaly/

• Instagram: https://www.instagram.com/iambangaly/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Bangaly’s background

(06:31) Choosing where to work and what to work on

(08:39) The impact factor

(10:53) Evaluating the environment

(15:53) The manager component

(18:27) The skills part of the equation

(23:49) Advice on finding a mentor

(25:42) The power of “understand work”

(31:17) Operationalizing understand work

(37:55) Balancing understand work

(41:25) Managing complex change

(45:26) Effective management of product managers

(51:35) The role of product managers as coaches and team leaders

(54:52) Driving growth through flywheels and value proposition

(01:03:14) Understanding adjacent users

(01:08:41) The role of partnerships and SEO in Instagram’s early growth

(01:16:08) The secret behind Instagram’s growth

(01:25:37) Lessons from Facebook

(01:29:15) Failure corner

(01:31:58) Lightning round

Referenced:

• Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions

• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

• Casey Winters’s blog: https://caseyaccidental.com/

• Ben Thompson’s newsletter: https://stratechery.com/about/

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

• Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E

• What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/

• LeBron James: https://en.wikipedia.org/wiki/LeBron_James

• Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant

•  Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski

• John Calipari: https://en.wikipedia.org/wiki/John_Calipari

• Stripe: https://stripe.com/

• Chief: https://chief.com/

• Jobs to be done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user

• How the biggest consumer apps got their first 1,000 users: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got

• Alex Zhu on LinkedIn: https://www.linkedin.com/in/keepsilence/

• From Brush to Canvas with Alex Zhu of Musical.ly: https://www.youtube.com/watch?v=ey15v81pwII

• Selena Gomez on Instagram: https://www.instagram.com/selenagomez/

• Kim Kardashian on Instagram: https://www.instagram.com/kimkardashian/

• Rob Andrews on LinkedIn: https://www.linkedin.com/in/robby-andrews-64669720/

• Instagram’s growth speeds up as it hits 700 million users: https://techcrunch.com/2017/04/26/instagram-700-million-users/

Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

Deep Work: Rules for Focused Success in a Distracted World: https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692

Start at the End: How to Build Products That Create Change: https://www.amazon.com/Start-End-Products-Create-Change/dp/0525534423

• Flighty app: https://www.flightyapp.com/

• Adam Grant on Instagram: https://www.instagram.com/adamgrant/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Extract Knowledge
Listen elsewhere

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:

• Why asking for what you want is so impactful

• Three steps to effectively ask for what you want

• Challenges that arise when people struggle to ask for what they want

• Why hearing “no” is a normal part of the process

• The “dream behind the complaint” technique for uncovering desires

• Kenneth’s experience of being fired three times from Slack

• How embracing fear and discomfort is key to getting what you want

• Why discipline is overrated

Brought to you by:

Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

Webflow—The web experience platform

Vanta—Automate compliance. Simplify security

Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger

Where to find Kenneth Berger:

• X: https://twitter.com/kberger

• Threads: https://www.threads.net/@kberger

• LinkedIn: https://www.linkedin.com/in/kberger/

• Website: https://kberger.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kenneth’s background

(04:31) The importance of asking for what you want

(06:36) Challenges that arise when people struggle to ask for what they want

(08:09) A personal example of failing to ask for what you want

(09:17) Signs this is a skill you need to work on

(10:49) How to get better at knowing what you want

(15:28) Why hearing “no” is a normal part of the process

(17:29) Getting a “yes” vs. a “hell yes”

(19:20) Step 1: Articulate what you want

(24:07) Doing an integrity check

(26:56) Step 2: Ask for what you want intentionally

(30:45) Understanding your influence

(34:48) Using complaints as inspiration

(36:24) Internal family systems

(38:00) Giving feedback

(41:24) Step 3: Accept the response

(45:22) Kenneth’s experience of being fired three times from Slack

(57:30) Advice on being the first PM at a company or startup

(01:04:58) Contrarian corner: anti-discipline

(01:05:52) Lightning round

Referenced:

• Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

• Internal Family Systems: https://ifs-institute.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• Leaders in Tech: https://leadersintech.org/

• The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

• DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

• Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny

• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

Break Point on Netflix: https://www.netflix.com/title/81569920

Living on Netflix: https://www.netflix.com/title/81582076

• Wimbledon tennis: https://www.wimbledon.com

• Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

• Tea From Taiwan: https://www.teafromtaiwan.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:

• Why asking for what you want is so impactful

• Three steps to effectively ask for what you want

• Challenges that arise when people struggle to ask for what they want

• Why hearing “no” is a normal part of the process

• The “dream behind the complaint” technique for uncovering desires

• Kenneth’s experience of being fired three times from Slack

• How embracing fear and discomfort is key to getting what you want

• Why discipline is overrated

Brought to you by:

Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

Webflow—The web experience platform

Vanta—Automate compliance. Simplify security

Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger

Where to find Kenneth Berger:

• X: https://twitter.com/kberger

• Threads: https://www.threads.net/@kberger

• LinkedIn: https://www.linkedin.com/in/kberger/

• Website: https://kberger.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kenneth’s background

(04:31) The importance of asking for what you want

(06:36) Challenges that arise when people struggle to ask for what they want

(08:09) A personal example of failing to ask for what you want

(09:17) Signs this is a skill you need to work on

(10:49) How to get better at knowing what you want

(15:28) Why hearing “no” is a normal part of the process

(17:29) Getting a “yes” vs. a “hell yes”

(19:20) Step 1: Articulate what you want

(24:07) Doing an integrity check

(26:56) Step 2: Ask for what you want intentionally

(30:45) Understanding your influence

(34:48) Using complaints as inspiration

(36:24) Internal family systems

(38:00) Giving feedback

(41:24) Step 3: Accept the response

(45:22) Kenneth’s experience of being fired three times from Slack

(57:30) Advice on being the first PM at a company or startup

(01:04:58) Contrarian corner: anti-discipline

(01:05:52) Lightning round

Referenced:

• Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

• Internal Family Systems: https://ifs-institute.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• Leaders in Tech: https://leadersintech.org/

• The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

• DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

• Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny

• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

Break Point on Netflix: https://www.netflix.com/title/81569920

Living on Netflix: https://www.netflix.com/title/81582076

• Wimbledon tennis: https://www.wimbledon.com

• Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

• Tea From Taiwan: https://www.teafromtaiwan.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:

• How Nubank builds a fanatical user base

• Tactics for driving word-of-mouth growth

• Measuring customer love through the Sean Ellis score

• The importance of strategic clarity

• The role of category design in creating successful products

• Why companies should strive to be “fundamentally different,” not “incrementally better”

• Nubank’s vision for an AI-powered banking future

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Mercury—The powerful and intuitive way for ambitious companies to bank

OneSchema—Import CSV data 10x faster

Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal

Where to find Jag Duggal:

• LinkedIn: https://www.linkedin.com/in/jagduggal/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jag’s background

(04:34) Nubank’s remarkable achievements

(06:01) Nubank’s product development process

(11:23) Nubank’s values

(12:16) Building products people love fanatically

(15:21) The Sean Ellis score

(21:27) An example project using the Sean Ellis score

(25:07) Picking up the phone and calling customers

(28:20) The importance of starting small and iterating

(30:42) Pushing back effectively

(34:10) Uncovering pain points through customer research

(37:53) An example of setting a clear hypothesis

(42:01) Developing a strategy

(52:16) “Be fundamentally different, not incrementally better”

(53:10) Category design

(57:37) Nubank’s founding story and goals for the future

(01:00:46) Advice for adding new product lines

(01:03:46) The future of fintech and banking

(01:09:23) AI corner

(01:12:34) Failure corner

(01:20:24) Key takeaways

(01:22:11) Lightning round

Referenced:

• Nubank: https://nubank.com.br/en/

• Coinbase: https://www.coinbase.com/

• Robinhood: https://www.robinhood.com/

• SoFi: https://www.sofi.com/

• Affirm: https://www.affirm.com/

• Lemonade: https://www.lemfi.com/

• Bank of America: https://www.bankofamerica.com/

• Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao

• Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea

• David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875

• Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira

• Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible

• Sequoia Capital: https://www.sequoiacap.com/

• Churrascaria: https://en.wikipedia.org/wiki/Churrascaria

• Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/

• Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

• Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

• How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/

• Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY

• The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

• How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher

Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619

Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

• Citi: https://www.citi.com/

• Santander Bank: https://www.santanderbank.com/

• Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

• Harvard Kennedy School: https://www.hks.harvard.edu/

• Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/

• Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg

• Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html

• Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272

From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/

The Gilded Age on HBO: https://www.hbo.com/the-gilded-age

• Lomi: https://lomi.com/

• Nubank careers: https://international.nubank.com.br/careers/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:

• How Nubank builds a fanatical user base

• Tactics for driving word-of-mouth growth

• Measuring customer love through the Sean Ellis score

• The importance of strategic clarity

• The role of category design in creating successful products

• Why companies should strive to be “fundamentally different,” not “incrementally better”

• Nubank’s vision for an AI-powered banking future

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Mercury—The powerful and intuitive way for ambitious companies to bank

OneSchema—Import CSV data 10x faster

Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal

Where to find Jag Duggal:

• LinkedIn: https://www.linkedin.com/in/jagduggal/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jag’s background

(04:34) Nubank’s remarkable achievements

(06:01) Nubank’s product development process

(11:23) Nubank’s values

(12:16) Building products people love fanatically

(15:21) The Sean Ellis score

(21:27) An example project using the Sean Ellis score

(25:07) Picking up the phone and calling customers

(28:20) The importance of starting small and iterating

(30:42) Pushing back effectively

(34:10) Uncovering pain points through customer research

(37:53) An example of setting a clear hypothesis

(42:01) Developing a strategy

(52:16) “Be fundamentally different, not incrementally better”

(53:10) Category design

(57:37) Nubank’s founding story and goals for the future

(01:00:46) Advice for adding new product lines

(01:03:46) The future of fintech and banking

(01:09:23) AI corner

(01:12:34) Failure corner

(01:20:24) Key takeaways

(01:22:11) Lightning round

Referenced:

• Nubank: https://nubank.com.br/en/

• Coinbase: https://www.coinbase.com/

• Robinhood: https://www.robinhood.com/

• SoFi: https://www.sofi.com/

• Affirm: https://www.affirm.com/

• Lemonade: https://www.lemfi.com/

• Bank of America: https://www.bankofamerica.com/

• Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao

• Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea

• David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875

• Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira

• Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible

• Sequoia Capital: https://www.sequoiacap.com/

• Churrascaria: https://en.wikipedia.org/wiki/Churrascaria

• Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/

• Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

• Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

• How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/

• Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY

• The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

• How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher

Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619

Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

• Citi: https://www.citi.com/

• Santander Bank: https://www.santanderbank.com/

• Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

• Harvard Kennedy School: https://www.hks.harvard.edu/

• Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/

• Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg

• Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html

• Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272

From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/

The Gilded Age on HBO: https://www.hbo.com/the-gilded-age

• Lomi: https://lomi.com/

• Nubank careers: https://international.nubank.com.br/careers/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:

• The most common traits among successful product managers

• The 3 W’s framework for PM career growth

• The Four A’s of leveling up in product management

• The right way to push back as a PM

• Common pitfalls that stall PM careers

• Vikrama’s advice for transitioning into product management

• Why intent alone is not enough

Brought to you by:

Uizard—AI-powered prototyping for visionary product leaders

Webflow—The web experience platform

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development

Where to find Vikrama Dhiman:

• X: https://twitter.com/vikramadhiman

• LinkedIn: https://www.linkedin.com/in/vikrama/

• Website: https://www.vikramadhiman.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Vikrama’s background

(03:56) Three common traits among great PMs

(07:09) The first W: What you produce

(15:40) The second W: What you bring to the table

(18:58) The third W: What’s your operating model?

(20:36) Three traits that make you a great PM to work with

(21:49) How to improve the quality and quantity of your outputs

(23:26) The art of the pushback

(26:55) Common factors that impede career growth

(33:39) Vikrama’s personal reflections

(39:33) Choosing which skill(s) to focus on developing

(46:28) The ambiguity of the PM role

(51:47) The 8 axis for PM growth

(56:57) Contrarian corner: Why intent alone is not enough

(59:30) Lightning round

Referenced:

• Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom

• How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock

• Gojek: https://www.gojek.com/en-id

• SQL: https://en.wikipedia.org/wiki/SQL

• Oracle: https://www.oracle.com/

• Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja

• Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id

• Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup

• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your

• Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/

• Workday: https://www.workday.com/

• Salesforce: https://www.salesforce.com/

Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681

Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X

Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK

Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F

• DramaBox: https://www.dramaboxapp.com/

Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/

Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF

• 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:

• The most common traits among successful product managers

• The 3 W’s framework for PM career growth

• The Four A’s of leveling up in product management

• The right way to push back as a PM

• Common pitfalls that stall PM careers

• Vikrama’s advice for transitioning into product management

• Why intent alone is not enough

Brought to you by:

Uizard—AI-powered prototyping for visionary product leaders

Webflow—The web experience platform

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development

Where to find Vikrama Dhiman:

• X: https://twitter.com/vikramadhiman

• LinkedIn: https://www.linkedin.com/in/vikrama/

• Website: https://www.vikramadhiman.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Vikrama’s background

(03:56) Three common traits among great PMs

(07:09) The first W: What you produce

(15:40) The second W: What you bring to the table

(18:58) The third W: What’s your operating model?

(20:36) Three traits that make you a great PM to work with

(21:49) How to improve the quality and quantity of your outputs

(23:26) The art of the pushback

(26:55) Common factors that impede career growth

(33:39) Vikrama’s personal reflections

(39:33) Choosing which skill(s) to focus on developing

(46:28) The ambiguity of the PM role

(51:47) The 8 axis for PM growth

(56:57) Contrarian corner: Why intent alone is not enough

(59:30) Lightning round

Referenced:

• Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom

• How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock

• Gojek: https://www.gojek.com/en-id

• SQL: https://en.wikipedia.org/wiki/SQL

• Oracle: https://www.oracle.com/

• Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja

• Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id

• Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup

• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your

• Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/

• Workday: https://www.workday.com/

• Salesforce: https://www.salesforce.com/

Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681

Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X

Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK

Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F

• DramaBox: https://www.dramaboxapp.com/

Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/

Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF

• 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Published 2024-05-05

Business strategy with Hamilton Helmer (author of 7 Powers)

68 min Transcript
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Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:

• Potential sources of power that startups should develop from an early stage

• Common misconceptions among companies about the types of power they possess

• How power relates to strategy

• The difference between a moat and a power

• Practical strategies for non-leaders to leverage insights about power and strategy in their work

• AI’s impact on competitive advantages and barriers to entry

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—Automate compliance. Simplify security

Paragon—Ship every SaaS integration your customers want

Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

Where to find Hamilton Helmer:

• X: https://twitter.com/hamiltonhelmer

• LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/

• Website: https://7powers.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Hamilton’s background

(04:08) When power becomes important

(08:24) How strategy relates to power

(12:09) How power informs strategy

(14:46) The sequence of powers

(21:13) Common misconceptions

(24:39) Network effects vs. network economies

(26:58) Uber’s success

(29:16) Moats vs. powers

(31:12) Strategies for non-leaders to leverage power and strategy

(37:51) Advice on how to become a strategic thinker

(39:27) AI’s impact on the seven powers

(45:43) Why moving fast is not a power

(50:24) Three things that create value in a company

(51:16) The debt trajectory of the U.S.

(56:35) Optimism for the future

(59:25) Lightning round

Referenced:

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann

• Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor

• Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/

• The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors

• 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/

• Strategy Capital: https://strategycapital.com/

• Warren Buffett: https://www.forbes.com/profile/warren-buffett/

• Charlie Munger: https://www.forbes.com/profile/charles-munger/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack

• Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6

•  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973

• Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html

• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

• What Is Strategy?: https://hbr.org/1996/11/what-is-strategy

• TSMC: https://www.tsmc.com/english

• Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System

• America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/

• Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke

• Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes

• Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter

Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982

The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311

The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X

American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX

• Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/

• Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland

• Ogilvy: https://www.ogilvy.com/

• Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005

• Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill

Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498

The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)

• Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:

• Potential sources of power that startups should develop from an early stage

• Common misconceptions among companies about the types of power they possess

• How power relates to strategy

• The difference between a moat and a power

• Practical strategies for non-leaders to leverage insights about power and strategy in their work

• AI’s impact on competitive advantages and barriers to entry

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—Automate compliance. Simplify security

Paragon—Ship every SaaS integration your customers want

Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

Where to find Hamilton Helmer:

• X: https://twitter.com/hamiltonhelmer

• LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/

• Website: https://7powers.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Hamilton’s background

(04:08) When power becomes important

(08:24) How strategy relates to power

(12:09) How power informs strategy

(14:46) The sequence of powers

(21:13) Common misconceptions

(24:39) Network effects vs. network economies

(26:58) Uber’s success

(29:16) Moats vs. powers

(31:12) Strategies for non-leaders to leverage power and strategy

(37:51) Advice on how to become a strategic thinker

(39:27) AI’s impact on the seven powers

(45:43) Why moving fast is not a power

(50:24) Three things that create value in a company

(51:16) The debt trajectory of the U.S.

(56:35) Optimism for the future

(59:25) Lightning round

Referenced:

7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann

• Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor

• Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/

• The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors

• 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/

• Strategy Capital: https://strategycapital.com/

• Warren Buffett: https://www.forbes.com/profile/warren-buffett/

• Charlie Munger: https://www.forbes.com/profile/charles-munger/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack

• Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6

•  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973

• Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html

• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

• What Is Strategy?: https://hbr.org/1996/11/what-is-strategy

• TSMC: https://www.tsmc.com/english

• Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System

• America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/

• Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke

• Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes

• Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter

Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982

The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311

The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X

American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX

• Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/

• Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland

• Ogilvy: https://www.ogilvy.com/

• Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005

• Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill

Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498

The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)

• Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

• What Annie learned from the late Daniel Kahneman

• The power of pre-mortems and “kill criteria”

• The relationship between money and happiness

• The power of “mental time travel”

• The nominal group technique for better decision quality

• How First Round Capital improved their decision-making process

• Many tactical decision-making frameworks

Brought to you by:

Vanta—Automate compliance. Simplify security.

UserTesting—Human understanding. Human experiences.

LinkedIn Ads—Reach professionals and drive results for your business

Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

Where to find Annie Duke:

• X: https://twitter.com/AnnieDuke

• LinkedIn: https://www.linkedin.com/in/annie-duke/

• Website: https://www.annieduke.com/

• Substack: https://www.annieduke.com/substack/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Annie’s background

(03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

(09:15) The importance of unconditional love in parenting

(15:15) Mental time travel and “nevertheless”

(20:06) The extent of improvement possible in decision-making 

(24:54) Independent brainstorming for better decisions

(35:36) Making sure people feel heard

(42:41) The “3Ds” framework to make better decisions

(44:49) Decision quality

(55:46) Improving decision-making at First Round Capital

(01:05:05) Using pre-mortems and kill criteria

(01:10:15) Making explicit what’s implicit

(01:10:55) The challenges of quitting and knowing when to walk away

(01:19:23) Where to find Annie

Referenced:

• Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

• Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

• Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

• Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

• Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

• Cass Sunstein on X: https://twitter.com/CassSunstein

• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

• First Round Capital: https://firstround.com/

• Brett Berson on X: https://twitter.com/brettberson

• Renegade Partners: https://www.renegadepartners.com/

• Renata Quintini on X: https://twitter.com/rquintini

• Roseanne Wincek on X: https://twitter.com/imthemusic

• Josh Kopelman on X: https://twitter.com/joshk

• Bill Trenchard on X: https://twitter.com/btrenchard

• Linnea Gandhi on X: https://twitter.com/linneagandhi

• Maurice Schweitzer on X: https://twitter.com/me_schweitzer

• Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

• Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

• Richard Thaler on X: https://twitter.com/R_Thaler

• Stewart Butterfield on X: https://twitter.com/stewart

• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

• How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

• The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

• The Alliance for Decision Education: https://alliancefordecisioneducation.org/

• Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

• What Annie learned from the late Daniel Kahneman

• The power of pre-mortems and “kill criteria”

• The relationship between money and happiness

• The power of “mental time travel”

• The nominal group technique for better decision quality

• How First Round Capital improved their decision-making process

• Many tactical decision-making frameworks

Brought to you by:

Vanta—Automate compliance. Simplify security.

UserTesting—Human understanding. Human experiences.

LinkedIn Ads—Reach professionals and drive results for your business

Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

Where to find Annie Duke:

• X: https://twitter.com/AnnieDuke

• LinkedIn: https://www.linkedin.com/in/annie-duke/

• Website: https://www.annieduke.com/

• Substack: https://www.annieduke.com/substack/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Annie’s background

(03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

(09:15) The importance of unconditional love in parenting

(15:15) Mental time travel and “nevertheless”

(20:06) The extent of improvement possible in decision-making 

(24:54) Independent brainstorming for better decisions

(35:36) Making sure people feel heard

(42:41) The “3Ds” framework to make better decisions

(44:49) Decision quality

(55:46) Improving decision-making at First Round Capital

(01:05:05) Using pre-mortems and kill criteria

(01:10:15) Making explicit what’s implicit

(01:10:55) The challenges of quitting and knowing when to walk away

(01:19:23) Where to find Annie

Referenced:

• Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

• Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

• Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

• Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

• Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

• Cass Sunstein on X: https://twitter.com/CassSunstein

• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

• First Round Capital: https://firstround.com/

• Brett Berson on X: https://twitter.com/brettberson

• Renegade Partners: https://www.renegadepartners.com/

• Renata Quintini on X: https://twitter.com/rquintini

• Roseanne Wincek on X: https://twitter.com/imthemusic

• Josh Kopelman on X: https://twitter.com/joshk

• Bill Trenchard on X: https://twitter.com/btrenchard

• Linnea Gandhi on X: https://twitter.com/linneagandhi

• Maurice Schweitzer on X: https://twitter.com/me_schweitzer

• Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

• Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

• Richard Thaler on X: https://twitter.com/R_Thaler

• Stewart Butterfield on X: https://twitter.com/stewart

• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

• How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

• The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

• The Alliance for Decision Education: https://alliancefordecisioneducation.org/

• Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:

• The story of being let go from Twitter after Elon’s acquisition

• How he turned Twitter’s stagnant culture around

• Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done

• Why Periscope failed

• Advice for building consumer products

• When to copy, when to innovate

Brought to you by:

Enterpret—Transform customer feedback into product growth

OneSchema—Import CSV data 10x faster

Heap—Cross-platform product analytics that convert, engage, and retain customers

Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

Where to find Kayvon Beykpour:

• X: https://twitter.com/kayvz

• LinkedIn: https://www.linkedin.com/in/kayvz/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kayvon’s background

(04:31) Getting Elon up to speed at Twitter

(11:34) The story of being let go from Twitter after Elon’s acquisition

(21:09) Changing the product culture at Twitter

(29:44) Building the “hide replies” feature

(32:02) Sacred crows, taking bold bets, and reigniting growth

(34:28) Aquihires and their impact

(42:40) Tips for successful acquisitions and staffing

(47:00) The limitations of frameworks like JTBD

(53:20) Signs you’ve gone too far with a framework

(57:44) Lessons from building Periscope

(01:00:41) Reasons why Periscope failed

(01:07:24) The challenges of implementing video at Twitter

(01:12:05) Copying ideas in good taste

(01:17:58) How to get better at building consumer products

(01:19:51) What Kayvon is building

(01:20:31) Lightning round

Referenced:

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3

• Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/

• Elon Musk on X: https://twitter.com/elonmusk

• Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/

• Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/

• Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.

• Keith Coleman on X: https://twitter.com/kcoleman

• Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/

• Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html

• John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/

• Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/

• Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/

• Chris Sacca’s website: https://chrissacca.com/

• Facebook Live: https://www.facebook.com/formedia/tools/facebook-live

• Kevin Hart on X: https://twitter.com/KevinHart4real

• Clubhouse: https://www.clubhouse.com/

• Vine: https://en.wikipedia.org/wiki/Vine_(service)

• Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/

• Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/

Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624

Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW

The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM

Star Trek official site: https://www.startrek.com/

Dune: part 2: https://www.dunemovie.com/

Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer

• Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942

Devs on Hulu: https://www.fxnetworks.com/shows/devs

• Nick Offerman on X: https://twitter.com/nick_offerman

3 Body Problem on Netflix: https://www.netflix.com/title/81024821

• Perplexity AI: https://www.perplexity.ai/

• Particle: https://www.particle.news/

• Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:

• The story of being let go from Twitter after Elon’s acquisition

• How he turned Twitter’s stagnant culture around

• Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done

• Why Periscope failed

• Advice for building consumer products

• When to copy, when to innovate

Brought to you by:

Enterpret—Transform customer feedback into product growth

OneSchema—Import CSV data 10x faster

Heap—Cross-platform product analytics that convert, engage, and retain customers

Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

Where to find Kayvon Beykpour:

• X: https://twitter.com/kayvz

• LinkedIn: https://www.linkedin.com/in/kayvz/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kayvon’s background

(04:31) Getting Elon up to speed at Twitter

(11:34) The story of being let go from Twitter after Elon’s acquisition

(21:09) Changing the product culture at Twitter

(29:44) Building the “hide replies” feature

(32:02) Sacred crows, taking bold bets, and reigniting growth

(34:28) Aquihires and their impact

(42:40) Tips for successful acquisitions and staffing

(47:00) The limitations of frameworks like JTBD

(53:20) Signs you’ve gone too far with a framework

(57:44) Lessons from building Periscope

(01:00:41) Reasons why Periscope failed

(01:07:24) The challenges of implementing video at Twitter

(01:12:05) Copying ideas in good taste

(01:17:58) How to get better at building consumer products

(01:19:51) What Kayvon is building

(01:20:31) Lightning round

Referenced:

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3

• Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/

• Elon Musk on X: https://twitter.com/elonmusk

• Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/

• Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/

• Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.

• Keith Coleman on X: https://twitter.com/kcoleman

• Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/

• Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html

• John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/

• Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/

• Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/

• Chris Sacca’s website: https://chrissacca.com/

• Facebook Live: https://www.facebook.com/formedia/tools/facebook-live

• Kevin Hart on X: https://twitter.com/KevinHart4real

• Clubhouse: https://www.clubhouse.com/

• Vine: https://en.wikipedia.org/wiki/Vine_(service)

• Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/

• Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/

Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624

Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW

The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM

Star Trek official site: https://www.startrek.com/

Dune: part 2: https://www.dunemovie.com/

Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer

• Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942

Devs on Hulu: https://www.fxnetworks.com/shows/devs

• Nick Offerman on X: https://twitter.com/nick_offerman

3 Body Problem on Netflix: https://www.netflix.com/title/81024821

• Perplexity AI: https://www.perplexity.ai/

• Particle: https://www.particle.news/

• Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss:

• The benefits of building robust relationships, in life and work

• The 15% rule, and how it will help you build better relationships

• The power of vulnerability

• Examples of how to practice vulnerability

• Why mental models you build early in life hold you back later

• The “three realities” and “the net”

• The art of inquiry

• Practical tips for avoiding defensiveness when getting feedback

• The impact of long Covid on Carole’s life

Brought to you by:

Eppo—Run reliable, impactful experiments

CommandBar—AI-powered user assistance for modern products and impatient users

The a16z Podcast—Featuring conversations with the founders and technologists shaping our future

Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

Where to find Carole Robin:

• LinkedIn: https://www.linkedin.com/in/carole-robin/

• Email: carolerobinllc@gmail.com

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Carole’s background

(05:17) The importance of building robust relationships

(10:20) The “Touchy Feely” course at Stanford

(13:29) An example of the in-class experience

(17:19) Leaders in Tech: developing interpersonal competence

(21:36) Progressive disclosure and the 15% rule

(24:28) Appropriate disclosure

(26:52) The power of vulnerability

(34:57) Admitting mistakes and sharing feelings

(37:08) Understanding mental models

(42:57) The “three realities” framework

(53:52) The power of feedback and personal change

(58:47) The art of inquiry

(01:03:27) How to get better at giving feedback

(01:07:47) Exercises and continued learning

(01:10:49) “Advice hinders relationships”

(01:16:49) Failure corner: AFOG

(01:20:30) Takeaways

(01:21:51) Lessons from long Covid

Referenced:

• How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships

Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ

• Leaders in Tech: https://leadersintech.org/

• Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows

• Steve Jobs: https://www.forbes.com/profile/steve-jobs/

• Sheryl Sandberg on X: https://twitter.com/sherylsandberg

• Ursula Burns: https://www.forbes.com/profile/ursula-burns/

• Application for Leaders in Tech: https://leadersintech.org/programs-and-applications

• Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html

• The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable

• The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/

• How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/

• Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://www.notion.so/pen-name/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

• Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2

• Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss:

• The benefits of building robust relationships, in life and work

• The 15% rule, and how it will help you build better relationships

• The power of vulnerability

• Examples of how to practice vulnerability

• Why mental models you build early in life hold you back later

• The “three realities” and “the net”

• The art of inquiry

• Practical tips for avoiding defensiveness when getting feedback

• The impact of long Covid on Carole’s life

Brought to you by:

Eppo—Run reliable, impactful experiments

CommandBar—AI-powered user assistance for modern products and impatient users

The a16z Podcast—Featuring conversations with the founders and technologists shaping our future

Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

Where to find Carole Robin:

• LinkedIn: https://www.linkedin.com/in/carole-robin/

• Email: carolerobinllc@gmail.com

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Carole’s background

(05:17) The importance of building robust relationships

(10:20) The “Touchy Feely” course at Stanford

(13:29) An example of the in-class experience

(17:19) Leaders in Tech: developing interpersonal competence

(21:36) Progressive disclosure and the 15% rule

(24:28) Appropriate disclosure

(26:52) The power of vulnerability

(34:57) Admitting mistakes and sharing feelings

(37:08) Understanding mental models

(42:57) The “three realities” framework

(53:52) The power of feedback and personal change

(58:47) The art of inquiry

(01:03:27) How to get better at giving feedback

(01:07:47) Exercises and continued learning

(01:10:49) “Advice hinders relationships”

(01:16:49) Failure corner: AFOG

(01:20:30) Takeaways

(01:21:51) Lessons from long Covid

Referenced:

• How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships

Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ

• Leaders in Tech: https://leadersintech.org/

• Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows

• Steve Jobs: https://www.forbes.com/profile/steve-jobs/

• Sheryl Sandberg on X: https://twitter.com/sherylsandberg

• Ursula Burns: https://www.forbes.com/profile/ursula-burns/

• Application for Leaders in Tech: https://leadersintech.org/programs-and-applications

• Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html

• The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable

• The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/

• How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/

• Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://www.notion.so/pen-name/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb

Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

• Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2

• Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss:

• How to effectively take ideas from 0 to 1 at larger companies

• How to craft a compelling vision

• The importance of vulnerability and feedback

• The role of intuition and product sense in making decisions

• How to practically communicate your vision

• How to balance collaboration and strong opinions

• Advice for building a strong team culture

• Pivoting with grace and enthusiasm

• The current AI revolution and its impact on PM

Brought to you by:

Paragon—Ship every SaaS integration your customers want

Lenny’s Talent Team—Hire the best product people. Find the best product gigs

Vanta—Automate compliance. Simplify security

Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

Where to find Mihika Kapoor:

• X: https://twitter.com/mihikapoor

• LinkedIn: https://www.linkedin.com/in/mihikakapoor/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Mihika’s background

(04:29) Core attributes of great product managers

(07:34) Crafting a compelling vision

(12:12) The vision behind FigJam 

(18:25) Delivering a vision without design or engineering skills

(21:52) Creating momentum

(26:36) The importance of strong conviction

(27:45) Direct communication

(32:48) Building hype

(42:20) Immersing yourself in user insights

(47:16) Operationalizing user insights  

(50:33) Caring deeply about what you build

(54:01) Finding passion in your work

(57:00) Building a strong culture

(01:07:07) Pivoting with grace and enthusiasm

(01:11:48) Design Nation

(01:13:15) Mihika’s weaknesses

(01:16:07) Building new products at larger companies

(01:20:50) Coming up with a great idea

(01:22:49) The key to going from 0 to 1

(01:26:47) Spreading the idea across the company

(01:29:15) Closing thoughts

(01:32:11) Lightning round

Referenced:

• Figma: https://www.figma.com/

• Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949

• FigJam: https://www.figma.com/figjam/

• Cognition: https://www.cognition-labs.com/

• Devin: https://www.cognition-labs.com/introducing-devin

• David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/

• Replit: https://replit.com/

• The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/

• Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/

• Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625

• Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/

• Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/

• Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/

• Config: https://config.figma.com/

• Dev Mode: https://www.figma.com/dev-mode/

• Asana: https://asana.com/

• Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/

• StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free

• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

• Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/

Design Disruptors: https://www.invisionapp.com/films/design-disruptors

• Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/

• Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/

• Design Nation: https://dn.businesstoday.org/

• Stuart Weitzman on X: https://twitter.com/StuartWeitzman

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

• Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot

• Hestia: https://en.wikipedia.org/wiki/Hestia

Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076

Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/

Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

Dune: Part 2: https://www.dunemovie.com/

• Arc browser: https://arc.net/

• Pika: https://pika.art/home

• The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss:

• How to effectively take ideas from 0 to 1 at larger companies

• How to craft a compelling vision

• The importance of vulnerability and feedback

• The role of intuition and product sense in making decisions

• How to practically communicate your vision

• How to balance collaboration and strong opinions

• Advice for building a strong team culture

• Pivoting with grace and enthusiasm

• The current AI revolution and its impact on PM

Brought to you by:

Paragon—Ship every SaaS integration your customers want

Lenny’s Talent Team—Hire the best product people. Find the best product gigs

Vanta—Automate compliance. Simplify security

Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

Where to find Mihika Kapoor:

• X: https://twitter.com/mihikapoor

• LinkedIn: https://www.linkedin.com/in/mihikakapoor/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Mihika’s background

(04:29) Core attributes of great product managers

(07:34) Crafting a compelling vision

(12:12) The vision behind FigJam 

(18:25) Delivering a vision without design or engineering skills

(21:52) Creating momentum

(26:36) The importance of strong conviction

(27:45) Direct communication

(32:48) Building hype

(42:20) Immersing yourself in user insights

(47:16) Operationalizing user insights  

(50:33) Caring deeply about what you build

(54:01) Finding passion in your work

(57:00) Building a strong culture

(01:07:07) Pivoting with grace and enthusiasm

(01:11:48) Design Nation

(01:13:15) Mihika’s weaknesses

(01:16:07) Building new products at larger companies

(01:20:50) Coming up with a great idea

(01:22:49) The key to going from 0 to 1

(01:26:47) Spreading the idea across the company

(01:29:15) Closing thoughts

(01:32:11) Lightning round

Referenced:

• Figma: https://www.figma.com/

• Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949

• FigJam: https://www.figma.com/figjam/

• Cognition: https://www.cognition-labs.com/

• Devin: https://www.cognition-labs.com/introducing-devin

• David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/

• Replit: https://replit.com/

• The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/

• Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/

• Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625

• Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/

• Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/

• Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/

• Config: https://config.figma.com/

• Dev Mode: https://www.figma.com/dev-mode/

• Asana: https://asana.com/

• Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/

• StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free

• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

• Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/

Design Disruptors: https://www.invisionapp.com/films/design-disruptors

• Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/

• Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/

• Design Nation: https://dn.businesstoday.org/

• Stuart Weitzman on X: https://twitter.com/StuartWeitzman

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

• Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot

• Hestia: https://en.wikipedia.org/wiki/Hestia

Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076

Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/

Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

Dune: Part 2: https://www.dunemovie.com/

• Arc browser: https://arc.net/

• Pika: https://pika.art/home

• The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

• Why founders need to adopt the mindset “Just don’t die”

• The most common reason startups fail

• When to pivot, and characteristics of a good pivot

• The concept of “tar pit ideas” and examples of bad startup ideas

• Why investors say no to startups

• The importance of market size in investment decisions

• The pitfalls of founders over-delegating

• Effective ways to talk to customers

• 20 ideas Dalton is looking to fund

Brought to you by:

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

Where to find Dalton Caldwell:

• X: https://twitter.com/daltonc

• LinkedIn: https://www.linkedin.com/in/daltoncaldwell/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Dalton’s background

(04:41) The value of simple advice

(07:04) Dalton’s advice: “Just don’t die”

(08:39) Knowing when to stop

(11:45) Deciding to pivot

(14:26) Characteristics of a good pivot

(17:53) Knowing when to pivot

(19:03) Zip’s journey and finding a market

(21:22) Why Dalton says to “Move towards the mountains and the desert”

(23:45) Tar pit ideas

(26:49) Understanding why investors say no

(29:14) The importance of market size

(32:16) Avoiding over-delegation and hiring senior people too early

(36:43) Why startups fail

(40:30) Effectively talking to customers

(45:17) Examples of startups hustling to talk to customers

(48:01) Patterns of successful startups

(52:05) YC’s Request for Startups

(55:37) Early days of Silicon Valley

(01:05:33) Contrarian corner: growth hacking for early startups

(01:09:28) Failure corner

(01:11:15) Closing thoughts

(01:12:22) Lightning round

Referenced:

• Y Combinator: https://www.ycombinator.com/

• Tiger Woods’s website: https://tigerwoods.com/

• Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

• Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

• Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

• Brex: https://www.brex.com/

• Retool: https://retool.com/

• Segment: https://segment.com/

• Mixpanel: https://mixpanel.com/

• Whatnot: https://www.whatnot.com/

• Andreessen Horowitz: https://a16z.com/

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

• Zip: https://ziphq.com/

• Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

• Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

• Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

• Foursquare: https://foursquare.com/

• Razorpay: https://razorpay.com/

• Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

• Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

• Milk Video: https://milkvideo.com/

• Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

• Collison installation: https://news.ycombinator.com/item?id=18400504

• Stripe: https://stripe.com/

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

• Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

• ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

• Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

• New space companies: https://www.ycombinator.com/rfs#new-space-companies

• A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

• Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

• New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

• Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

• Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

• Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Sam Altman on X: https://twitter.com/sama

• Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

• Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

• Marc Andreessen on X: https://twitter.com/pmarca

• Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

• Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

• Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

The Sopranos on HBO: https://www.hbo.com/the-sopranos

The Wire on HBO: https://www.hbo.com/the-wire

Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

• Oura ring: https://ouraring.com/

• Apple watch: https://www.apple.com/watch/

• SiPhox: https://siphoxhealth.com/

• Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

• How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

• The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

• Why founders need to adopt the mindset “Just don’t die”

• The most common reason startups fail

• When to pivot, and characteristics of a good pivot

• The concept of “tar pit ideas” and examples of bad startup ideas

• Why investors say no to startups

• The importance of market size in investment decisions

• The pitfalls of founders over-delegating

• Effective ways to talk to customers

• 20 ideas Dalton is looking to fund

Brought to you by:

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security

Coda—The all-in-one collaborative workspace

Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

Where to find Dalton Caldwell:

• X: https://twitter.com/daltonc

• LinkedIn: https://www.linkedin.com/in/daltoncaldwell/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Dalton’s background

(04:41) The value of simple advice

(07:04) Dalton’s advice: “Just don’t die”

(08:39) Knowing when to stop

(11:45) Deciding to pivot

(14:26) Characteristics of a good pivot

(17:53) Knowing when to pivot

(19:03) Zip’s journey and finding a market

(21:22) Why Dalton says to “Move towards the mountains and the desert”

(23:45) Tar pit ideas

(26:49) Understanding why investors say no

(29:14) The importance of market size

(32:16) Avoiding over-delegation and hiring senior people too early

(36:43) Why startups fail

(40:30) Effectively talking to customers

(45:17) Examples of startups hustling to talk to customers

(48:01) Patterns of successful startups

(52:05) YC’s Request for Startups

(55:37) Early days of Silicon Valley

(01:05:33) Contrarian corner: growth hacking for early startups

(01:09:28) Failure corner

(01:11:15) Closing thoughts

(01:12:22) Lightning round

Referenced:

• Y Combinator: https://www.ycombinator.com/

• Tiger Woods’s website: https://tigerwoods.com/

• Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

• Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

• Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

• Brex: https://www.brex.com/

• Retool: https://retool.com/

• Segment: https://segment.com/

• Mixpanel: https://mixpanel.com/

• Whatnot: https://www.whatnot.com/

• Andreessen Horowitz: https://a16z.com/

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

• Zip: https://ziphq.com/

• Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

• Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

• Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

• Foursquare: https://foursquare.com/

• Razorpay: https://razorpay.com/

• Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

• Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

• Milk Video: https://milkvideo.com/

• Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

• Collison installation: https://news.ycombinator.com/item?id=18400504

• Stripe: https://stripe.com/

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

• Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

• ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

• Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

• New space companies: https://www.ycombinator.com/rfs#new-space-companies

• A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

• Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

• New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

• Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

• Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

• Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Sam Altman on X: https://twitter.com/sama

• Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

• Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

• Marc Andreessen on X: https://twitter.com/pmarca

• Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

• Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

• Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

The Sopranos on HBO: https://www.hbo.com/the-sopranos

The Wire on HBO: https://www.hbo.com/the-wire

Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

• Oura ring: https://ouraring.com/

• Apple watch: https://www.apple.com/watch/

• SiPhox: https://siphoxhealth.com/

• Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

• How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

• The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

• How GitLab operationalizes transparency

• The philosophy behind recording and sharing team meetings on YouTube

• Their extensive public employee handbook

• GitLab’s core value of having “short toes”

• Challenges and advice for doing remote work well

• Strategies for ensuring effective communication in a remote work environment

• GitLab’s breadth-over-depth strategy

• The company’s unique approach to AI

• The value of using humor in high-stakes conversations

Brought to you by:

Orb—The flexible billing engine for modern pricing

Eppo—Run reliable, impactful experiments

Paragon—Ship every SaaS integration your customers want

Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

Where to find David DeSanto:

• X: https://twitter.com/david_desanto

• LinkedIn: https://www.linkedin.com/in/ddesanto/

• Threads: https://www.threads.net/@david.the.beard

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) David’s background

(04:20) Maintaining an epic beard

(05:29) Why GitLab publicly shares team meetings

(09:49) The GitLab Handbook

(11:30) GitLab’s issue tracker

(14:29) How to successfully build a culture of transparency

(18:11) Benefits of operating with transparency

(19:55) The value of building in public

(21:53) How GitLab implements their core value of kindness

(25:16) What it means to have “short toes”

(27:41) Other core values

(32:16) Common reasons for not fitting in at GitLab

(34:42) Advice for remote teams

(42:04) Advice for getting into product

(43:52) Advice for PMs who are struggling in a remote world

(48:25) Specific tools that help with remote work

(53:13) Time zones and remote work

(57:18) Breadth-over-depth strategy

(01:04:14) AI at GitLab

(01:13:11) GitLab’s products and solutions

(01:14:54) Lightning round

Referenced:

• GitLab: https://about.gitlab.com/

• UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

• The GitLab Handbook: https://handbook.gitlab.com/

• Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

• Y Combinator: https://www.ycombinator.com/

• GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

• Salesforce: https://www.salesforce.com/

• GitLab values: https://handbook.gitlab.com/handbook/values

• GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

• GitLab direction: https://about.gitlab.com/direction/

• Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

• The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• HubSpot: https://www.hubspot.com/

Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

• Open-core model: https://en.wikipedia.org/wiki/Open-core_model

• GitLab Duo: https://about.gitlab.com/gitlab-duo/

• GitLab Docs: https://docs.gitlab.com/

• Anthropic: https://www.anthropic.com/

• GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

• The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

• Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

• The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

• Artifact News: https://artifact.news/

• Superhuman: https://superhuman.com/

• Arc browser: https://arc.net/

• An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

• How GitLab operationalizes transparency

• The philosophy behind recording and sharing team meetings on YouTube

• Their extensive public employee handbook

• GitLab’s core value of having “short toes”

• Challenges and advice for doing remote work well

• Strategies for ensuring effective communication in a remote work environment

• GitLab’s breadth-over-depth strategy

• The company’s unique approach to AI

• The value of using humor in high-stakes conversations

Brought to you by:

Orb—The flexible billing engine for modern pricing

Eppo—Run reliable, impactful experiments

Paragon—Ship every SaaS integration your customers want

Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

Where to find David DeSanto:

• X: https://twitter.com/david_desanto

• LinkedIn: https://www.linkedin.com/in/ddesanto/

• Threads: https://www.threads.net/@david.the.beard

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) David’s background

(04:20) Maintaining an epic beard

(05:29) Why GitLab publicly shares team meetings

(09:49) The GitLab Handbook

(11:30) GitLab’s issue tracker

(14:29) How to successfully build a culture of transparency

(18:11) Benefits of operating with transparency

(19:55) The value of building in public

(21:53) How GitLab implements their core value of kindness

(25:16) What it means to have “short toes”

(27:41) Other core values

(32:16) Common reasons for not fitting in at GitLab

(34:42) Advice for remote teams

(42:04) Advice for getting into product

(43:52) Advice for PMs who are struggling in a remote world

(48:25) Specific tools that help with remote work

(53:13) Time zones and remote work

(57:18) Breadth-over-depth strategy

(01:04:14) AI at GitLab

(01:13:11) GitLab’s products and solutions

(01:14:54) Lightning round

Referenced:

• GitLab: https://about.gitlab.com/

• UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

• The GitLab Handbook: https://handbook.gitlab.com/

• Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

• Y Combinator: https://www.ycombinator.com/

• GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

• Salesforce: https://www.salesforce.com/

• GitLab values: https://handbook.gitlab.com/handbook/values

• GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

• GitLab direction: https://about.gitlab.com/direction/

• Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

• The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• HubSpot: https://www.hubspot.com/

Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

• Open-core model: https://en.wikipedia.org/wiki/Open-core_model

• GitLab Duo: https://about.gitlab.com/gitlab-duo/

• GitLab Docs: https://docs.gitlab.com/

• Anthropic: https://www.anthropic.com/

• GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

• The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

• Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

• The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

• Artifact News: https://artifact.news/

• Superhuman: https://superhuman.com/

• Arc browser: https://arc.net/

• An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss:

• Why product-market fit (PMF) matters

• First Round Capital’s four-part PMF framework

• Level one: Nascent product-market fit

• Level two: Developing product-market fit

• Level three: Strong product-market fit

• Level four: Extreme product-market fit

• Examples of companies at each level

• How to know if you’re stuck at a level, and how to get unstuck

• What to change if you’re stuck: persona, problem, promise, and product

• The goals and challenges at each stage

Brought to you by:

WorkOS—The modern API for auth and user identity

Eppo—Run reliable, impactful experiments

CommandBar—AI-powered user assistance for modern products and impatient users

Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

Where to find Todd Jackson:

• X: https://twitter.com/tjack

• LinkedIn: https://www.linkedin.com/in/toddj0/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Todd’s background

(06:07) First Round Capital’s PMF framework

(09:07) Why product-market fit is so important

(11:02) Who can benefit from this framework

(12:55) The product-market fit method

(16:54) Broad overview of the framework

(21:35) Level one: nascent product-market fit

(33:16) The four P’s

(39:13) Level two: developing product-market fit

(49:13) Signs you’re stuck at level two, and what to do

(55:12) Level three: strong product-market fit

(01:00:17) Signs you’re stuck at level three, and what to do

(01:02:22) Level four: extreme product-market fit

(01:06:55) Rough timelines for each level

(01:11:18) A quick recap of the framework

(01:12:15) Diving deeper on the four P’s: what to do if you’re stuck

(01:13:56) Dollar-driven discovery

(01:25:11) Apply for the product-market-fit method program

Referenced:

• First Round: https://firstround.com/

• Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup

• Dropbox: https://www.dropbox.com/

• Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/

• How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

• How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea

• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

• How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

• A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

• Product-market fit method: http://pmf.firstround.com/

• Stripe: https://stripe.com/

• Plaid: https://plaid.com/

• Paths to PMF: https://review.firstround.com/series/product-market-fit/

• WeWork: https://www.wework.com/

• Casper: https://casper.com/

• Vanta: https://www.vanta.com/

• Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

• Ramp: https://ramp.com/

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

• Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/

• Lattice: https://lattice.com/

• Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/

• Positioning: https://www.lennysnewsletter.com/p/positioning

• Retool: https://retool.com/

• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

• Persona: https://withpersona.com/

• Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/

• Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/

• Looker: https://en.wikipedia.org/wiki/Looker_(company)

• Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/

• Ironclad: https://ironcladapp.com/

• Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ

• Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/

• Verkada: https://www.verkada.com/

• Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

• Databricks: https://www.databricks.com/

• Stripe Radar: https://stripe.com/radar

• Stripe Atlas: https://stripe.com/atlas

• Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader

• Cash App: https://cash.app/

• Square Checking: https://squareup.com/us/en/campaign/banking/checking

• Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital

• Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/

• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

• Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/

• Simon Kucher: https://www.simon-kucher.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss:

• Why product-market fit (PMF) matters

• First Round Capital’s four-part PMF framework

• Level one: Nascent product-market fit

• Level two: Developing product-market fit

• Level three: Strong product-market fit

• Level four: Extreme product-market fit

• Examples of companies at each level

• How to know if you’re stuck at a level, and how to get unstuck

• What to change if you’re stuck: persona, problem, promise, and product

• The goals and challenges at each stage

Brought to you by:

WorkOS—The modern API for auth and user identity

Eppo—Run reliable, impactful experiments

CommandBar—AI-powered user assistance for modern products and impatient users

Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

Where to find Todd Jackson:

• X: https://twitter.com/tjack

• LinkedIn: https://www.linkedin.com/in/toddj0/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Todd’s background

(06:07) First Round Capital’s PMF framework

(09:07) Why product-market fit is so important

(11:02) Who can benefit from this framework

(12:55) The product-market fit method

(16:54) Broad overview of the framework

(21:35) Level one: nascent product-market fit

(33:16) The four P’s

(39:13) Level two: developing product-market fit

(49:13) Signs you’re stuck at level two, and what to do

(55:12) Level three: strong product-market fit

(01:00:17) Signs you’re stuck at level three, and what to do

(01:02:22) Level four: extreme product-market fit

(01:06:55) Rough timelines for each level

(01:11:18) A quick recap of the framework

(01:12:15) Diving deeper on the four P’s: what to do if you’re stuck

(01:13:56) Dollar-driven discovery

(01:25:11) Apply for the product-market-fit method program

Referenced:

• First Round: https://firstround.com/

• Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup

• Dropbox: https://www.dropbox.com/

• Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/

• How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

• How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea

• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

• How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

• A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

• Product-market fit method: http://pmf.firstround.com/

• Stripe: https://stripe.com/

• Plaid: https://plaid.com/

• Paths to PMF: https://review.firstround.com/series/product-market-fit/

• WeWork: https://www.wework.com/

• Casper: https://casper.com/

• Vanta: https://www.vanta.com/

• Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

• Ramp: https://ramp.com/

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

• Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/

• Lattice: https://lattice.com/

• Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/

• Positioning: https://www.lennysnewsletter.com/p/positioning

• Retool: https://retool.com/

• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

• Persona: https://withpersona.com/

• Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/

• Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/

• Looker: https://en.wikipedia.org/wiki/Looker_(company)

• Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/

• Ironclad: https://ironcladapp.com/

• Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ

• Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/

• Verkada: https://www.verkada.com/

• Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

• Databricks: https://www.databricks.com/

• Stripe Radar: https://stripe.com/radar

• Stripe Atlas: https://stripe.com/atlas

• Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader

• Cash App: https://cash.app/

• Square Checking: https://squareup.com/us/en/campaign/banking/checking

• Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital

• Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/

• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

• Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/

• Simon Kucher: https://www.simon-kucher.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Claire Vo is the chief product officer at LaunchDarkly and the founder of ChatPRD, likely the most popular PM-specific AI product out there. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has founded and managed two other companies, Pretty HQ and Experiment Engine, the latter of which Optimizely acquired in 2017. In our conversation, we discuss:

• Knowing what you want in your career and being clear about it

• Finding your zone of genius and how to operate within it

• How to maintain a fast pace in larger companies

• How to make it easy for your boss to help you achieve your goals

• Advice for navigating the tech industry as a woman

• The role of a CPTO and the benefits it brings to organizations

• Why she built ChatPRD

• Tips for building your own AI tools

• The impact of AI on product management and what skills will continue to be important

Brought to you by:

Orb—The flexible billing engine for modern pricing

Dovetail—Bring your customer into every decision

Vanta—Automate compliance. Simplify security

Find the full transcript at: https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor

Where to find Claire Vo:

• X: https://twitter.com/clairevo

• LinkedIn: https://www.linkedin.com/in/clairevo/

• TikTok: https://www.tiktok.com/@chiefproductofficer

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Claire’s background

(04:50) How to achieve career progression

(10:11) Avoiding promotion obsession

(13:50) How Claire stepped into leadership roles

(17:24) Operating in your zone of genius

(23:03) How to maintain a fast pace

(27:46) Setting a high bar for quality and talent

(29:54) Normalizing feedback

(33:09) Being a woman in tech

(47:09) The role of a CPTO

(54:19) Building ChatPRD

(59:39) Tips for building a GPT

(01:02:27) The impact of AI on product management

(01:08:08) How AI is changing the product management role

(01:14:36) Efficiency gains with ChatPRD

(01:16:39) Contrarian corner: sales-led product organizations

(01:20:11) Lightning round

Referenced:

• LaunchDarkly: https://launchdarkly.com/

• Define your zone of genius: Laura Garnett at TEDxMillRiver: https://www.youtube.com/watch?v=gQ7_r2oWlrw

• Energy Audit: https://beta.mocharymethod.com/blog-post/energy-audit

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/

• Optimizely: https://www.optimizely.com/

• GitLab: https://about.gitlab.com/

• ChatPRD: https://www.chatprd.ai/

• You should be playing with GPTs at work: https://www.lennysnewsletter.com/p/you-should-be-playing-with-gpts-at

• SpaceX’s Starship: https://www.spacex.com/vehicles/starship/

• GitHub Copilot: https://github.com/features/copilot

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennyspodcast.com/product-management-theater-marty-cagan-silicon-valley-product-group/

High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Stripe Press: https://press.stripe.com/

Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327

Poor Things: https://www.imdb.com/title/tt14230458/

Mythic Quest on AppleTV+: https://tv.apple.com/us/show/mythic-quest/umc.cmc.1nfdfd5zlk05fo1bwwetzldy3

Silicon Valley on HBO: https://www.hbo.com/silicon-valley

• Chrysler Pacifica: https://www.chrysler.com/pacifica.html

• Waymo: https://waymo.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Claire Vo is the chief product officer at LaunchDarkly and the founder of ChatPRD, likely the most popular PM-specific AI product out there. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has founded and managed two other companies, Pretty HQ and Experiment Engine, the latter of which Optimizely acquired in 2017. In our conversation, we discuss:

• Knowing what you want in your career and being clear about it

• Finding your zone of genius and how to operate within it

• How to maintain a fast pace in larger companies

• How to make it easy for your boss to help you achieve your goals

• Advice for navigating the tech industry as a woman

• The role of a CPTO and the benefits it brings to organizations

• Why she built ChatPRD

• Tips for building your own AI tools

• The impact of AI on product management and what skills will continue to be important

Brought to you by:

Orb—The flexible billing engine for modern pricing

Dovetail—Bring your customer into every decision

Vanta—Automate compliance. Simplify security

Find the full transcript at: https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor

Where to find Claire Vo:

• X: https://twitter.com/clairevo

• LinkedIn: https://www.linkedin.com/in/clairevo/

• TikTok: https://www.tiktok.com/@chiefproductofficer

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Claire’s background

(04:50) How to achieve career progression

(10:11) Avoiding promotion obsession

(13:50) How Claire stepped into leadership roles

(17:24) Operating in your zone of genius

(23:03) How to maintain a fast pace

(27:46) Setting a high bar for quality and talent

(29:54) Normalizing feedback

(33:09) Being a woman in tech

(47:09) The role of a CPTO

(54:19) Building ChatPRD

(59:39) Tips for building a GPT

(01:02:27) The impact of AI on product management

(01:08:08) How AI is changing the product management role

(01:14:36) Efficiency gains with ChatPRD

(01:16:39) Contrarian corner: sales-led product organizations

(01:20:11) Lightning round

Referenced:

• LaunchDarkly: https://launchdarkly.com/

• Define your zone of genius: Laura Garnett at TEDxMillRiver: https://www.youtube.com/watch?v=gQ7_r2oWlrw

• Energy Audit: https://beta.mocharymethod.com/blog-post/energy-audit

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/

• Optimizely: https://www.optimizely.com/

• GitLab: https://about.gitlab.com/

• ChatPRD: https://www.chatprd.ai/

• You should be playing with GPTs at work: https://www.lennysnewsletter.com/p/you-should-be-playing-with-gpts-at

• SpaceX’s Starship: https://www.spacex.com/vehicles/starship/

• GitHub Copilot: https://github.com/features/copilot

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennyspodcast.com/product-management-theater-marty-cagan-silicon-valley-product-group/

High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Stripe Press: https://press.stripe.com/

Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327

Poor Things: https://www.imdb.com/title/tt14230458/

Mythic Quest on AppleTV+: https://tv.apple.com/us/show/mythic-quest/umc.cmc.1nfdfd5zlk05fo1bwwetzldy3

Silicon Valley on HBO: https://www.hbo.com/silicon-valley

• Chrysler Pacifica: https://www.chrysler.com/pacifica.html

• Waymo: https://waymo.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, built ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16 million users), and also founded and writes for OnStartups, a top-ranking startup blog and community with more than 1M members. He’s also invested in 100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss:

• The biggest lessons he has learned from building HubSpot

• The importance of leaning into your strengths

• Dharmesh’s data-oriented approach to public speaking

• How he developed HubSpot’s culture code

• The decision-making process at HubSpot

• His contrarian approach to building products

• Why founders and product teams are all fighting the second law of thermodynamics

• How “flash tags” can save your teams time

• How to decide what ideas are worth investing in

Brought to you by:

Explo—Embed customer-facing analytics in your product

Vanta—Automate compliance. Simplify security

LinkedIn Ads—Reach professionals and drive results for your business

Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

Where to find Dharmesh Shah:

• X: https://twitter.com/dharmesh

• LinkedIn: https://www.linkedin.com/in/dharmesh/

• Website: https://dharmesh.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Dharmesh’s background

(04:20) Fun facts about Dharmesh

(06:31) His data-oriented approach to public speaking

(11:45) Advice for adding humor to your presentations

(15:28) Why he has no direct reports

(18:46) You can shape the universe to your liking

(20:02) Lessons from building HubSpot

(23:43) Contrarian ways of running a company

(37:26) Fighting the second law of thermodynamics

(40:29) The importance of simplicity in running a business

(45:22) Succeeding in the SMB market

(50:29) Zigging when others are zagging

(54:17) When it makes sense to go “wide and deep”

(57:33) Using flashtags to communicate opinions

(01:02:44) HubSpot’s decision-making process

(01:09:41) Deciding what ideas to invest in

(01:15:26) Defining and maintaining company culture

(01:30:46) The potential of AI

(01:37:03) Practical advice for learning AI

(01:40:07) Where to find Dharmesh

Referenced:

• WordPlay: https://wordplay.com/article/unlimited

• ChatSpot: https://chatspot.ai/

• Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: https://www.businesstoday.in/technology/news/story/indian-origin-entrepreneur-buys-chatcom-for-over-10-million-then-sells-donates-250000-to-khan-academy-382907-2023-05-26

• Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/

• The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/

• SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/

• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/

• First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/

• The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics

• What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business

• Shopify: https://www.shopify.com/

• Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/

• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

• What it means to “disagree and commit”: https://news.ycombinator.com/item?id=16949021

• A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite

• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/

• Zip: https://ziphq.com/

• The HubSpot Culture Code: Creating a Company We Love: https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx

• How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie

• What is SQL?: https://aws.amazon.com/what-is/sql/

• GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, built ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16 million users), and also founded and writes for OnStartups, a top-ranking startup blog and community with more than 1M members. He’s also invested in 100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss:

• The biggest lessons he has learned from building HubSpot

• The importance of leaning into your strengths

• Dharmesh’s data-oriented approach to public speaking

• How he developed HubSpot’s culture code

• The decision-making process at HubSpot

• His contrarian approach to building products

• Why founders and product teams are all fighting the second law of thermodynamics

• How “flash tags” can save your teams time

• How to decide what ideas are worth investing in

Brought to you by:

Explo—Embed customer-facing analytics in your product

Vanta—Automate compliance. Simplify security

LinkedIn Ads—Reach professionals and drive results for your business

Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

Where to find Dharmesh Shah:

• X: https://twitter.com/dharmesh

• LinkedIn: https://www.linkedin.com/in/dharmesh/

• Website: https://dharmesh.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Dharmesh’s background

(04:20) Fun facts about Dharmesh

(06:31) His data-oriented approach to public speaking

(11:45) Advice for adding humor to your presentations

(15:28) Why he has no direct reports

(18:46) You can shape the universe to your liking

(20:02) Lessons from building HubSpot

(23:43) Contrarian ways of running a company

(37:26) Fighting the second law of thermodynamics

(40:29) The importance of simplicity in running a business

(45:22) Succeeding in the SMB market

(50:29) Zigging when others are zagging

(54:17) When it makes sense to go “wide and deep”

(57:33) Using flashtags to communicate opinions

(01:02:44) HubSpot’s decision-making process

(01:09:41) Deciding what ideas to invest in

(01:15:26) Defining and maintaining company culture

(01:30:46) The potential of AI

(01:37:03) Practical advice for learning AI

(01:40:07) Where to find Dharmesh

Referenced:

• WordPlay: https://wordplay.com/article/unlimited

• ChatSpot: https://chatspot.ai/

• Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: https://www.businesstoday.in/technology/news/story/indian-origin-entrepreneur-buys-chatcom-for-over-10-million-then-sells-donates-250000-to-khan-academy-382907-2023-05-26

• Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/

• The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/

• SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/

• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/

• First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/

• The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics

• What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business

• Shopify: https://www.shopify.com/

• Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/

• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

• What it means to “disagree and commit”: https://news.ycombinator.com/item?id=16949021

• A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite

• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/

• Zip: https://ziphq.com/

• The HubSpot Culture Code: Creating a Company We Love: https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx

• How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie

• What is SQL?: https://aws.amazon.com/what-is/sql/

• GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Matt Abrahams is a renowned communication expert, with decades of teaching, coaching, and consulting experience. At Stanford University, he teaches a business school class on strategic communication. Beyond academia, he’s a sought-after keynote speaker and consultant, guiding presenters from IPO road shows to prestigious platforms like TED, the World Economic Forum, and the United Nations. His acclaimed podcast, Think Fast, Talk Smart, garners millions of listeners, and his book, Think Faster, Talk Smarter, equips speakers with practical skills for impromptu success. With a previous bestseller, Speaking Up Without Freaking Out, Matt has empowered countless individuals to speak confidently and authentically. In our conversation, we discuss:

• The concept of “daring to be dull”

• The power of visualization to desensitize oneself to speaking situations

• Managing negative self-talk

• The WHAT structure for delivering toasts (why we are here, how you are connected, anecdote, thanks)

• The ADD structure for Q&As (answer, detailed example, describe relevance)

• Breathing techniques to reduce anxiety, such as the double exhale

• Concrete speaking structures like What? So What? Now What? and the Four I’s (information, impact, invitation, implications)

• Much more

Brought to you by:

Sprig—Build a product people love

Dovetail—Bring your customer into every decision

Coda—Meet the evolution of docs

Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-speak-more-confidently-and

Where to find Matt Abrahams:

• X: https://twitter.com/tftsthepod

• LinkedIn: https://www.linkedin.com/in/maabrahams/

• Website: https://mattabrahams.com/

• Podcast: https://open.spotify.com/show/6ll0MwobDt1JW9gYaOONEo

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Matt’s background

(04:50) Techniques for managing anxiety in public speaking

(10:57) Dare to be dull

(13:40) Reframing anxiety as excitement

(16:08) Using mantras to boost confidence

(18:45) Managing negative self-talk

(20:03) Normalizing speaking anxiety

(23:12) Using conversation as a communication technique

(24:52) Using the double-exhale breathing technique

(28:29) Getting present-oriented

(29:46) Using tongue twisters

(33:34) Broad advice for speaking on the spot

(38:35) The PREP structure

(38:59) The What? So What? Now What? structure

(42:10) Toastmasters and improv

(45:31) Getting better at small talk

(51:05) The importance of sharing back

(52:33) Giving feedback

(56:31) Improving toasts and tributes

(01:02:57) Mastering Q&A sessions

(01:07:25) Apologizing effectively

(01:09:29) Closing thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Matt Abrahams is a renowned communication expert, with decades of teaching, coaching, and consulting experience. At Stanford University, he teaches a business school class on strategic communication. Beyond academia, he’s a sought-after keynote speaker and consultant, guiding presenters from IPO road shows to prestigious platforms like TED, the World Economic Forum, and the United Nations. His acclaimed podcast, Think Fast, Talk Smart, garners millions of listeners, and his book, Think Faster, Talk Smarter, equips speakers with practical skills for impromptu success. With a previous bestseller, Speaking Up Without Freaking Out, Matt has empowered countless individuals to speak confidently and authentically. In our conversation, we discuss:

• The concept of “daring to be dull”

• The power of visualization to desensitize oneself to speaking situations

• Managing negative self-talk

• The WHAT structure for delivering toasts (why we are here, how you are connected, anecdote, thanks)

• The ADD structure for Q&As (answer, detailed example, describe relevance)

• Breathing techniques to reduce anxiety, such as the double exhale

• Concrete speaking structures like What? So What? Now What? and the Four I’s (information, impact, invitation, implications)

• Much more

Brought to you by:

Sprig—Build a product people love

Dovetail—Bring your customer into every decision

Coda—Meet the evolution of docs

Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-speak-more-confidently-and

Where to find Matt Abrahams:

• X: https://twitter.com/tftsthepod

• LinkedIn: https://www.linkedin.com/in/maabrahams/

• Website: https://mattabrahams.com/

• Podcast: https://open.spotify.com/show/6ll0MwobDt1JW9gYaOONEo

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Matt’s background

(04:50) Techniques for managing anxiety in public speaking

(10:57) Dare to be dull

(13:40) Reframing anxiety as excitement

(16:08) Using mantras to boost confidence

(18:45) Managing negative self-talk

(20:03) Normalizing speaking anxiety

(23:12) Using conversation as a communication technique

(24:52) Using the double-exhale breathing technique

(28:29) Getting present-oriented

(29:46) Using tongue twisters

(33:34) Broad advice for speaking on the spot

(38:35) The PREP structure

(38:59) The What? So What? Now What? structure

(42:10) Toastmasters and improv

(45:31) Getting better at small talk

(51:05) The importance of sharing back

(52:33) Giving feedback

(56:31) Improving toasts and tributes

(01:02:57) Mastering Q&A sessions

(01:07:25) Apologizing effectively

(01:09:29) Closing thoughts

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kunal Shah is one of the most well-known and admired product leaders in India. He is the CEO and founder of CRED, an Indian-based fintech startup valued at over $6 billion. Prior to CRED, he founded three other startups, including Freecharge, which he sold for over $400 million to Snapdeal. He has also been an advisor to India’s most influential organizations. In our conversation, we discuss:

• The prevalence of successful Indian immigrants in top CEO roles across the tech industry

• Why companies in India can grow DAUs but not ARPU—and what that means for building products for India

• What most sets India’s market apart

• Challenges and opportunities in the Indian market

• The Delta 4 framework for building new products

• Lessons from building CRED so far

• The power of curiosity and second-order thinking

• Lessons from failure

Brought to you by:

WorkOS—The modern API for auth and user identity

Orb—The flexible billing engine for modern pricing

Dovetail—Bring your customer into every decision

Find the transcript and references at: https://www.lennysnewsletter.com/p/kunal-shah-on-winning-in-india-second

Where to find Kunal Shah:

• X: https://twitter.com/kunalb11

• LinkedIn: https://www.linkedin.com/in/kunalshah1/

• Podcast: https://www.youtube.com/@CRED_club

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kunal’s background

(04:22) The Delta 4 framework

(11:00) The success of Indian CEOs in the U.S.

(19:55) Challenges and opportunities in India

(23:04) DAUs vs. ARPU in Indian markets

(25:50) The perception of time in India

(27:55) The curse of focus in Asian markets

(30:33) Challenges and opportunities in India (continued)

(33:23) Lessons learned from building CRED

(36:40) Profit pools can provide valuable insights into the values of a country

(37:55) Founders’ role in company growth

(39:55) Profitability and Indian business culture

(43:24) Advice for staying positive amid criticism

(44:41) The promising market in India

(47:35) The power of curiosity

(52:59) Who Kunal looks up to

(55:31) Kunal’s favorite sources of content

(58:42) Asking great questions

(01:02:54) Contrarian corner: Wealth is nothing but storage of energy

(01:05:26) Failure corner

(01:08:57) Closing thoughts: Share your learnings

(01:09:38) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Kunal Shah is one of the most well-known and admired product leaders in India. He is the CEO and founder of CRED, an Indian-based fintech startup valued at over $6 billion. Prior to CRED, he founded three other startups, including Freecharge, which he sold for over $400 million to Snapdeal. He has also been an advisor to India’s most influential organizations. In our conversation, we discuss:

• The prevalence of successful Indian immigrants in top CEO roles across the tech industry

• Why companies in India can grow DAUs but not ARPU—and what that means for building products for India

• What most sets India’s market apart

• Challenges and opportunities in the Indian market

• The Delta 4 framework for building new products

• Lessons from building CRED so far

• The power of curiosity and second-order thinking

• Lessons from failure

Brought to you by:

WorkOS—The modern API for auth and user identity

Orb—The flexible billing engine for modern pricing

Dovetail—Bring your customer into every decision

Find the transcript and references at: https://www.lennysnewsletter.com/p/kunal-shah-on-winning-in-india-second

Where to find Kunal Shah:

• X: https://twitter.com/kunalb11

• LinkedIn: https://www.linkedin.com/in/kunalshah1/

• Podcast: https://www.youtube.com/@CRED_club

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Kunal’s background

(04:22) The Delta 4 framework

(11:00) The success of Indian CEOs in the U.S.

(19:55) Challenges and opportunities in India

(23:04) DAUs vs. ARPU in Indian markets

(25:50) The perception of time in India

(27:55) The curse of focus in Asian markets

(30:33) Challenges and opportunities in India (continued)

(33:23) Lessons learned from building CRED

(36:40) Profit pools can provide valuable insights into the values of a country

(37:55) Founders’ role in company growth

(39:55) Profitability and Indian business culture

(43:24) Advice for staying positive amid criticism

(44:41) The promising market in India

(47:35) The power of curiosity

(52:59) Who Kunal looks up to

(55:31) Kunal’s favorite sources of content

(58:42) Asking great questions

(01:02:54) Contrarian corner: Wealth is nothing but storage of energy

(01:05:26) Failure corner

(01:08:57) Closing thoughts: Share your learnings

(01:09:38) Lightning round

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Emilie Gerber is the founder and CEO of Six Eastern, a top PR agency that’s worked with over 100 tech companies, from stealth startups to publicly traded companies. Before starting her own firm, she worked at Uber, where she led PR for the business development team and B2B programs. Prior to that, she worked at Box on product communications, with a focus on product launches and partnership announcements. In our conversation, we discuss:

• Why, and when, getting press is worth your time

• Common misconceptions about the impact press can have

• The second-order effects of press

• Which areas each publication (TechCrunch, Axios, The Verge, etc.) cares most about

• How to craft your pitch

• How to find and reach reporters

• How pitching press is different from pitching customers

• The effectiveness of direct communication through social media versus traditional press

Brought to you by:

Sprig—Build a product people love

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security.

Find the full transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-pr-emilie-gerber

Where to find Emilie Gerber:

• Substack: http://onbackgroundintel.substack.com

• LinkedIn: https://www.linkedin.com/in/emilie-gerber-59612230/

• Website: https://sixeastern.com/

• Email: hello@sixeastern.com

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Emilie’s background

(04:56) The value of press and second-order effects

(13:00) When press is not worth your time

(17:01) Different publications and their suitability

(25:36) Avoiding negative stories

(27:23) Finding aligned podcasts and awards

(31:12) Advice for reaching out to reporters

(37:23) Controversial pitches

(41:16) Avoiding category creation

(43:26) Examples of pitches that have worked well

(53:32) Pitching to Lenny

(55:46) Effective pitching strategies

(57:45) Improving pitch announcements

(01:03:01) Press releases

(01:07:06) Crafting a compelling story

(01:09:43) Traditional press vs. newsletters, podcasts, and social media

(01:15:50) Building a social media presence

(01:17:51) How to get a Morning Brew feature

(01:19:32) Advice on choosing a PR agency

(01:22:25) Timing and budget for PR

(01:25:39) Lightning round

Referenced:

• Perplexity: https://www.perplexity.ai/

• Who is Lenny Rachitsky? And what does he know that you don’t about making millions writing online?: https://www.fastcompany.com/90940453/lenny-rachitsky-newsletter-podcast-job-board-substack

• 42-year-old brings in an average of $41,000 a month from his podcast and works on it just 5 hours a week: https://www.cnbc.com/2024/01/11/lenny-rachitsky-podcast-brings-in-more-than-500k-a-year-heres-how.html

• How This Newsletter Writer Got More Than 300,000 Subscribers, and Now Makes “Significantly More” Than He Did at His Day Job: https://www.entrepreneur.com/starting-a-business/how-this-newsletter-writer-got-more-than-300000/447172

Business Insider: https://www.businessinsider.com/

• Contraline: https://www.contraline.com/

Forbes: https://www.forbes.com/

• TechCrunch: https://techcrunch.com/

• Axios: https://www.axios.com/

Fortune: https://fortune.com/

• Term Sheet: https://fortune.com/tag/term-sheet/

The Verge: https://www.theverge.com/

Wall Street Journal: https://www.wsj.com/

New York Times: https://www.nytimes.com/

• Found podcast: https://techcrunch.com/tag/found/

• Equity podcast: https://techcrunch.com/tag/equity-podcast/

• VentureBeat: https://venturebeat.com/

Fast Company: https://www.fastcompany.com/

• Clockwise: https://www.getclockwise.com

• Shopify deleted 322,000 hours of meetings. Should the rest of us be jealous?: https://www.npr.org/2023/02/15/1156804295/shopify-delete-meetings-zoom-virtual-productivity

• Shopify canceled all recurring meetings. Should you too?: https://www.getclockwise.com/blog/shopify-cancels-meetings

• Shopify’s new meeting cost calculator is well intentioned—but it’s not addressing the issue: https://www.fastcompany.com/90930137/shopifys-new-meeting-cost-calculator-is-well-intentioned-but-its-not-addressing-the-issue

• Matt Martin on LinkedIn: https://www.linkedin.com/in/voxmatt/

• Ramp: https://ramp.com/welcome

• Corporate card start-up Ramp targets Bill.com with free payments software: https://www.cnbc.com/2021/10/26/corporate-cards-ramp-targets-billcom-with-free-payments-software.html

• Bill: https://www.bill.com/

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

• Column Tax: https://www.columntax.com/

• Propel: https://www.joinpropel.com/

• Gamma: https://gamma.app/

• Gamma brings in $7M to bring the slide deck into the 21st century: https://techcrunch.com/2021/10/28/gamma-brings-in-7m-to-bring-the-slide-deck-into-the-21st-century/

• NewBank: https://www.newbankusa.com/

• Backed by a16z, Relay races to market with Zapier in its crosshairs: https://techcrunch.com/2023/10/11/relay-a16z-zapier-google/

• Zapier: https://zapier.com/

• Rajiv Ayyangar’s thread on X about tag lines: https://twitter.com/rajivayyangar/status/1758179077629100482

• Entropy: https://entropytechnologydesign.com/

• Money 20/20: https://www.money2020.com/

• Jim Bankoff on LinkedIn: https://www.linkedin.com/in/jimbankoff/

• Ramping Up: https://www.notboring.co/p/ramping-up

• Aaron Levie on LinkedIn: https://www.linkedin.com/in/boxaaron/

• Aaron Levie on X: https://twitter.com/levie

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Morning Brew: https://www.morningbrew.com/

• Tech Brew: https://www.emergingtechbrew.com/

• HR Brew: https://www.hr-brew.com/

• Mark Zuckerberg on Morning Brew Daily: https://www.youtube.com/watch?v=xQqsvRHjas4&t=1309s

How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225

The Walking Dead on Netflix: https://www.netflix.com/title/70177057

Yellowjackets on Paramount+: https://www.paramountplus.com/shows/yellowjackets/

The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Apple Vision Pro: https://www.apple.com/apple-vision-pro

• TNB Tech Minute: Startup Perplexity Challenges Google With AI Search: https://www.wsj.com/podcasts/tech-news-briefing/tnb-tech-minute-startup-perplexity-challenges-google-with-ai-search/984362d5-a8f0-48b4-8b55-ad7e570a74d2

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Emilie Gerber is the founder and CEO of Six Eastern, a top PR agency that’s worked with over 100 tech companies, from stealth startups to publicly traded companies. Before starting her own firm, she worked at Uber, where she led PR for the business development team and B2B programs. Prior to that, she worked at Box on product communications, with a focus on product launches and partnership announcements. In our conversation, we discuss:

• Why, and when, getting press is worth your time

• Common misconceptions about the impact press can have

• The second-order effects of press

• Which areas each publication (TechCrunch, Axios, The Verge, etc.) cares most about

• How to craft your pitch

• How to find and reach reporters

• How pitching press is different from pitching customers

• The effectiveness of direct communication through social media versus traditional press

Brought to you by:

Sprig—Build a product people love

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security.

Find the full transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-pr-emilie-gerber

Where to find Emilie Gerber:

• Substack: http://onbackgroundintel.substack.com

• LinkedIn: https://www.linkedin.com/in/emilie-gerber-59612230/

• Website: https://sixeastern.com/

• Email: hello@sixeastern.com

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Emilie’s background

(04:56) The value of press and second-order effects

(13:00) When press is not worth your time

(17:01) Different publications and their suitability

(25:36) Avoiding negative stories

(27:23) Finding aligned podcasts and awards

(31:12) Advice for reaching out to reporters

(37:23) Controversial pitches

(41:16) Avoiding category creation

(43:26) Examples of pitches that have worked well

(53:32) Pitching to Lenny

(55:46) Effective pitching strategies

(57:45) Improving pitch announcements

(01:03:01) Press releases

(01:07:06) Crafting a compelling story

(01:09:43) Traditional press vs. newsletters, podcasts, and social media

(01:15:50) Building a social media presence

(01:17:51) How to get a Morning Brew feature

(01:19:32) Advice on choosing a PR agency

(01:22:25) Timing and budget for PR

(01:25:39) Lightning round

Referenced:

• Perplexity: https://www.perplexity.ai/

• Who is Lenny Rachitsky? And what does he know that you don’t about making millions writing online?: https://www.fastcompany.com/90940453/lenny-rachitsky-newsletter-podcast-job-board-substack

• 42-year-old brings in an average of $41,000 a month from his podcast and works on it just 5 hours a week: https://www.cnbc.com/2024/01/11/lenny-rachitsky-podcast-brings-in-more-than-500k-a-year-heres-how.html

• How This Newsletter Writer Got More Than 300,000 Subscribers, and Now Makes “Significantly More” Than He Did at His Day Job: https://www.entrepreneur.com/starting-a-business/how-this-newsletter-writer-got-more-than-300000/447172

Business Insider: https://www.businessinsider.com/

• Contraline: https://www.contraline.com/

Forbes: https://www.forbes.com/

• TechCrunch: https://techcrunch.com/

• Axios: https://www.axios.com/

Fortune: https://fortune.com/

• Term Sheet: https://fortune.com/tag/term-sheet/

The Verge: https://www.theverge.com/

Wall Street Journal: https://www.wsj.com/

New York Times: https://www.nytimes.com/

• Found podcast: https://techcrunch.com/tag/found/

• Equity podcast: https://techcrunch.com/tag/equity-podcast/

• VentureBeat: https://venturebeat.com/

Fast Company: https://www.fastcompany.com/

• Clockwise: https://www.getclockwise.com

• Shopify deleted 322,000 hours of meetings. Should the rest of us be jealous?: https://www.npr.org/2023/02/15/1156804295/shopify-delete-meetings-zoom-virtual-productivity

• Shopify canceled all recurring meetings. Should you too?: https://www.getclockwise.com/blog/shopify-cancels-meetings

• Shopify’s new meeting cost calculator is well intentioned—but it’s not addressing the issue: https://www.fastcompany.com/90930137/shopifys-new-meeting-cost-calculator-is-well-intentioned-but-its-not-addressing-the-issue

• Matt Martin on LinkedIn: https://www.linkedin.com/in/voxmatt/

• Ramp: https://ramp.com/welcome

• Corporate card start-up Ramp targets Bill.com with free payments software: https://www.cnbc.com/2021/10/26/corporate-cards-ramp-targets-billcom-with-free-payments-software.html

• Bill: https://www.bill.com/

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

• Column Tax: https://www.columntax.com/

• Propel: https://www.joinpropel.com/

• Gamma: https://gamma.app/

• Gamma brings in $7M to bring the slide deck into the 21st century: https://techcrunch.com/2021/10/28/gamma-brings-in-7m-to-bring-the-slide-deck-into-the-21st-century/

• NewBank: https://www.newbankusa.com/

• Backed by a16z, Relay races to market with Zapier in its crosshairs: https://techcrunch.com/2023/10/11/relay-a16z-zapier-google/

• Zapier: https://zapier.com/

• Rajiv Ayyangar’s thread on X about tag lines: https://twitter.com/rajivayyangar/status/1758179077629100482

• Entropy: https://entropytechnologydesign.com/

• Money 20/20: https://www.money2020.com/

• Jim Bankoff on LinkedIn: https://www.linkedin.com/in/jimbankoff/

• Ramping Up: https://www.notboring.co/p/ramping-up

• Aaron Levie on LinkedIn: https://www.linkedin.com/in/boxaaron/

• Aaron Levie on X: https://twitter.com/levie

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Morning Brew: https://www.morningbrew.com/

• Tech Brew: https://www.emergingtechbrew.com/

• HR Brew: https://www.hr-brew.com/

• Mark Zuckerberg on Morning Brew Daily: https://www.youtube.com/watch?v=xQqsvRHjas4&t=1309s

How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225

The Walking Dead on Netflix: https://www.netflix.com/title/70177057

Yellowjackets on Paramount+: https://www.paramountplus.com/shows/yellowjackets/

The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Apple Vision Pro: https://www.apple.com/apple-vision-pro

• TNB Tech Minute: Startup Perplexity Challenges Google With AI Search: https://www.wsj.com/podcasts/tech-news-briefing/tnb-tech-minute-startup-perplexity-challenges-google-with-ai-search/984362d5-a8f0-48b4-8b55-ad7e570a74d2

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Noam Lovinsky has had a distinguished career in product, leaving an indelible mark at Facebook, YouTube, Thumbtack, and currently as the chief product officer at Grammarly. At Facebook, Noam helped establish the New Product Experimentation team; at Thumbtack, he was chief product officer; and at YouTube, he was one of the early product leaders overseeing the consumer experience. In our conversation, we discuss:

• Challenges and lessons from reviving growth at YouTube and Thumbtack

• Lessons from building Facebook’s New Product Experimentation team

• Insights into Grammarly’s success

• Knowing when it’s time to kill your project

• Why diversifying your growth channels is critical

• The power of visioning and storytelling in shaping product strategy

• How to create space for innovation at large companies

• The resilience and motivation of Grammarly’s team in Ukraine

Brought to you by:

Whimsical—The iterative product workspace

Vanta—Automate compliance. Simplify security.

LinkedIn Ads—Reach professionals and drive results for your business

Where to find Noam Lovinsky:

• X: https://twitter.com/noaml

• LinkedIn: https://www.linkedin.com/in/noaml/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Noam’s background

(04:18) Noam’s lack of online presence

(08:06) Lessons from YouTube: advocating for what’s best for yourself and the team

(14:31) Prioritizing what’s best for the business

(19:37) Knowing when it’s time to kill a project

(21:47) Lessons from Thumbtack: diversifying growth channels and overcoming challenges

(26:24) How Thumbtack turned growth around

(31:44) Building Airbnb’s instant booking feature

(35:28) Lessons from Thumbtack: team collaboration and product strategy

(38:38) Lessons from Facebook: building the New Product Experimentation team

(40:43) The importance of starting small and building community density

(46:07) Advice for building a startup within a startup

(48:52) Having an incentive system

(49:34) Lessons from Grammarly: adapting to changing user needs and building for the masses

(54:20) The scrappiness and profitability of Grammarly

(56:56) The resilience and motivation of the Grammarly team in Ukraine

(59:08) General career advice

(01:01:02) When to pull back

(01:02:58) Closing thoughts

(01:03:56) Lightning round

Referenced:

• Substack: https://substack.com/

• Hunter Walk on LinkedIn: https://www.linkedin.com/in/hunterwalk/

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/

• Salar Kamangar on LinkedIn: https://www.linkedin.com/in/salar-kamangar-5a059712/

• Grammarly: https://www.grammarly.com/

• Thumbtack: https://www.thumbtack.com/

• FRED on YouTube: https://www.youtube.com/FRED

• How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html

• Google+: https://en.wikipedia.org/wiki/Google%2B

• Marco Zappacosta on LinkedIn: https://www.linkedin.com/in/marcozappacosta/

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier/

• Whitney Steele on LinkedIn: https://www.linkedin.com/in/whitneydsteele/

• David Shein on LinkedIn: https://www.linkedin.com/in/davidshein/

• The magic of thinking big, by Lenny Rachitsky: https://www.mindtheproduct.com/the-magic-of-thinking-big-by-lenny-rachitsky/

• What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught

• New apps, new experiences: NPE Team, from Facebook: https://tech.facebook.com/engineering/2019/7/npe-team-from-facebook/

• The Origin Story of the BRC Trash Fence: https://journal.burningman.org/2016/05/black-rock-city/leaving-no-trace/the-origin-story-of-the-brc-trash-fence/

• Nike opens high-tech research and innovation lab: https://www.just-style.com/news/nike-opens-high-tech-research-and-innovation-lab/

• ChatGPT: https://chat.openai.com/

• Microsoft Copilot: https://copilot.microsoft.com/

• How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennyspodcast.com/how-to-grow-a-subscription-business-yuriy-timen-grammarly-canva-airtable/

• “The cave you fear to enter holds the treasure you seek”: https://gointothestory.blcklst.com/the-cave-you-fear-to-enter-holds-the-treasure-you-seek-d624e28c3848

Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

Fargo TV series on Hulu: https://www.fxnetworks.com/shows/fargo

• Arc browser: https://arc.net/

• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Noam Lovinsky has had a distinguished career in product, leaving an indelible mark at Facebook, YouTube, Thumbtack, and currently as the chief product officer at Grammarly. At Facebook, Noam helped establish the New Product Experimentation team; at Thumbtack, he was chief product officer; and at YouTube, he was one of the early product leaders overseeing the consumer experience. In our conversation, we discuss:

• Challenges and lessons from reviving growth at YouTube and Thumbtack

• Lessons from building Facebook’s New Product Experimentation team

• Insights into Grammarly’s success

• Knowing when it’s time to kill your project

• Why diversifying your growth channels is critical

• The power of visioning and storytelling in shaping product strategy

• How to create space for innovation at large companies

• The resilience and motivation of Grammarly’s team in Ukraine

Brought to you by:

Whimsical—The iterative product workspace

Vanta—Automate compliance. Simplify security.

LinkedIn Ads—Reach professionals and drive results for your business

Where to find Noam Lovinsky:

• X: https://twitter.com/noaml

• LinkedIn: https://www.linkedin.com/in/noaml/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Noam’s background

(04:18) Noam’s lack of online presence

(08:06) Lessons from YouTube: advocating for what’s best for yourself and the team

(14:31) Prioritizing what’s best for the business

(19:37) Knowing when it’s time to kill a project

(21:47) Lessons from Thumbtack: diversifying growth channels and overcoming challenges

(26:24) How Thumbtack turned growth around

(31:44) Building Airbnb’s instant booking feature

(35:28) Lessons from Thumbtack: team collaboration and product strategy

(38:38) Lessons from Facebook: building the New Product Experimentation team

(40:43) The importance of starting small and building community density

(46:07) Advice for building a startup within a startup

(48:52) Having an incentive system

(49:34) Lessons from Grammarly: adapting to changing user needs and building for the masses

(54:20) The scrappiness and profitability of Grammarly

(56:56) The resilience and motivation of the Grammarly team in Ukraine

(59:08) General career advice

(01:01:02) When to pull back

(01:02:58) Closing thoughts

(01:03:56) Lightning round

Referenced:

• Substack: https://substack.com/

• Hunter Walk on LinkedIn: https://www.linkedin.com/in/hunterwalk/

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/

• Salar Kamangar on LinkedIn: https://www.linkedin.com/in/salar-kamangar-5a059712/

• Grammarly: https://www.grammarly.com/

• Thumbtack: https://www.thumbtack.com/

• FRED on YouTube: https://www.youtube.com/FRED

• How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html

• Google+: https://en.wikipedia.org/wiki/Google%2B

• Marco Zappacosta on LinkedIn: https://www.linkedin.com/in/marcozappacosta/

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier/

• Whitney Steele on LinkedIn: https://www.linkedin.com/in/whitneydsteele/

• David Shein on LinkedIn: https://www.linkedin.com/in/davidshein/

• The magic of thinking big, by Lenny Rachitsky: https://www.mindtheproduct.com/the-magic-of-thinking-big-by-lenny-rachitsky/

• What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught

• New apps, new experiences: NPE Team, from Facebook: https://tech.facebook.com/engineering/2019/7/npe-team-from-facebook/

• The Origin Story of the BRC Trash Fence: https://journal.burningman.org/2016/05/black-rock-city/leaving-no-trace/the-origin-story-of-the-brc-trash-fence/

• Nike opens high-tech research and innovation lab: https://www.just-style.com/news/nike-opens-high-tech-research-and-innovation-lab/

• ChatGPT: https://chat.openai.com/

• Microsoft Copilot: https://copilot.microsoft.com/

• How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennyspodcast.com/how-to-grow-a-subscription-business-yuriy-timen-grammarly-canva-airtable/

• “The cave you fear to enter holds the treasure you seek”: https://gointothestory.blcklst.com/the-cave-you-fear-to-enter-holds-the-treasure-you-seek-d624e28c3848

Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

Fargo TV series on Hulu: https://www.fxnetworks.com/shows/fargo

• Arc browser: https://arc.net/

• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Marty Cagan is a luminary in the world of product. He’s the author of two of the most foundational books for product teams and product leaders (Inspired and Empowered), he’s the founder of Silicon Valley Product Group (one of the longest-running product advisory groups), and he’s almost certainly worked with more product leaders and teams than any human alive. Now he’s releasing his newest book, Transformed, which is sure to become a staple of tech-powered companies worldwide. Marty’s previous appearance on our show remains one of the most popular episodes to date. In this conversation, we discuss:

• The rise of “product management theater”

• Changes in the PM role post-ZIRP and the shift from growth to build functions

• The disconnect between good product companies and online product advice

• How over-hiring has created challenges in the product industry

• The most important skills for PMs to build

• How to know if you’re on a “feature team”

• The potential disruption of product management by AI

• Marty’s new book, Transformed: Moving to the Product Operating Model

• Four new competencies required for successful product organizations

Brought to you by:

Sprig—Build a product people love

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security.

Find the full transcript at: https://www.lennysnewsletter.com/p/product-management-theater-marty

Where to find Marty Cagan:

• X: https://twitter.com/cagan

• LinkedIn: https://www.linkedin.com/in/cagan/

• Silicon Valley Product Group: https://www.svpg.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Marty’s background

(04:46) His take on the state of product management

(12:08) Product management theater

(18:33) Feature teams vs. empowered product teams

(24:48) Skills of a real product manager

(29:27) The product management reckoning is here

(32:05) Taking control of your product management career

(34:59) The challenge of finding reliable product management advice

(40:18) The disconnect between good product companies and the product management community

(44:23) Top-down vs. bottom-up cultures

(47:06) The shift in product management post-ZIRP era

(49:44) The changing landscape of product management

(52:05) The disruption of PM skills by AI

(55:56) The purpose and content of Marty’s new book, Transformed

(01:02:05) The product operating model

(01:08:27) New competencies required for successful product teams

(01:11:25) Marty’s thoughts on product ops

(01:15:13) Advice for founders who don’t want product managers

(01:18:06) Lightning round

Referenced:

Transformed: Moving to the Product Operating Model: https://www.amazon.com/Transformed-Becoming-Product-Driven-Company-Silicon/dp/1119697336

Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

Empowered: Ordinary People, Extraordinary Products: https://www.amazon.com/EMPOWERED-Ordinary-Extraordinary-Products-Silicon/dp/111969129X

• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/

• Product Leadership Theater: https://www.svpg.com/product-leadership-theater/

• Product Management Theater: https://www.svpg.com/product-management-theater/

• Linear: https://linear.app/

• How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Mamas, don’t let your babies grow up to be coders, Jensen Huang warns: https://www.theregister.com/2024/02/27/jensen_huang_coders/

• Epic Waste: https://www.svpg.com/epic-waste/

• What is scrum and how to get started: https://www.atlassian.com/agile/scrum

• CSPO: https://www.scrumalliance.org/get-certified/product-owner-track/certified-scrum-product-owner

• PSPO: https://www.scrum.org/courses/professional-scrum-product-owner-training

• Jira: https://www.atlassian.com/software/jira

Continuous Discovery Habits: Discover Products That Create Customer Value and Business Value: https://www.amazon.com/Continuous-Discovery-Habits-Discover-Products/dp/1736633309

• Shreyas Doshi on LinkedIn: https://www.linkedin.com/in/shreyasdoshi/

• Ben Erez’s LinkedIn post: https://www.linkedin.com/feed/update/urn:li:activity:7168978777966891008/

• Oracle: https://www.oracle.com/

• The essence of product management | Christian Idiodi (SVPG): https://www.lennyspodcast.com/the-essence-of-product-management-christian-idiodi-svpg/

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennyspodcast.com/making-meta-andrew-boz-bosworth-cto/

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

• Partners at SVPG: https://www.svpg.com/team/

• Trainline: https://www.thetrainline.com/

• Almosafer: https://global.almosafer.com/

• Expedia: https://www.expedia.com/

• Shopify: https://www.shopify.com/

• Salesforce: https://www.salesforce.com/

• The ultimate guide to product operations | Melissa Perri and Denise Tilles: https://www.lennyspodcast.com/the-ultimate-guide-to-product-operations-melissa-perri-and-denise-tilles/

• Understanding the role of product ops | Christine Itwaru (Pendo): https://www.lennyspodcast.com/understanding-the-role-of-product-ops-christine-itwaru-pendo/

Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

What’s Our Problem?: A Self-Help Book for Societies: https://www.amazon.com/Whats-Our-Problem-Self-Help-Societies/dp/B0BVGH6T1Q

• Rivian: https://rivian.com/

• AI-1 airbag vest: https://www.klim.com/Ai-1-Airbag-Vest-3046-000

• Leslie Lamport’s quote: https://quotefancy.com/quote/3702194/Leslie-Lamport-If-you-re-thinking-without-writing-you-only-think-you-re-thinking

• Joan Didion’s quote: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Marty Cagan is a luminary in the world of product. He’s the author of two of the most foundational books for product teams and product leaders (Inspired and Empowered), he’s the founder of Silicon Valley Product Group (one of the longest-running product advisory groups), and he’s almost certainly worked with more product leaders and teams than any human alive. Now he’s releasing his newest book, Transformed, which is sure to become a staple of tech-powered companies worldwide. Marty’s previous appearance on our show remains one of the most popular episodes to date. In this conversation, we discuss:

• The rise of “product management theater”

• Changes in the PM role post-ZIRP and the shift from growth to build functions

• The disconnect between good product companies and online product advice

• How over-hiring has created challenges in the product industry

• The most important skills for PMs to build

• How to know if you’re on a “feature team”

• The potential disruption of product management by AI

• Marty’s new book, Transformed: Moving to the Product Operating Model

• Four new competencies required for successful product organizations

Brought to you by:

Sprig—Build a product people love

Eppo—Run reliable, impactful experiments

Vanta—Automate compliance. Simplify security.

Find the full transcript at: https://www.lennysnewsletter.com/p/product-management-theater-marty

Where to find Marty Cagan:

• X: https://twitter.com/cagan

• LinkedIn: https://www.linkedin.com/in/cagan/

• Silicon Valley Product Group: https://www.svpg.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Marty’s background

(04:46) His take on the state of product management

(12:08) Product management theater

(18:33) Feature teams vs. empowered product teams

(24:48) Skills of a real product manager

(29:27) The product management reckoning is here

(32:05) Taking control of your product management career

(34:59) The challenge of finding reliable product management advice

(40:18) The disconnect between good product companies and the product management community

(44:23) Top-down vs. bottom-up cultures

(47:06) The shift in product management post-ZIRP era

(49:44) The changing landscape of product management

(52:05) The disruption of PM skills by AI

(55:56) The purpose and content of Marty’s new book, Transformed

(01:02:05) The product operating model

(01:08:27) New competencies required for successful product teams

(01:11:25) Marty’s thoughts on product ops

(01:15:13) Advice for founders who don’t want product managers

(01:18:06) Lightning round

Referenced:

Transformed: Moving to the Product Operating Model: https://www.amazon.com/Transformed-Becoming-Product-Driven-Company-Silicon/dp/1119697336

Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

Empowered: Ordinary People, Extraordinary Products: https://www.amazon.com/EMPOWERED-Ordinary-Extraordinary-Products-Silicon/dp/111969129X

• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/

• Product Leadership Theater: https://www.svpg.com/product-leadership-theater/

• Product Management Theater: https://www.svpg.com/product-management-theater/

• Linear: https://linear.app/

• How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Mamas, don’t let your babies grow up to be coders, Jensen Huang warns: https://www.theregister.com/2024/02/27/jensen_huang_coders/

• Epic Waste: https://www.svpg.com/epic-waste/

• What is scrum and how to get started: https://www.atlassian.com/agile/scrum

• CSPO: https://www.scrumalliance.org/get-certified/product-owner-track/certified-scrum-product-owner

• PSPO: https://www.scrum.org/courses/professional-scrum-product-owner-training

• Jira: https://www.atlassian.com/software/jira

Continuous Discovery Habits: Discover Products That Create Customer Value and Business Value: https://www.amazon.com/Continuous-Discovery-Habits-Discover-Products/dp/1736633309

• Shreyas Doshi on LinkedIn: https://www.linkedin.com/in/shreyasdoshi/

• Ben Erez’s LinkedIn post: https://www.linkedin.com/feed/update/urn:li:activity:7168978777966891008/

• Oracle: https://www.oracle.com/

• The essence of product management | Christian Idiodi (SVPG): https://www.lennyspodcast.com/the-essence-of-product-management-christian-idiodi-svpg/

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennyspodcast.com/making-meta-andrew-boz-bosworth-cto/

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

• Partners at SVPG: https://www.svpg.com/team/

• Trainline: https://www.thetrainline.com/

• Almosafer: https://global.almosafer.com/

• Expedia: https://www.expedia.com/

• Shopify: https://www.shopify.com/

• Salesforce: https://www.salesforce.com/

• The ultimate guide to product operations | Melissa Perri and Denise Tilles: https://www.lennyspodcast.com/the-ultimate-guide-to-product-operations-melissa-perri-and-denise-tilles/

• Understanding the role of product ops | Christine Itwaru (Pendo): https://www.lennyspodcast.com/understanding-the-role-of-product-ops-christine-itwaru-pendo/

Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

What’s Our Problem?: A Self-Help Book for Societies: https://www.amazon.com/Whats-Our-Problem-Self-Help-Societies/dp/B0BVGH6T1Q

• Rivian: https://rivian.com/

• AI-1 airbag vest: https://www.klim.com/Ai-1-Airbag-Vest-3046-000

• Leslie Lamport’s quote: https://quotefancy.com/quote/3702194/Leslie-Lamport-If-you-re-thinking-without-writing-you-only-think-you-re-thinking

• Joan Didion’s quote: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ray (Jiayi) Cao is the global head of product strategy and operations for monetization product at TikTok. Prior to TikTok, Ray spent six years at Google helping scale Google Shopping globally. In our conversation, we discuss:

• TikTok’s internal culture and core values

• How TikTok’s product team operates

• How working at TikTok is different from working at Google

• How TikTok rolls out to new markets

• TikTok’s core principle of “context, not control”

• How their sales and product teams work together

• Lessons (and mistakes) from building TikTok’s early go-to-market team

• The importance of hiring for quality rather than quantity

• Insights on being successful on TikTok as a creator, a business, and an advertiser

Brought to you by:

WorkOS—The modern API for auth & user identity

Eppo—Run reliable, impactful experiments

OneSchema—Import CSV data 10x faster

Find the full transcript at: https://www.lennysnewsletter.com/p/inside-tiktok-culture-strategy-monetization

Where to find Ray Cao:

• LinkedIn: https://www.linkedin.com/in/jiayiraycao/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Ray’s background

(04:55) Cultural differences between Google and TikTok

(08:24) Fine-tuning the algorithm for different markets

(12:15) Examples of fine-tuning the algorithm

(15:11) Core principles and values of TikTok

(19:34) Hiring at TikTok

(21:38) Embracing the “always day one” mentality

(25:09) Collaboration between teams

(28:38) Amazon’s cultural influence

(31:14) Setting up the product organization for speed and innovation

(35:38) Building the go-to-market team

(40:18) What makes people successful at TikTok

(43:02) Thoughts on putting in long hours

(44:40) OKRs and planning at TikTok

(49:12) Tips for how to be successful on TikTok

(53:49) Tips for advertising on TikTok

(01:04:03) Getting started with TikTok Ads

(01:08:42) Common mistakes to avoid with TikTok advertising

(01:09:44) Ray’s favorite TikTok account

(01:10:54) Where to find Ray

Referenced:

• TikTok: https://tiktok.com/

• Google Shopping: https://shopping.google.com/

• Eugene Wei’s blog: https://www.eugenewei.com/

• TikTok and the Sorting Hat: https://www.eugenewei.com/blog/2020/8/3/tiktok-and-the-sorting-hat

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennyspodcast.com/how-netflix-builds-a-culture-of-excellence-elizabeth-stone-cto/

• Inside OpenAI | Logan Kilpatrick (head of developer relations): https://www.lennyspodcast.com/inside-openai-logan-kilpatrick-head-of-developer-relations/

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Lead with Context not Control: https://www.svpg.com/lead-with-context-not-control/

• Shuba on TikTok: https://www.tiktok.com/@tiktokbrownchick

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Duolingo leagues: https://duolingo.fandom.com/wiki/League

• CapCut: https://www.capcut.com/

• Amanda Talijan (silent baby item reviews) on TikTok: https://www.tiktok.com/@amanda_talijan/video/7321700482018233642

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Ray (Jiayi) Cao is the global head of product strategy and operations for monetization product at TikTok. Prior to TikTok, Ray spent six years at Google helping scale Google Shopping globally. In our conversation, we discuss:

• TikTok’s internal culture and core values

• How TikTok’s product team operates

• How working at TikTok is different from working at Google

• How TikTok rolls out to new markets

• TikTok’s core principle of “context, not control”

• How their sales and product teams work together

• Lessons (and mistakes) from building TikTok’s early go-to-market team

• The importance of hiring for quality rather than quantity

• Insights on being successful on TikTok as a creator, a business, and an advertiser

Brought to you by:

WorkOS—The modern API for auth & user identity

Eppo—Run reliable, impactful experiments

OneSchema—Import CSV data 10x faster

Find the full transcript at: https://www.lennysnewsletter.com/p/inside-tiktok-culture-strategy-monetization

Where to find Ray Cao:

• LinkedIn: https://www.linkedin.com/in/jiayiraycao/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Ray’s background

(04:55) Cultural differences between Google and TikTok

(08:24) Fine-tuning the algorithm for different markets

(12:15) Examples of fine-tuning the algorithm

(15:11) Core principles and values of TikTok

(19:34) Hiring at TikTok

(21:38) Embracing the “always day one” mentality

(25:09) Collaboration between teams

(28:38) Amazon’s cultural influence

(31:14) Setting up the product organization for speed and innovation

(35:38) Building the go-to-market team

(40:18) What makes people successful at TikTok

(43:02) Thoughts on putting in long hours

(44:40) OKRs and planning at TikTok

(49:12) Tips for how to be successful on TikTok

(53:49) Tips for advertising on TikTok

(01:04:03) Getting started with TikTok Ads

(01:08:42) Common mistakes to avoid with TikTok advertising

(01:09:44) Ray’s favorite TikTok account

(01:10:54) Where to find Ray

Referenced:

• TikTok: https://tiktok.com/

• Google Shopping: https://shopping.google.com/

• Eugene Wei’s blog: https://www.eugenewei.com/

• TikTok and the Sorting Hat: https://www.eugenewei.com/blog/2020/8/3/tiktok-and-the-sorting-hat

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennyspodcast.com/how-netflix-builds-a-culture-of-excellence-elizabeth-stone-cto/

• Inside OpenAI | Logan Kilpatrick (head of developer relations): https://www.lennyspodcast.com/inside-openai-logan-kilpatrick-head-of-developer-relations/

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Lead with Context not Control: https://www.svpg.com/lead-with-context-not-control/

• Shuba on TikTok: https://www.tiktok.com/@tiktokbrownchick

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Duolingo leagues: https://duolingo.fandom.com/wiki/League

• CapCut: https://www.capcut.com/

• Amanda Talijan (silent baby item reviews) on TikTok: https://www.tiktok.com/@amanda_talijan/video/7321700482018233642

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
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Published 2024-03-03

Making Meta | Andrew ‘Boz’ Bosworth (CTO)

102 min Transcript
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Andrew Bosworth—or Boz, as most people know him—is the chief technology officer at Meta and head of Reality Labs, the company’s augmented reality/virtual reality (AR/VR) organization, which he created in 2017. Boz joined Facebook in 2006 as their approximately 10th engineer, and in his 18-year tenure he built the original News Feed, Messenger, and Groups, as well as many early anti-abuse and infrastructure systems. At various times he has been the engineering director overseeing Events, Places, Photos, Videos, Timeline, Privacy, and more. Before Reality Labs, he ran the Ads and Business Platform product group, where he led engineering, product, research, analytics, and design, taking annual revenue from $4 billion to $40 billion in five years. Andrew currently leads Meta’s efforts in AR, VR, AI, and consumer hardware across Quest, Ray-Ban Meta glasses, and more. In our conversation, we discuss:

• Stories from the early days of Facebook

• Lessons from Meta’s downturn and recent turnaround

• Meta’s culture of transparency

• Boz’s thoughts on the Apple Vision Pro

• Why communication is the job

• Why you should regularly seek help from your manager

• Lessons in setting incentives and avoiding their misuse

• Why you should optimize for a variety in experience in your career

• The importance of trusting your own expertise and not being swayed by external opinions

• Stories of failures and personal growth

Brought to you by:

Vanta—Automate compliance. Simplify security.

Eppo—Run reliable, impactful experiments

Explo—Embed customer-facing analytics in your product

Find the full transcript at: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

Where to find Andrew Bosworth:

• Facebook: https://www.facebook.com/boz/

• Instagram: https://www.instagram.com/boztank/

• X: https://twitter.com/boztank

• LinkedIn: https://www.linkedin.com/in/andrew-bosworth-8247a01/

• Website: https://boz.com/

• Photography website: https://wardenshortbow.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Boz’s background

(04:48) Fun facts about him

(07:20) Early days at Facebook

(11:11) Advice for founders

(13:22) Leveraging leaders

(19:27) Tips for communicating with managers

(22:10) Transparency at Meta

(27:01) The importance of clear guidelines

(29:11) Involvement in the details

(33:15) Building the News Feed

(37:28) Passion and career growth

(40:25) Exploring new opportunities

(42:02) The value of variety in experience

(45:01) Giving and receiving feedback

(47:38) Boz’s tattoos

(51:30) Communication is the job

(01:00:47) Comparing VR headsets: Meta Quest 3 and Apple Vision Pro

(01:10:41) Meta’s downturn and turnaround

(01:16:10) Navigating org changes

(01:20:43) Lessons from failure

(01:26:33) Closing thoughts

(01:29:57) Lightning round

Referenced:

• Reality Labs: https://about.meta.com/realitylabs/

• Quest: https://www.meta.com/quest/

• Ray-Ban Meta smart glasses: https://www.ray-ban.com/usa/ray-ban-meta-smart-glasses

• Taekwondo: https://en.wikipedia.org/wiki/Taekwondo

• 4-H: https://4-h.org/

• David Copperfield’s website: https://www.davidcopperfield.com/html/

• MC Hammer on Instagram: https://www.instagram.com/mchammer/

• George W. Bush: https://www.whitehouse.gov/about-the-white-house/presidents/george-w-bush/

• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics

• Association for Computing Machinery: https://www.acm.org

• Get It Done: https://boz.com/articles/get-it-done

• Patrick Stewart on X: https://twitter.com/sirpatstew

• The FB Exec Practice That Changed the Way I Lead (about HPMs): https://livingos.substack.com/p/fb-exec-hpm

• Mark Zuckerberg on Facebook: https://www.facebook.com/zuck

• Chris Cox on LinkedIn: https://www.linkedin.com/in/chris-cox-2896b841/

• Javier Olivan on LinkedIn: https://www.linkedin.com/in/javierolivan/

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Eye of Sauron: https://lotr.fandom.com/wiki/Eye_of_Sauron

• Ruchi Sanghvi on LinkedIn: https://www.linkedin.com/in/rsanghvi/

• Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-e-schmidt/

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Best Advice Sheryl Sandberg Received: If Offered a Seat on Rocket Ship, Get On: https://news.yahoo.com/blogs/newsmakers/best-advice-sheryl-sandberg-received-don-t-idiot-161459450.html

• Veritas: https://en.wikipedia.org/wiki/Veritas

• Communication is The Job: https://boz.com/articles/communication-is-the-job

• Repetition does not spoil the prayer: https://www.linkedin.com/pulse/repetition-does-spoil-prayer-constantine-constantinides-m-d-ph-d--1f/

• Janet Lansbury’s website: https://www.janetlansbury.com/

• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

• Boz to the Future Episode 18: The Future According to Matthew Ball: https://www.meta.com/blog/quest/boz-to-the-future-episode-18-matthew-ball-metaverse-epyllion/

• Apple Vision Pro: https://www.apple.com/apple-vision-pro

• Quest 3 headset: https://www.meta.com/quest/quest-3/

• Virtual desktop: https://www.meta.com/experiences/2017050365004772/

• Meta Horizon Workrooms: https://www.meta.com/experiences/2514011888645651/ 

• After trying the Vision Pro, Mark Zuckerberg says Quest 3 ‘is the better product, period’: https://www.theverge.com/2024/2/13/24072413/mark-zuckerberg-apple-vision-pro-review-quest-3

• Lou Holtz on X: https://twitter.com/CoachLouHoltz88

• Gell-Mann amnesia effect: https://en.wiktionary.org/wiki/Gell-Mann_Amnesia_effect

• “Wet streets cause rain”: https://news.ycombinator.com/item?id=19026568

• Michael Crichton on X: https://twitter.com/CrichtonBooks

• AI research at Meta: https://ai.meta.com/research/

• Llama 2: https://llama.meta.com/

• Warren Buffett quote: https://www.brainyquote.com/quotes/warren_buffett_383933

• Mark Slee on LinkedIn: https://www.linkedin.com/in/mcslee/

• Dave Fetterman on LinkedIn: https://www.linkedin.com/in/davefetterman/

• Emacs and Vim: https://dev.to/george_udonte/emacs-and-vim-an-overview-for-beginners-2e65

• Ami Vora on LinkedIn: https://www.linkedin.com/in/amvora/

The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119

• Alan Turing: https://en.wikipedia.org/wiki/Alan_Turing

Good Inside: A Guide to Becoming the Parent You Want to Be: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/B09Y4WG7RJ

• Dr. Becky’s website: https://www.goodinside.com/

The Mandalorian on Disney+: https://www.disneyplus.com/series/the-mandalorian/3jLIGMDYINqD

• Scott Trowbridge on LinkedIn: https://www.linkedin.com/in/scott-trowbridge-b70866/

• Dave Filoni on X:  https://twitter.com/dave_filoni

• Jon Favreau on X: https://twitter.com/jon_favreau

• Mercedes-Benz AMG EQS Sedan: https://www.mbusa.com/en/vehicles/model/eqs/sedan/amgeqsv4

• Tracey Emin “Trust Yourself”: https://www.artsy.net/artwork/tracey-emin-trust-yourself

• Tracey Emin on Instagram: https://www.instagram.com/traceyeminstudio

• Rick Rubin: Protocols to Access Creative Energy and Process | Huberman Lab Podcast: https://www.youtube.com/watch?v=GpgqXCkRO-w

• Ansel Adams: https://en.wikipedia.org/wiki/Ansel_Adams

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Andrew Bosworth—or Boz, as most people know him—is the chief technology officer at Meta and head of Reality Labs, the company’s augmented reality/virtual reality (AR/VR) organization, which he created in 2017. Boz joined Facebook in 2006 as their approximately 10th engineer, and in his 18-year tenure he built the original News Feed, Messenger, and Groups, as well as many early anti-abuse and infrastructure systems. At various times he has been the engineering director overseeing Events, Places, Photos, Videos, Timeline, Privacy, and more. Before Reality Labs, he ran the Ads and Business Platform product group, where he led engineering, product, research, analytics, and design, taking annual revenue from $4 billion to $40 billion in five years. Andrew currently leads Meta’s efforts in AR, VR, AI, and consumer hardware across Quest, Ray-Ban Meta glasses, and more. In our conversation, we discuss:

• Stories from the early days of Facebook

• Lessons from Meta’s downturn and recent turnaround

• Meta’s culture of transparency

• Boz’s thoughts on the Apple Vision Pro

• Why communication is the job

• Why you should regularly seek help from your manager

• Lessons in setting incentives and avoiding their misuse

• Why you should optimize for a variety in experience in your career

• The importance of trusting your own expertise and not being swayed by external opinions

• Stories of failures and personal growth

Brought to you by:

Vanta—Automate compliance. Simplify security.

Eppo—Run reliable, impactful experiments

Explo—Embed customer-facing analytics in your product

Find the full transcript at: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

Where to find Andrew Bosworth:

• Facebook: https://www.facebook.com/boz/

• Instagram: https://www.instagram.com/boztank/

• X: https://twitter.com/boztank

• LinkedIn: https://www.linkedin.com/in/andrew-bosworth-8247a01/

• Website: https://boz.com/

• Photography website: https://wardenshortbow.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Boz’s background

(04:48) Fun facts about him

(07:20) Early days at Facebook

(11:11) Advice for founders

(13:22) Leveraging leaders

(19:27) Tips for communicating with managers

(22:10) Transparency at Meta

(27:01) The importance of clear guidelines

(29:11) Involvement in the details

(33:15) Building the News Feed

(37:28) Passion and career growth

(40:25) Exploring new opportunities

(42:02) The value of variety in experience

(45:01) Giving and receiving feedback

(47:38) Boz’s tattoos

(51:30) Communication is the job

(01:00:47) Comparing VR headsets: Meta Quest 3 and Apple Vision Pro

(01:10:41) Meta’s downturn and turnaround

(01:16:10) Navigating org changes

(01:20:43) Lessons from failure

(01:26:33) Closing thoughts

(01:29:57) Lightning round

Referenced:

• Reality Labs: https://about.meta.com/realitylabs/

• Quest: https://www.meta.com/quest/

• Ray-Ban Meta smart glasses: https://www.ray-ban.com/usa/ray-ban-meta-smart-glasses

• Taekwondo: https://en.wikipedia.org/wiki/Taekwondo

• 4-H: https://4-h.org/

• David Copperfield’s website: https://www.davidcopperfield.com/html/

• MC Hammer on Instagram: https://www.instagram.com/mchammer/

• George W. Bush: https://www.whitehouse.gov/about-the-white-house/presidents/george-w-bush/

• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics

• Association for Computing Machinery: https://www.acm.org

• Get It Done: https://boz.com/articles/get-it-done

• Patrick Stewart on X: https://twitter.com/sirpatstew

• The FB Exec Practice That Changed the Way I Lead (about HPMs): https://livingos.substack.com/p/fb-exec-hpm

• Mark Zuckerberg on Facebook: https://www.facebook.com/zuck

• Chris Cox on LinkedIn: https://www.linkedin.com/in/chris-cox-2896b841/

• Javier Olivan on LinkedIn: https://www.linkedin.com/in/javierolivan/

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Eye of Sauron: https://lotr.fandom.com/wiki/Eye_of_Sauron

• Ruchi Sanghvi on LinkedIn: https://www.linkedin.com/in/rsanghvi/

• Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-e-schmidt/

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Best Advice Sheryl Sandberg Received: If Offered a Seat on Rocket Ship, Get On: https://news.yahoo.com/blogs/newsmakers/best-advice-sheryl-sandberg-received-don-t-idiot-161459450.html

• Veritas: https://en.wikipedia.org/wiki/Veritas

• Communication is The Job: https://boz.com/articles/communication-is-the-job

• Repetition does not spoil the prayer: https://www.linkedin.com/pulse/repetition-does-spoil-prayer-constantine-constantinides-m-d-ph-d--1f/

• Janet Lansbury’s website: https://www.janetlansbury.com/

• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

• Boz to the Future Episode 18: The Future According to Matthew Ball: https://www.meta.com/blog/quest/boz-to-the-future-episode-18-matthew-ball-metaverse-epyllion/

• Apple Vision Pro: https://www.apple.com/apple-vision-pro

• Quest 3 headset: https://www.meta.com/quest/quest-3/

• Virtual desktop: https://www.meta.com/experiences/2017050365004772/

• Meta Horizon Workrooms: https://www.meta.com/experiences/2514011888645651/ 

• After trying the Vision Pro, Mark Zuckerberg says Quest 3 ‘is the better product, period’: https://www.theverge.com/2024/2/13/24072413/mark-zuckerberg-apple-vision-pro-review-quest-3

• Lou Holtz on X: https://twitter.com/CoachLouHoltz88

• Gell-Mann amnesia effect: https://en.wiktionary.org/wiki/Gell-Mann_Amnesia_effect

• “Wet streets cause rain”: https://news.ycombinator.com/item?id=19026568

• Michael Crichton on X: https://twitter.com/CrichtonBooks

• AI research at Meta: https://ai.meta.com/research/

• Llama 2: https://llama.meta.com/

• Warren Buffett quote: https://www.brainyquote.com/quotes/warren_buffett_383933

• Mark Slee on LinkedIn: https://www.linkedin.com/in/mcslee/

• Dave Fetterman on LinkedIn: https://www.linkedin.com/in/davefetterman/

• Emacs and Vim: https://dev.to/george_udonte/emacs-and-vim-an-overview-for-beginners-2e65

• Ami Vora on LinkedIn: https://www.linkedin.com/in/amvora/

The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119

• Alan Turing: https://en.wikipedia.org/wiki/Alan_Turing

Good Inside: A Guide to Becoming the Parent You Want to Be: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/B09Y4WG7RJ

• Dr. Becky’s website: https://www.goodinside.com/

The Mandalorian on Disney+: https://www.disneyplus.com/series/the-mandalorian/3jLIGMDYINqD

• Scott Trowbridge on LinkedIn: https://www.linkedin.com/in/scott-trowbridge-b70866/

• Dave Filoni on X:  https://twitter.com/dave_filoni

• Jon Favreau on X: https://twitter.com/jon_favreau

• Mercedes-Benz AMG EQS Sedan: https://www.mbusa.com/en/vehicles/model/eqs/sedan/amgeqsv4

• Tracey Emin “Trust Yourself”: https://www.artsy.net/artwork/tracey-emin-trust-yourself

• Tracey Emin on Instagram: https://www.instagram.com/traceyeminstudio

• Rick Rubin: Protocols to Access Creative Energy and Process | Huberman Lab Podcast: https://www.youtube.com/watch?v=GpgqXCkRO-w

• Ansel Adams: https://en.wikipedia.org/wiki/Ansel_Adams

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Donna Lichaw is an internationally sought-after executive coach, keynote speaker, and best-selling author. She helps visionary founders, CEOs, and executive teams level up their leadership and scale their impact while staying true to their mission, purpose, and themselves. Donna works with leaders at companies like Google, Disney, Twitter, Microsoft, Mailchimp, and Adobe, as well as a plethora of mission-driven startups and nonprofits. In our conversation, we discuss:

• How our personal narratives influence our success and failure

• Why identifying your superpowers (and kryptonite) is so important, and how to do it

• The value of doubling down on your strengths rather than trying to fix weaknesses

• How to acknowledge and reframe feelings of impostor syndrome

• The Double Diamond framework for personal growth and goal-setting

• The power of visualization and how it can fuel motivation and creativity

Brought to you by:

OneSchema—Import CSV data 10x faster

Sendbird—The (all-in-one) communications API platform for mobile apps

Sprig—Build a product people love

Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-discover-your-superpowers

Where to find Donna Lichaw:

• LinkedIn: https://www.linkedin.com/in/dlichaw/

• Website: https://www.donnalichaw.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Donna’s background

(04:25) Donna’s origin story and transition to coaching

(08:38) The power of storytelling in leadership

(11:36) Becoming the hero of your own story

(14:49) Changing your story

(21:19) Understanding and shifting others’ stories

(25:41) Imposter syndrome

(31:28) Exploring different types of kryptonite

(36:41) Identifying and leveraging strengths

(43:53) Identifying superpowers

(56:39) Running experiments

(01:01:52) Using product frameworks for personal growth

(01:12:41) Identifying subconscious goals

(01:15:27) Envisioning impact

(01:16:44) Lightning round

Referenced:

The Leader’s Journey: Transforming Your Leadership to Achieve the Extraordinary: https://www.amazon.com/Leaders-Journey-Transforming-Leadership-Extraordinary/dp/1959029134

• Effective Leadership Is Transformational, by Ken Blanchard: https://www.chieflearningofficer.com/2019/06/13/effective-leadership-is-transformational/

• Ken Blanchard’s website: https://www.blanchard.com/

• How to write a kickass README: https://dev.to/scottydocs/how-to-write-a-kickass-readme-5af9

• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your Data Scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome

• Community Wisdom: Dealing with impostor syndrome as a PM: https://www.lennysnewsletter.com/p/community-wisdom-dealing-with-impostor

• Stuart Smalley: https://en.wikipedia.org/wiki/Stuart_Smalley

• Kryptonite: https://en.wikipedia.org/wiki/Kryptonite

• How Dyslexic Thinking Gives Entrepreneurs a Competitive Edge: https://www.forbes.com/sites/alisoncoleman/2023/05/16/how-dyslexic-thinking-gives-entrepreneurs-a-competitive-edge/

• Characterizing Creative Thinking and Creative Achievements in Relation to Symptoms of Attention-Deficit/Hyperactivity Disorder and Autism Spectrum Disorder: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9283685/

• Robert Iger: https://thewaltdisneycompany.com/leaders/robert-a-iger/

• CliftonStrengths test: https://www.gallup.com/cliftonstrengths/en/252137/home.aspx

• VIA Character Strengths: https://www.viacharacter.org/

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/

•10 Steve Jobs Quotes That’ll Stick With You Long After You Read Them: https://www.themuse.com/advice/10-steve-jobs-quotes-thatll-stick-with-you-long-after-you-read-them

• Gestalt coaching: https://gestaltcenterforcoaching.com/

• Gestalt therapy: https://www.psychologytoday.com/us/therapy-types/gestalt-therapy

• Head, Heart and Hands: http://creatingminds.org/tools/head_heart_hands.htm

• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennyspodcast.com/managing-nerves-anxiety-and-burnout-jonny-miller-nervous-system-mastery/

The User’s Journey: Storymapping Products That People Love: https://www.amazon.com/Users-Journey-Storymapping-Products-People/dp/1933820314

For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy

The Art of Possibility: Transforming Professional and Personal Life: https://www.amazon.com/Art-Possibility-Transforming-Professional-Personal/dp/0142001104

• IMPRESA Monkey Noodle Stretchy String Fidget/Sensory Toys: https://www.amazon.com/IMPRESA-Glitter-Stretchy-Phthalate-Latex-Free/dp/B0868X6NRQ

• Dolly Parton quote: https://www.goodreads.com/quotes/21268-find-out-who-you-are-and-do-it-on-purpose

• Donna’s favorite fidgets: https://pen-name.notion.site/Donna-Lichaw-s-Favorite-Fidgets-f84f241d31704a498d71d3502af1821b?pvs=4

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Donna Lichaw is an internationally sought-after executive coach, keynote speaker, and best-selling author. She helps visionary founders, CEOs, and executive teams level up their leadership and scale their impact while staying true to their mission, purpose, and themselves. Donna works with leaders at companies like Google, Disney, Twitter, Microsoft, Mailchimp, and Adobe, as well as a plethora of mission-driven startups and nonprofits. In our conversation, we discuss:

• How our personal narratives influence our success and failure

• Why identifying your superpowers (and kryptonite) is so important, and how to do it

• The value of doubling down on your strengths rather than trying to fix weaknesses

• How to acknowledge and reframe feelings of impostor syndrome

• The Double Diamond framework for personal growth and goal-setting

• The power of visualization and how it can fuel motivation and creativity

Brought to you by:

OneSchema—Import CSV data 10x faster

Sendbird—The (all-in-one) communications API platform for mobile apps

Sprig—Build a product people love

Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-discover-your-superpowers

Where to find Donna Lichaw:

• LinkedIn: https://www.linkedin.com/in/dlichaw/

• Website: https://www.donnalichaw.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Donna’s background

(04:25) Donna’s origin story and transition to coaching

(08:38) The power of storytelling in leadership

(11:36) Becoming the hero of your own story

(14:49) Changing your story

(21:19) Understanding and shifting others’ stories

(25:41) Imposter syndrome

(31:28) Exploring different types of kryptonite

(36:41) Identifying and leveraging strengths

(43:53) Identifying superpowers

(56:39) Running experiments

(01:01:52) Using product frameworks for personal growth

(01:12:41) Identifying subconscious goals

(01:15:27) Envisioning impact

(01:16:44) Lightning round

Referenced:

The Leader’s Journey: Transforming Your Leadership to Achieve the Extraordinary: https://www.amazon.com/Leaders-Journey-Transforming-Leadership-Extraordinary/dp/1959029134

• Effective Leadership Is Transformational, by Ken Blanchard: https://www.chieflearningofficer.com/2019/06/13/effective-leadership-is-transformational/

• Ken Blanchard’s website: https://www.blanchard.com/

• How to write a kickass README: https://dev.to/scottydocs/how-to-write-a-kickass-readme-5af9

• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your Data Scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome

• Community Wisdom: Dealing with impostor syndrome as a PM: https://www.lennysnewsletter.com/p/community-wisdom-dealing-with-impostor

• Stuart Smalley: https://en.wikipedia.org/wiki/Stuart_Smalley

• Kryptonite: https://en.wikipedia.org/wiki/Kryptonite

• How Dyslexic Thinking Gives Entrepreneurs a Competitive Edge: https://www.forbes.com/sites/alisoncoleman/2023/05/16/how-dyslexic-thinking-gives-entrepreneurs-a-competitive-edge/

• Characterizing Creative Thinking and Creative Achievements in Relation to Symptoms of Attention-Deficit/Hyperactivity Disorder and Autism Spectrum Disorder: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9283685/

• Robert Iger: https://thewaltdisneycompany.com/leaders/robert-a-iger/

• CliftonStrengths test: https://www.gallup.com/cliftonstrengths/en/252137/home.aspx

• VIA Character Strengths: https://www.viacharacter.org/

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/

•10 Steve Jobs Quotes That’ll Stick With You Long After You Read Them: https://www.themuse.com/advice/10-steve-jobs-quotes-thatll-stick-with-you-long-after-you-read-them

• Gestalt coaching: https://gestaltcenterforcoaching.com/

• Gestalt therapy: https://www.psychologytoday.com/us/therapy-types/gestalt-therapy

• Head, Heart and Hands: http://creatingminds.org/tools/head_heart_hands.htm

• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennyspodcast.com/managing-nerves-anxiety-and-burnout-jonny-miller-nervous-system-mastery/

The User’s Journey: Storymapping Products That People Love: https://www.amazon.com/Users-Journey-Storymapping-Products-People/dp/1933820314

For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy

The Art of Possibility: Transforming Professional and Personal Life: https://www.amazon.com/Art-Possibility-Transforming-Professional-Personal/dp/0142001104

• IMPRESA Monkey Noodle Stretchy String Fidget/Sensory Toys: https://www.amazon.com/IMPRESA-Glitter-Stretchy-Phthalate-Latex-Free/dp/B0868X6NRQ

• Dolly Parton quote: https://www.goodreads.com/quotes/21268-find-out-who-you-are-and-do-it-on-purpose

• Donna’s favorite fidgets: https://pen-name.notion.site/Donna-Lichaw-s-Favorite-Fidgets-f84f241d31704a498d71d3502af1821b?pvs=4

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Elizabeth Stone is the chief technology officer of Netflix. She previously served as vice president of product data science and engineering, and as vice president of data and insights, at Netflix. Before Netflix, Elizabeth was vice president of science at Lyft, chief operating officer at Nuna, a trader at Merrill Lynch, and an economist at Analysis Group. In our conversation, we discuss:

• Elizabeth’s advice for career advancement

• Netflix’s unique high-performance culture

• How, and why, Netflix maintains a high bar for excellence

• Intentional leadership practices

• How to foster an “open door” culture within your team

• The Keeper Test and how it contributes to maintaining a high bar for excellence

• The power of transparent communication

• Much more

Brought to you by:

Vanta—Automate compliance. Simplify security.

Sendbird—The (all-in-one) communications API platform for mobile apps

Explo—Embed customer-facing analytics in your product

Find the full transcript at: https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

Where to find Elizabeth Stone:

• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Elizabeth’s background

(04:36) Life as CTO vs. VP of Data

(05:57) The role of economists in tech companies

(08:32) Using economics to understand incentives

(10:07) Success and career growth

(20:15) Setting expectations

(25:02) Advice for how to avoid burnout

(27:44) Netflix culture: high talent density

(30:31) Netflix culture: candor and directness

(31:45) The Keeper Test

(39:01) Maintaining a high bar for excellence

(43:54) Netflix culture: freedom and responsibility

(46:18) Unconventional processes at Netflix

(47:55) Examples of candor

(51:44) Data and insights team structure

(01:00:12) Staying close to teams

(01:02:31) Advice on being present

(01:07:40) Lightning round

Referenced:

• What to Know About the Netflix Cup, Today’s First-Ever Live Sports Event: https://www.netflix.com/tudum/articles/netflix-cup-live-event-date-news

• Ann Miura Ko interview | The Tim Ferriss Show (Podcast): https://www.youtube.com/watch?v=h2GO0Ks_VGg

• Netflix culture: https://jobs.netflix.com/culture

No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860

• Reed Hastings on LinkedIn: https://www.linkedin.com/in/reedhastings/

• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it/

The Hunger Games: https://en.wikipedia.org/wiki/The_Hunger_Games

• Nan Yu on LinkedIn: https://www.linkedin.com/in/thenanyu/

• Work Life Philosophy: https://jobs.netflix.com/work-life-philosophy

• The Scoop: Netflix’s historic introduction of levels for software engineers: https://blog.pragmaticengineer.com/netflix-levels/

• Chaos Monkey: https://www.techtarget.com/whatis/definition/Chaos-Monkey

• Ali Rauh on LinkedIn: https://www.linkedin.com/in/ali-rauh/

• Keith Henwood on LinkedIn: https://www.linkedin.com/in/keith-henwood/

• Jeff Bezos’ Morning Routine of Puttering Around—How It Works: https://medium.com/illumination/jeff-bezos-morning-routine-of-puttering-around-how-it-works-9d73f359ac8d

What I Talk About When I Talk About Running: A Memoir: https://www.amazon.com/What-Talk-About-When-Running/dp/0307389839

A Fine Balance: https://www.amazon.com/Fine-Balance-Rohinton-Mistry/dp/140003065X

Triangle of Sadness on Hulu: https://www.hulu.com/movie/triangle-of-sadness-f60937bd-45f4-469a-938f-db95026953a1

Beef on Netflix: https://www.netflix.com/title/81447461

• Fellow pour-over coffee set: https://fellowproducts.com/products/stagg-xf-pour-over-set

• Peloton bikes: https://www.onepeloton.com/shop/bike

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Elizabeth Stone is the chief technology officer of Netflix. She previously served as vice president of product data science and engineering, and as vice president of data and insights, at Netflix. Before Netflix, Elizabeth was vice president of science at Lyft, chief operating officer at Nuna, a trader at Merrill Lynch, and an economist at Analysis Group. In our conversation, we discuss:

• Elizabeth’s advice for career advancement

• Netflix’s unique high-performance culture

• How, and why, Netflix maintains a high bar for excellence

• Intentional leadership practices

• How to foster an “open door” culture within your team

• The Keeper Test and how it contributes to maintaining a high bar for excellence

• The power of transparent communication

• Much more

Brought to you by:

Vanta—Automate compliance. Simplify security.

Sendbird—The (all-in-one) communications API platform for mobile apps

Explo—Embed customer-facing analytics in your product

Find the full transcript at: https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

Where to find Elizabeth Stone:

• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Elizabeth’s background

(04:36) Life as CTO vs. VP of Data

(05:57) The role of economists in tech companies

(08:32) Using economics to understand incentives

(10:07) Success and career growth

(20:15) Setting expectations

(25:02) Advice for how to avoid burnout

(27:44) Netflix culture: high talent density

(30:31) Netflix culture: candor and directness

(31:45) The Keeper Test

(39:01) Maintaining a high bar for excellence

(43:54) Netflix culture: freedom and responsibility

(46:18) Unconventional processes at Netflix

(47:55) Examples of candor

(51:44) Data and insights team structure

(01:00:12) Staying close to teams

(01:02:31) Advice on being present

(01:07:40) Lightning round

Referenced:

• What to Know About the Netflix Cup, Today’s First-Ever Live Sports Event: https://www.netflix.com/tudum/articles/netflix-cup-live-event-date-news

• Ann Miura Ko interview | The Tim Ferriss Show (Podcast): https://www.youtube.com/watch?v=h2GO0Ks_VGg

• Netflix culture: https://jobs.netflix.com/culture

No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860

• Reed Hastings on LinkedIn: https://www.linkedin.com/in/reedhastings/

• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it/

The Hunger Games: https://en.wikipedia.org/wiki/The_Hunger_Games

• Nan Yu on LinkedIn: https://www.linkedin.com/in/thenanyu/

• Work Life Philosophy: https://jobs.netflix.com/work-life-philosophy

• The Scoop: Netflix’s historic introduction of levels for software engineers: https://blog.pragmaticengineer.com/netflix-levels/

• Chaos Monkey: https://www.techtarget.com/whatis/definition/Chaos-Monkey

• Ali Rauh on LinkedIn: https://www.linkedin.com/in/ali-rauh/

• Keith Henwood on LinkedIn: https://www.linkedin.com/in/keith-henwood/

• Jeff Bezos’ Morning Routine of Puttering Around—How It Works: https://medium.com/illumination/jeff-bezos-morning-routine-of-puttering-around-how-it-works-9d73f359ac8d

What I Talk About When I Talk About Running: A Memoir: https://www.amazon.com/What-Talk-About-When-Running/dp/0307389839

A Fine Balance: https://www.amazon.com/Fine-Balance-Rohinton-Mistry/dp/140003065X

Triangle of Sadness on Hulu: https://www.hulu.com/movie/triangle-of-sadness-f60937bd-45f4-469a-938f-db95026953a1

Beef on Netflix: https://www.netflix.com/title/81447461

• Fellow pour-over coffee set: https://fellowproducts.com/products/stagg-xf-pour-over-set

• Peloton bikes: https://www.onepeloton.com/shop/bike

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Published 2024-02-18

Building a world-class sales org | Jason Lemkin (SaaStr)

121 min Transcript
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Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss:

• How far you should go without a salesperson

• Signs it’s time to hire salespeople

• Why you need to hire two salespeople

• How to compensate your salespeople

• How to interview salespeople

• When to hire a VP of Sales

• How to prevent their flaming out

• How to scale your sales org

• How to improve the relationship between your sales and product teams

• Much more

Brought to you by:

CommandBar—AI-powered user assistance for modern products and impatient users

Vanta—Automate compliance. Simplify security.

LinkedIn Ads—Reach professionals and drive results for your business

Find the full transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

Where to find Jason Lemkin:

• X: https://twitter.com/jasonlk

• LinkedIn: https://www.linkedin.com/in/jasonmlemkin/

• Website: https://www.saastr.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jason’s background

(06:18) The importance of sales in B2B businesses

(11:23) Signs that you should start hiring salespeople

(14:19) Attributes to look for in early sales reps

(19:08) Hiring a VP of Sales

(26:43) The role of a VP of Sales

(30:06) Interviewing salespeople

(45:16) Determining sales compensation and quota

(53:34) Transitioning from 100% commission to a smaller percentage

(56:58) Indicators of a hard-to-sell product

(59:39) Scaling the sales organization

(01:05:26) Understanding sales roles and titles

(01:10:02) Product involvement in sales, and vice versa

(01:20:32) Thoughts on product teams taking on P&L responsibilities

(01:27:23) One thing founders can do to become better at sales

(01:31:02) The ideal trial length for a free trial sales team

(01:39:50) Closing thoughts

(01:41:43) Lightning round

Referenced:

• Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/

• Snowflake: https://www.snowflake.com/en/

• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/

• Salesforce: https://www.salesforce.com/

• HubSpot: https://www.hubspot.com/

• Twilio: https://www.twilio.com/

• Cloudflare: https://www.cloudflare.com/

• GitHub: https://github.com/

Columbo: https://www.imdb.com/title/tt1466074/

• What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti

• Adobe: https://www.adobe.com/

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/

• Pipedrive: https://www.pipedrive.com/

• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/

• Gong: https://www.gong.io/

• Zendesk: https://www.zendesk.com/

• ZoomInfo: https://www.zoominfo.com/

• Apollo: https://www.apollo.io/

• Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/

• SAP: https://www.sap.com/

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• VistaPrint: https://www.vistaprint.com/

• Procore: https://www.procore.com/

• Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/

• Wordpress: https://wordpress.com/

• SaaStr University: https://app.saastruniversity.com/collections/20252

From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691

• Pavilion: https://www.joinpavilion.com/

• Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw

The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK

Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick

• OpusClip app: https://www.opus.pro/

• OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/

• SaaStr conferences: https://www.saastr.com/events/

• Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html

• Zoomtopia: https://zoomtopia.com/

• Money20/20: https://us.money2020.com/

• Shoptalk: https://shoptalk.com/

• Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/

• Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss:

• How far you should go without a salesperson

• Signs it’s time to hire salespeople

• Why you need to hire two salespeople

• How to compensate your salespeople

• How to interview salespeople

• When to hire a VP of Sales

• How to prevent their flaming out

• How to scale your sales org

• How to improve the relationship between your sales and product teams

• Much more

Brought to you by:

CommandBar—AI-powered user assistance for modern products and impatient users

Vanta—Automate compliance. Simplify security.

LinkedIn Ads—Reach professionals and drive results for your business

Find the full transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

Where to find Jason Lemkin:

• X: https://twitter.com/jasonlk

• LinkedIn: https://www.linkedin.com/in/jasonmlemkin/

• Website: https://www.saastr.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Jason’s background

(06:18) The importance of sales in B2B businesses

(11:23) Signs that you should start hiring salespeople

(14:19) Attributes to look for in early sales reps

(19:08) Hiring a VP of Sales

(26:43) The role of a VP of Sales

(30:06) Interviewing salespeople

(45:16) Determining sales compensation and quota

(53:34) Transitioning from 100% commission to a smaller percentage

(56:58) Indicators of a hard-to-sell product

(59:39) Scaling the sales organization

(01:05:26) Understanding sales roles and titles

(01:10:02) Product involvement in sales, and vice versa

(01:20:32) Thoughts on product teams taking on P&L responsibilities

(01:27:23) One thing founders can do to become better at sales

(01:31:02) The ideal trial length for a free trial sales team

(01:39:50) Closing thoughts

(01:41:43) Lightning round

Referenced:

• Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/

• Snowflake: https://www.snowflake.com/en/

• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/

• Salesforce: https://www.salesforce.com/

• HubSpot: https://www.hubspot.com/

• Twilio: https://www.twilio.com/

• Cloudflare: https://www.cloudflare.com/

• GitHub: https://github.com/

Columbo: https://www.imdb.com/title/tt1466074/

• What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti

• Adobe: https://www.adobe.com/

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/

• Pipedrive: https://www.pipedrive.com/

• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/

• Gong: https://www.gong.io/

• Zendesk: https://www.zendesk.com/

• ZoomInfo: https://www.zoominfo.com/

• Apollo: https://www.apollo.io/

• Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/

• SAP: https://www.sap.com/

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

• VistaPrint: https://www.vistaprint.com/

• Procore: https://www.procore.com/

• Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/

• Wordpress: https://wordpress.com/

• SaaStr University: https://app.saastruniversity.com/collections/20252

From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691

• Pavilion: https://www.joinpavilion.com/

• Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw

The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK

Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick

• OpusClip app: https://www.opus.pro/

• OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/

• SaaStr conferences: https://www.saastr.com/events/

• Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html

• Zoomtopia: https://zoomtopia.com/

• Money20/20: https://us.money2020.com/

• Shoptalk: https://shoptalk.com/

• Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/

• Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jake Knapp and John Zeratsky are the authors of best-selling books Sprint and Make Time. They have helped more than 300 teams design new products and bring them to market, including those at YouTube, Gusto, One Medical Group, and Slack. Jake and John are co-founders of the venture capital firm Character, where they support startups with capital and sprints. Previously, they were operating partners at Google Ventures and, before that, design leaders at Google, where John worked on Google Ads and YouTube and Jake helped build Gmail and co-founded Google Meet. In our conversation, we discuss:

• “Busy bandwagon” and “infinity pools”

• Creating one “highlight” each day

• Their four-part framework for productivity

• How to use the calendar to design your day

• How creating friction can help you avoid distractions

• Tips on creating a distraction-free phone

• Strategies for managing email and distractions

• The importance of reflecting on the day and making time for meaningful work

• Design sprints

Brought to you by:

Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

Whimsical—The iterative product workspace

WorkOS—The modern API for auth and user identity

Find the full transcript at: https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake

Where to find Jake Knapp:

• X: https://twitter.com/jakek

• LinkedIn: https://www.linkedin.com/in/jake-knapp/

• Website: https://jakeknapp.com/

Where to find John Zeratsky:

• X: https://twitter.com/jazer

• LinkedIn: https://www.linkedin.com/in/johnzeratsky/

• Website: https://johnzeratsky.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) About Jake and John

(04:10) Recording the audiobook for Make Time

(06:06) What people often get wrong when trying to become more productive

(11:24) The busy bandwagon and infinity pools

(15:22) Real talk: Jake and John’s productivity levels

(20:10) The four-part framework for getting more done: Highlight, Laser, Energize, Reflect

(25:15) Step 1: Highlight

(28:08) Designing your day with a calendar

(30:52) The Groundhog Day mentality

(35:10) Tactical advice for implementing the highlight method

(39:30) An example of a failed highlight

(48:08) Step 2: Laser

(51:12) Creating intentional friction to avoid distractions

(57:28) Curating a distraction-free phone

(01:07:58) Resetting expectations and slowing your inbox

(01:14:51) Systems over willpower

(01:18:14) Managing email distractions

(01:18:49) Step 3: Energize

(01:22:05) Step 4: Reflect

(01:26:30) Introduction to Sprint

Referenced:

Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY

• Make Time blog: https://maketime.blog/

• Make Time blog on X: https://twitter.com/maketimeblog

• Character: https://www.character.vc/

• Google Ventures: https://www.gv.com/

• Character Labs: https://www.character.vc/labs

• Strategies for becoming less distracted and improving focus | Nir Eyal (author of Indistractable and Hooked): https://www.lennyspodcast.com/strategies-for-becoming-less-distracted-and-improving-focus-nir-eyal-author-of-indistractable-and/

Groundhog Day on Prime Video: https://www.amazon.com/Groundhog-Day-Bill-Murray/dp/B000SP1SH6

• Reclaim.ai: https://reclaim.ai/

• Feed Blocker for LinkedIn: https://chromewebstore.google.com/detail/feed-blocker-for-linkedin/eikaafmldiioljlilngpogcepiedpenf

The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411

• MagSafe charger: https://www.amazon.com/Apple-MHXH3AM-A-MagSafe-Charger/dp/B08L5NP6NG/

• Nanit app: https://www.nanit.com/pages/nanit-app

• Arianna Huffington’s Phone Bed Charging Station: https://www.amazon.com/Arianna-Huffingtons-Charging-Station-Walnut/dp/B0799ZG1LY

• Cell Phone Lock Box with Timer: https://www.amazon.com/Portable-Android-Self-Discipline-Achieve-Addiction/dp/B0CG8V4YG3?th=1

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357

The Economist: https://www.economist.com/

• Odysseus: https://www.britannica.com/topic/Odysseus

• Mailman: https://www.mailmanhq.com/

• Future: https://www.future.co/

• Notion: https://www.notion.so/

• Miro: https://miro.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Jake Knapp and John Zeratsky are the authors of best-selling books Sprint and Make Time. They have helped more than 300 teams design new products and bring them to market, including those at YouTube, Gusto, One Medical Group, and Slack. Jake and John are co-founders of the venture capital firm Character, where they support startups with capital and sprints. Previously, they were operating partners at Google Ventures and, before that, design leaders at Google, where John worked on Google Ads and YouTube and Jake helped build Gmail and co-founded Google Meet. In our conversation, we discuss:

• “Busy bandwagon” and “infinity pools”

• Creating one “highlight” each day

• Their four-part framework for productivity

• How to use the calendar to design your day

• How creating friction can help you avoid distractions

• Tips on creating a distraction-free phone

• Strategies for managing email and distractions

• The importance of reflecting on the day and making time for meaningful work

• Design sprints

Brought to you by:

Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

Whimsical—The iterative product workspace

WorkOS—The modern API for auth and user identity

Find the full transcript at: https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake

Where to find Jake Knapp:

• X: https://twitter.com/jakek

• LinkedIn: https://www.linkedin.com/in/jake-knapp/

• Website: https://jakeknapp.com/

Where to find John Zeratsky:

• X: https://twitter.com/jazer

• LinkedIn: https://www.linkedin.com/in/johnzeratsky/

• Website: https://johnzeratsky.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) About Jake and John

(04:10) Recording the audiobook for Make Time

(06:06) What people often get wrong when trying to become more productive

(11:24) The busy bandwagon and infinity pools

(15:22) Real talk: Jake and John’s productivity levels

(20:10) The four-part framework for getting more done: Highlight, Laser, Energize, Reflect

(25:15) Step 1: Highlight

(28:08) Designing your day with a calendar

(30:52) The Groundhog Day mentality

(35:10) Tactical advice for implementing the highlight method

(39:30) An example of a failed highlight

(48:08) Step 2: Laser

(51:12) Creating intentional friction to avoid distractions

(57:28) Curating a distraction-free phone

(01:07:58) Resetting expectations and slowing your inbox

(01:14:51) Systems over willpower

(01:18:14) Managing email distractions

(01:18:49) Step 3: Energize

(01:22:05) Step 4: Reflect

(01:26:30) Introduction to Sprint

Referenced:

Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY

• Make Time blog: https://maketime.blog/

• Make Time blog on X: https://twitter.com/maketimeblog

• Character: https://www.character.vc/

• Google Ventures: https://www.gv.com/

• Character Labs: https://www.character.vc/labs

• Strategies for becoming less distracted and improving focus | Nir Eyal (author of Indistractable and Hooked): https://www.lennyspodcast.com/strategies-for-becoming-less-distracted-and-improving-focus-nir-eyal-author-of-indistractable-and/

Groundhog Day on Prime Video: https://www.amazon.com/Groundhog-Day-Bill-Murray/dp/B000SP1SH6

• Reclaim.ai: https://reclaim.ai/

• Feed Blocker for LinkedIn: https://chromewebstore.google.com/detail/feed-blocker-for-linkedin/eikaafmldiioljlilngpogcepiedpenf

The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411

• MagSafe charger: https://www.amazon.com/Apple-MHXH3AM-A-MagSafe-Charger/dp/B08L5NP6NG/

• Nanit app: https://www.nanit.com/pages/nanit-app

• Arianna Huffington’s Phone Bed Charging Station: https://www.amazon.com/Arianna-Huffingtons-Charging-Station-Walnut/dp/B0799ZG1LY

• Cell Phone Lock Box with Timer: https://www.amazon.com/Portable-Android-Self-Discipline-Achieve-Addiction/dp/B0CG8V4YG3?th=1

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357

The Economist: https://www.economist.com/

• Odysseus: https://www.britannica.com/topic/Odysseus

• Mailman: https://www.mailmanhq.com/

• Future: https://www.future.co/

• Notion: https://www.notion.so/

• Miro: https://miro.com/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Logan Kilpatrick leads developer relations at OpenAI, supporting developers building with the OpenAI API and ChatGPT. He is also on the board of directors at NumFOCUS, the nonprofit organization that supports open source projects like Jupyter, Pandas, NumPy, and more. Before OpenAI, Logan was a machine-learning engineer at Apple and advised NASA on open source policy. In our conversation, we discuss:

• OpenAI’s fast-paced and innovative work environment

• The value of high agency and high urgency in your employees

• Tips for writing better ChatGPT prompts

• How the GPT Store is doing

• OpenAI’s planning process and decision-making criteria

• Where OpenAI is heading in the next few years

• Insight into OpenAI’s B2B offerings

• Why Logan “measures in hundreds”

Brought to you by:

Hex—Helping teams ask and answer data questions by working together

Whimsical—The iterative product workspace

Arcade Software—Create effortlessly beautiful demos in minutes

Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/inside-openai-logan-kilpatrick-head

Today’s transcript will be live by 8 a.m. PT.

Where to find Logan Kilpatrick:

• X: https://twitter.com/OfficialLoganK

• LinkedIn: https://www.linkedin.com/in/logankilpatrick/

• Website: https://logank.ai/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Logan’s background

(03:49) The impact of recent events on OpenAI’s team and culture

(08:20) Exciting developments in AI interfaces

(09:52) Using OpenAI tools to make companies more efficient

(13:04) Examples of using AI effectively

(18:35) Prompt engineering

(22:12) How to write better prompts

(26:05) The launch of GPTs and the OpenAI Store

(32:10) The importance of high agency and urgency

(34:35) OpenAI’s ability to move fast and ship high-quality products

(35:56) OpenAI’s planning process and decision-making criteria

(40:22) The importance of real-time communication

(42:33) OpenAI’s team and growth

(44:47) Future developments at OpenAI

(47:42) GPT-5 and building toward the future

(50:38) OpenAI’s enterprise offering and the value of sharing custom applications

(52:30) New updates and features from OpenAI

(55:09) How to leverage OpenAI’s technology in products

(58:26) Encouragement for building with AI

(59:30) Lightning round

Referenced:

• OpenAI: https://openai.com/

• Sam Altman on X: https://twitter.com/sama

• Greg Brockman on X: https://twitter.com/gdb

• tldraw: https://www.tldraw.com/

• Harvey: https://www.harvey.ai/

• Boost Your Productivity with Generative AI: https://hbr.org/2023/06/boost-your-productivity-with-generative-ai

• Research: quantifying GitHub Copilot’s impact on developer productivity and happiness: https://github.blog/2022-09-07-research-quantifying-github-copilots-impact-on-developer-productivity-and-happiness/

• Lesson learnt from the DPD AI Chatbot swearing blunder: https://www.linkedin.com/pulse/lesson-learnt-from-dpd-ai-chatbot-swearing-blunder-kitty-sz57e/

• Dennis Yang on LinkedIn: https://www.linkedin.com/in/dennisyang/

• Tim Ferriss’s blog: https://tim.blog/

• Tyler Cowen on X: https://twitter.com/tylercowen

• Tom Cruise on X: https://twitter.com/TomCruise

• Canva: https://www.canva.com/

• Zapier: https://zapier.com/

• Siqi Chen on X: https://twitter.com/blader

• Runway: https://runway.com/

• Universal Primer: https://chat.openai.com/g/g-GbLbctpPz-universal-primer

• “I didn’t expect ChatGPT to get so good” | Unconfuse Me with Bill Gates: https://www.youtube.com/watch?v=8-Ymdc6EdKw

• Microsoft Azure: https://azure.microsoft.com/

• Lennybot: https://www.lennybot.com/

• Visual Electric: https://visualelectric.com/

• DALL-E: https://openai.com/research/dall-e

The One World Schoolhouse: https://www.amazon.com/One-World-Schoolhouse-Education-Reimagined/dp/1455508373/ref=sr_1_1

Why We Sleep: Unlocking the Power of Sleep and Dreams: https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144324

Gran Turismo: https://www.netflix.com/title/81672085

Gran Turismo video game: https://www.playstation.com/en-us/gran-turismo/

• Manta sleep mask: https://mantasleep.com/products/manta-sleep-mask

• WAOAW sleep mask: https://www.amazon.com/WAOAW-Sleep-Sleeping-Blocking-Blindfold/dp/B09712FSLY

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Logan Kilpatrick leads developer relations at OpenAI, supporting developers building with the OpenAI API and ChatGPT. He is also on the board of directors at NumFOCUS, the nonprofit organization that supports open source projects like Jupyter, Pandas, NumPy, and more. Before OpenAI, Logan was a machine-learning engineer at Apple and advised NASA on open source policy. In our conversation, we discuss:

• OpenAI’s fast-paced and innovative work environment

• The value of high agency and high urgency in your employees

• Tips for writing better ChatGPT prompts

• How the GPT Store is doing

• OpenAI’s planning process and decision-making criteria

• Where OpenAI is heading in the next few years

• Insight into OpenAI’s B2B offerings

• Why Logan “measures in hundreds”

Brought to you by:

Hex—Helping teams ask and answer data questions by working together

Whimsical—The iterative product workspace

Arcade Software—Create effortlessly beautiful demos in minutes

Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/inside-openai-logan-kilpatrick-head

Today’s transcript will be live by 8 a.m. PT.

Where to find Logan Kilpatrick:

• X: https://twitter.com/OfficialLoganK

• LinkedIn: https://www.linkedin.com/in/logankilpatrick/

• Website: https://logank.ai/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Logan’s background

(03:49) The impact of recent events on OpenAI’s team and culture

(08:20) Exciting developments in AI interfaces

(09:52) Using OpenAI tools to make companies more efficient

(13:04) Examples of using AI effectively

(18:35) Prompt engineering

(22:12) How to write better prompts

(26:05) The launch of GPTs and the OpenAI Store

(32:10) The importance of high agency and urgency

(34:35) OpenAI’s ability to move fast and ship high-quality products

(35:56) OpenAI’s planning process and decision-making criteria

(40:22) The importance of real-time communication

(42:33) OpenAI’s team and growth

(44:47) Future developments at OpenAI

(47:42) GPT-5 and building toward the future

(50:38) OpenAI’s enterprise offering and the value of sharing custom applications

(52:30) New updates and features from OpenAI

(55:09) How to leverage OpenAI’s technology in products

(58:26) Encouragement for building with AI

(59:30) Lightning round

Referenced:

• OpenAI: https://openai.com/

• Sam Altman on X: https://twitter.com/sama

• Greg Brockman on X: https://twitter.com/gdb

• tldraw: https://www.tldraw.com/

• Harvey: https://www.harvey.ai/

• Boost Your Productivity with Generative AI: https://hbr.org/2023/06/boost-your-productivity-with-generative-ai

• Research: quantifying GitHub Copilot’s impact on developer productivity and happiness: https://github.blog/2022-09-07-research-quantifying-github-copilots-impact-on-developer-productivity-and-happiness/

• Lesson learnt from the DPD AI Chatbot swearing blunder: https://www.linkedin.com/pulse/lesson-learnt-from-dpd-ai-chatbot-swearing-blunder-kitty-sz57e/

• Dennis Yang on LinkedIn: https://www.linkedin.com/in/dennisyang/

• Tim Ferriss’s blog: https://tim.blog/

• Tyler Cowen on X: https://twitter.com/tylercowen

• Tom Cruise on X: https://twitter.com/TomCruise

• Canva: https://www.canva.com/

• Zapier: https://zapier.com/

• Siqi Chen on X: https://twitter.com/blader

• Runway: https://runway.com/

• Universal Primer: https://chat.openai.com/g/g-GbLbctpPz-universal-primer

• “I didn’t expect ChatGPT to get so good” | Unconfuse Me with Bill Gates: https://www.youtube.com/watch?v=8-Ymdc6EdKw

• Microsoft Azure: https://azure.microsoft.com/

• Lennybot: https://www.lennybot.com/

• Visual Electric: https://visualelectric.com/

• DALL-E: https://openai.com/research/dall-e

The One World Schoolhouse: https://www.amazon.com/One-World-Schoolhouse-Education-Reimagined/dp/1455508373/ref=sr_1_1

Why We Sleep: Unlocking the Power of Sleep and Dreams: https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144324

Gran Turismo: https://www.netflix.com/title/81672085

Gran Turismo video game: https://www.playstation.com/en-us/gran-turismo/

• Manta sleep mask: https://mantasleep.com/products/manta-sleep-mask

• WAOAW sleep mask: https://www.amazon.com/WAOAW-Sleep-Sleeping-Blocking-Blindfold/dp/B09712FSLY

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Megan Cook is the head of product for Atlassian’s Jira software, which is used by 75% of Fortune 500 companies, has over 125,000 customers globally, over 15 different products, and is by far the most popular project management tool in the world. Megan has been at Atlassian for just under 11 years, and before this role, she was an analyst, a developer, and an Agile coach. In our conversation, we discuss:

• How to get buy-in for your ideas

• The value of starting small

• How, and why, creating space for play is so essential

• How Jira stays ahead of endless competition

• Atlassian’s approach to launching new product lines

• Tactical tips for making remote work, work

• A personal failure and the lessons learned from it

Brought to you by:

Teal—Your personal career growth platform

Sprig—Build a product people love

Vanta—Automate compliance. Simplify security.

Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

Today’s transcript will be live by 8 a.m. PT.

Where to find Megan Cook:

• X: https://twitter.com/meganwcook

• LinkedIn: https://www.linkedin.com/in/cookmegan

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Megan’s background

(03:50) Creating space for play and psychological safety on teams

(07:36) Peer feedback groups

(10:30) Sharing stories of failure

(13:33) The “10 dollar” game for priorities

(15:24) Advice on making remote work, work

(24:16) Getting buy-in for your ideas

(28:33) The importance of staying open-minded

(34:05) A quick summary of how to get buy-in

(36:45) Fighting the good fight

(38:15) Identifying customer pain points

(43:04) Starting small and showing success

(46:08) Launching new product lines

(53:35) Atlassian’s gated process for new product ideas

(58:00) How Jira stays ahead of competitors

(01:04:28) Learning from failure

(01:08:30) Fight club

(01:10:08) Lightning round

Referenced:

• Jira: https://www.atlassian.com/software/jira

• Atlassian: https://www.atlassian.com/

• Bitbucket: https://bitbucket.org/product

• Ben Crowe on LinkedIn: https://www.linkedin.com/in/ben-crowe-67299714/

• Ash Barty on X: https://twitter.com/ashbarty

• Atlassian’s blog, Work Life: https://www.atlassian.com/blog

• Lessons learned: 1,000 days of distributed at Atlassian: https://www.atlassian.com/blog/distributed-work/distributed-work-report

• New research: How to make time for the work that matters: https://www.atlassian.com/blog/distributed-work/calendar-redesign-experiment

• Atlas: https://www.atlassian.com/software/atlas

• Confluence: https://www.atlassian.com/software/confluence

• Lenny’s swag store: https://lennyswag.com/

• What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat

• The UX research reckoning is here | Judd Antin (Airbnb, Meta): https://www.lennyspodcast.com/the-ux-research-reckoning-is-here-judd-antin-airbnb-meta/

• Charlie Sutton on LinkedIn: https://www.linkedin.com/in/charliesutton/

• Nokia 6100: https://en.wikipedia.org/wiki/Nokia_6100

• Compass: https://www.atlassian.com/software/compass

• Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

• Canva: https://www.canva.com/

Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3

Foundation book series: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573

• Traeger smoker: https://www.traeger.com/shop/wood-pellet-grills

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
More description

Megan Cook is the head of product for Atlassian’s Jira software, which is used by 75% of Fortune 500 companies, has over 125,000 customers globally, over 15 different products, and is by far the most popular project management tool in the world. Megan has been at Atlassian for just under 11 years, and before this role, she was an analyst, a developer, and an Agile coach. In our conversation, we discuss:

• How to get buy-in for your ideas

• The value of starting small

• How, and why, creating space for play is so essential

• How Jira stays ahead of endless competition

• Atlassian’s approach to launching new product lines

• Tactical tips for making remote work, work

• A personal failure and the lessons learned from it

Brought to you by:

Teal—Your personal career growth platform

Sprig—Build a product people love

Vanta—Automate compliance. Simplify security.

Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

Today’s transcript will be live by 8 a.m. PT.

Where to find Megan Cook:

• X: https://twitter.com/meganwcook

• LinkedIn: https://www.linkedin.com/in/cookmegan

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Megan’s background

(03:50) Creating space for play and psychological safety on teams

(07:36) Peer feedback groups

(10:30) Sharing stories of failure

(13:33) The “10 dollar” game for priorities

(15:24) Advice on making remote work, work

(24:16) Getting buy-in for your ideas

(28:33) The importance of staying open-minded

(34:05) A quick summary of how to get buy-in

(36:45) Fighting the good fight

(38:15) Identifying customer pain points

(43:04) Starting small and showing success

(46:08) Launching new product lines

(53:35) Atlassian’s gated process for new product ideas

(58:00) How Jira stays ahead of competitors

(01:04:28) Learning from failure

(01:08:30) Fight club

(01:10:08) Lightning round

Referenced:

• Jira: https://www.atlassian.com/software/jira

• Atlassian: https://www.atlassian.com/

• Bitbucket: https://bitbucket.org/product

• Ben Crowe on LinkedIn: https://www.linkedin.com/in/ben-crowe-67299714/

• Ash Barty on X: https://twitter.com/ashbarty

• Atlassian’s blog, Work Life: https://www.atlassian.com/blog

• Lessons learned: 1,000 days of distributed at Atlassian: https://www.atlassian.com/blog/distributed-work/distributed-work-report

• New research: How to make time for the work that matters: https://www.atlassian.com/blog/distributed-work/calendar-redesign-experiment

• Atlas: https://www.atlassian.com/software/atlas

• Confluence: https://www.atlassian.com/software/confluence

• Lenny’s swag store: https://lennyswag.com/

• What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat

• The UX research reckoning is here | Judd Antin (Airbnb, Meta): https://www.lennyspodcast.com/the-ux-research-reckoning-is-here-judd-antin-airbnb-meta/

• Charlie Sutton on LinkedIn: https://www.linkedin.com/in/charliesutton/

• Nokia 6100: https://en.wikipedia.org/wiki/Nokia_6100

• Compass: https://www.atlassian.com/software/compass

• Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

• Canva: https://www.canva.com/

Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3

Foundation book series: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573

• Traeger smoker: https://www.traeger.com/shop/wood-pellet-grills

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
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