Lenny's Podcast: Product | Career | Growth

Jonny Miller is the founder of Nervous System Mastery, a course that has helped hundreds of founders and tech leaders cultivate calm, reduce nervousness, enhance resilience, and elevate their sense of aliveness. Having personally benefited from Jonny’s teachings, I’m especially excited to have him on the show. In this episode, we discuss:

• How shifting your focus from the mind to the body can help ease nervousness

• The power of breath in changing states

• The importance of “interoception”

• Specific breathing exercises to both calm and excite your nervous system

• The A.P.E. (awareness, posture, and emotion) framework for recognizing body signals

• The “feather, brick, dump truck” phenomenon

• The concept of emotional debt and how to release it

• The competitive advantage of feeling emotions

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Jonny’s five-week boot camp, Nervous System Mastery, will equip you with evidence-backed protocols to cultivate greater calm and agency over your internal state. Learn to rewire maladaptive stress responses and improve your sleep (use code LENNY for $250 discount). Apply here.

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Brought to you by:

• Teal—Your personal career growth platform

• Vanta—Automate compliance. Simplify security.

• Miro—A collaborative visual platform where your best work comes to life

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Find the full transcript at: https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

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Where to find Jonny Miller:

• X: https://twitter.com/jonnym1ller

• LinkedIn: https://www.linkedin.com/in/jonnym1ller/

• Website: https://www.jonnymiller.co/

• Podcast: podcast.curioushumans.com 

• Email: jonny@curioushumans.com

• Course: https://nsmastery.com/lenny

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Jonny’s background

(07:19) The bottom-up approach to nervousness and anxiety

(09:42) The power of breath in changing states

(11:47) The concept of state over story

(13:56) Personal experiences with nervousness

(15:01) Breathing exercises to calm you down

(20:40) The “espresso” breath exercise to give you energy

(25:44) Interoception and the A.P.E. framework

(34:47) The “feather, brick, dump truck” phenomenon

(37:40) Recognizing emotional debt and avoiding burnout

(40:47) Using somatic-oriented therapy for healing

(45:26) Telltale signs of emotional debt

(48:13) The competitive advantage of “feeling the feels”

(50:20) Advice for people overwhelmed by stimuli

(52:36) The NSDR (non-sleep deep rest) practice for emotional release

(55:38) Daily practices for emotional well-being

(58:23) Thoughts on meditation

(01:01:26) The Body Keeps the Score

(01:01:58) Contrarian corner

(01:04:43) Lightning round

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Jonny’s If [This] Then [Breathe] Recipes:

• If [overwhelmed], then [hum]

• If [anxious], then [breath of calm]

• If [lethargic], then [espresso breath]

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Referenced:

• The Operating Manual for Your Nervous System: https://every.to/p/the-operating-manual-for-your-nervous-system

• Afferent vs. Efferent Neurons: https://www.osmosis.org/answers/afferent-vs-efferent-neurons

• Insular cortex: https://en.wikipedia.org/wiki/Insular_cortex

• Jonny’s TED Talk, “The gifts of grief”: https://www.ted.com/talks/jonny_miller_the_gifts_of_grief/details

• Humming (Simple Bhramari Pranayama) as a Stress Buster: A Holter-Based Study to Analyze Heart Rate Variability (HRV) Parameters During Bhramari, Physical Activity, Emotional Stress, and Sleep: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10182780/

• 14-Minute Guided NSDR (non-sleep deep rest) practice: https://www.youtube.com/watch?v=vjXX2c72fYY

• Breathing Techniques to Reduce Stress and Anxiety | Dr. Andrew Huberman on the Physiological Sigh: https://www.youtube.com/watch?v=kSZKIupBUuc

• Interoception: the hidden sense that shapes well-being: https://www.theguardian.com/science/2021/aug/15/the-hidden-sense-shaping-your-wellbeing-interoception

• Exteroception: https://dictionary.apa.org/exteroception

• Interoceptive Awareness and ADHD: https://chadd.org/adhd-news/adhd-news-adults/interoceptive-awareness-and-adhd/

• Childhood Trauma Affects Stress-Related Interoceptive Accuracy: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6813623/

• The Hour Between Dog and Wolf: How Risk Taking Transforms Us, Body and Mind: https://www.amazon.com/Hour-Between-Dog-Wolf-Transforms/dp/0143123408

• Somatic Experiencing: https://www.somaticexperiencing.com/

• Hakomi Institute: https://hakomiinstitute.com/

• Decisions and Desire (about Antonio Damasio’s work): https://hbr.org/2006/01/decisions-and-desire

• When enough is enough | Andy Johns (ex-FB, Twitter, Quora): https://www.lennyspodcast.com/when-enough-is-enough-andy-johns-ex-fb-twitter-quora/

• What Is Yoga Nidra?: https://health.clevelandclinic.org/what-is-yoga-nidra

• Becoming Fully Yourself, What AI Wants, Family Rituals & Rites of Passage, with Kevin Kelly: https://podcast.curioushumans.com/episodes/becoming-fully-yourself-what-ai-wants-rites-of-passage-with-kevin-kelly

• Tim Ferriss: https://tim.blog/

• The Power of Sensations: Intermediate’s Vipassana Body Scan: https://insighttimer.com/carola.ananda/guided-meditations/the-power-of-sensations-intermediates-vipassana-body-scan-meditation

• Vipassana Meditation: https://www.dhamma.org/en/index

• The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma: https://www.amazon.com/Body-Keeps-Score-Healing-Trauma/dp/0670785938

• Waking the Tiger: Healing Trauma: https://www.amazon.com/Waking-Tiger-Healing-Peter-Levine/dp/155643233X

• Consolations: The Solace, Nourishment and Underlying Meaning of Everyday Words: https://www.themarginalian.org/2015/04/29/david-whyte-consolations-words/

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904/

• The Conscious Leadership Group: https://conscious.is/

• Recapture the Rapture: Rethinking God, Sex, and Death in a World That’s Lost Its Mind: https://www.amazon.com/Recapture-Rapture-Rethinking-Death-World/dp/0062905465

• Kubo and the Two Strings on Prime Video: https://www.amazon.com/Kubo-Two-Strings-Charlize-Theron/dp/B01K5BSWX0

• Wolfwalkers on AppleTV+: https://tv.apple.com/us/movie/wolfwalkers/umc.cmc.amuoq00hqelfi98j0gvg641x

• Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

• Jerry Colonna on LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/

• Ra Optics “Sunset” blue-light blockers: https://raoptics.com/collections/night-lenses

• Nurosym vagal stimulation device: https://my.nurosym.com/vns1564/

• Pulsetto vagal stimulation device: https://pulsetto.tech/new-year/?gc_id=20124962116&h_ad_id=686249897188&gad_source=1

• Apollo vagus nerve stimulator: https://apolloneuro.com/products/apollo-wearable

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Additional research:

• Cellular allostatic load is linked to increased energy expenditure and accelerated biological aging: https://www.sciencedirect.com/science/article/pii/S0306453023003001

• Somatic experiencing: using interoception and proprioception as core elements of trauma therapy: https://www.frontiersin.org/articles/10.3389/fpsyg.2015.00093/full

• Relationship between interoception and emotion regulation: New evidence from mixed methods: https://www.sciencedirect.com/science/article/abs/pii/S0165032718323723

• Out-of-the-blue panic attacks aren’t without warning: body sends signals for hour before: https://pubmed.ncbi.nlm.nih.gov/21783179/

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

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Lenny may be an investor in the companies discussed.

Geoffrey Moore is an author, speaker, and advisor, widely known for his seminal book Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers, which many consider the most important book ever written on go-to-market strategy. Moore’s work is focused on the market dynamics surrounding disruptive innovations, and how one overcomes the challenge of transitioning from serving early adopters to the mainstream. In this episode, we discuss:

• What “crossing the chasm” means

• What steps to take before you try crossing the chasm

• The importance of winning a marquee customer

• The role of executive sponsors in the sales process

• The differences between visionaries and pragmatists, and how to build for each

• Geoffrey’s four go-to-market playbooks based on stage: Early Market, Bowling Alley, Tornado, and Main Street

• The problem with discounting before crossing the chasm

• “Deadly sins” to avoid when crossing the chasm

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Brought to you by:

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

• WorkOS—An API platform for quickly adding enterprise features

• Arcade Software—Create effortlessly beautiful demos in minutes

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Find the full transcript at: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

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Where to find Geoffrey Moore:

• X: https://twitter.com/geoffreyamoore

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

• LinkedIn posts: https://www.linkedin.com/in/geoffreyamoore/recent-activity/articles/

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Geoffrey’s background

(04:03) What people often get wrong about Crossing the Chasm

(05:58) Finding your beachhead segment

(09:29) The four inflection points of the technology adoption lifestyle

(15:45) Geoffrey’s bonfire and bowling alley analogies

(18:36) Steps to take before trying to cross the chasm

(22:19) Signs you’re ready to cross the chasm

(25:19) Advice for startups on where to start

(27:31) Thoughts on venture capital

(27:53) A general timeline for crossing the chasm

(30:52) What exactly is the “chasm”?

(32:35) The difference between visionaries and pragmatists

(36:05) Finding the compelling reason to buy

(43:45) The Early Market playbook

(45:46) The Bowling Alley playbook

(48:39) Different sales approaches for early market and bowling alley

(51:26) Changing the value state of the company

(53:28) The Tornado playbook

(57:35) Why combining playbooks doesn’t work

(59:10) Using generative AI in different market phases

(01:03:02) The risks of discounting

(01:04:21) Other “deadly sins” of crossing the chasm

(01:09:09) Positioning in crossing the chasm

(01:10:36) Product-led growth and crossing the chasm

(01:13:54) The challenges of software and entrepreneurship

(01:16:35) How Geoffrey’s thinking has evolved

(01:19:30) The importance of entrepreneurship and impact

(01:20:42) His book The Infinite Staircase

(01:23:58) Connect with Geoffrey Moore

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Referenced:

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• Oracle: https://www.oracle.com/

• Documentum: https://www.opentext.com/products/documentum

• Figma: https://www.figma.com/

• Notion: https://www.notion.so/

• Salesforce: https://www.salesforce.com/

• Intel: https://www.intel.com/

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennyspodcast.com/jason-fried-challenges-your-thinking-on-fundraising-goals-growth-and-more/

• The Mayo Clinic: https://www.mayoclinic.org/

• Coda: https://coda.io/

• An inside look at how Figma ships product: https://coda.io/@yuhki/figma-product-roadmap

• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

• Regis McKenna on Crunchbase: https://www.crunchbase.com/organization/regis-mckenna-inc

• Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove

• 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/

• Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand/dp/1999023021

• B2B Go-to-Market Playbooks and the Technology Adoption Life Cycle: https://www.linkedin.com/pulse/b2b-go-to-market-playbooks-technology-adoption-life-cycle-moore/

• Juniper: https://www.juniper.net/us/en.html

• Sal Khan on LinkedIn: https://www.linkedin.com/in/khanacademy/

• Khan Academy: https://www.khanacademy.org/

• How the Star Wars Kessel Run Turns Han Solo Into a Time-Traveler: https://www.wired.com/2013/02/kessel-run-12-parsecs/

• Atlassian: https://www.atlassian.com/

• Martin Casado on LinkedIn: https://www.linkedin.com/in/martincasado/

• The Infinite Staircase: What the Universe Tells Us About Life, Ethics, and Mortality: https://www.amazon.com/Infinite-Staircase-Universe-Ethics-Mortality/dp/1950665984

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

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Lenny may be an investor in the companies discussed.

Richard Rumelt is a legend in the world of strategy. He’s the author of Good Strategy/Bad Strategy and The Crux: How Leaders Become Strategists, both of which are often recommended by guests on this podcast. From his early days teaching in Iran at a Harvard-sponsored business school to teaching at Harvard Business School itself to over four decades teaching at UCLA’s Anderson School of Management, Richard’s impact resonates globally. His strategic insights are sought after by major corporations including Microsoft, Shell, Apple, AT&T, Intel, and Commonwealth Bank and by governmental organizations such as the U.S. Army Special Operations Command. In this episode, we discuss:

• The essential components of a good strategy

• The importance of coherence in strategy

• Common pitfalls that create a bad strategy

• How “power” plays into strategy, and common sources of power

• The value of knowing history when developing effective strategies

• Why a strategy should simply be called an “action agenda”

• The need for one decider in an organization

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Brought to you by:

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

• Miro—A collaborative visual platform where your best work comes to life

• Vanta—Automate compliance. Simplify security.

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Find the full transcript at: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

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Where to find Richard Rumelt:

• Email: richard@generalimagination.com

• LinkedIn: https://www.linkedin.com/in/richard-rumelt-18520828/

• Website: https://thecruxbook.com/

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Richard’s background

(04:29) What is a strategy?

(06:23) The essential components of a good strategy (the “kernel”)

(15:04) An example of good strategy

(16:55) Bad strategy

(25:17) The importance of focus and power

(28:19) Identifying and utilizing power

(34:38) Types of power

(41:13) Implementing power

(48:15) The importance of historical knowledge

(55:23) How to write an action agenda

(01:02:47) The crux

(01:10:40) Challenges to executing a strategy

(01:15:44) The need for a decider

(01:20:39) Strategy for startups

(01:26:04) Richard’s “value denials” exercise

(01:31:01) Closing thoughts

(01:33:57) Lightning round

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Referenced:

• China’s Xi says ‘reunification’ with Taiwan is inevitable: https://www.cnbc.com/2023/12/31/chinas-xi-says-reunification-with-taiwan-is-inevitable.html

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240

• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

• Fundamental Issues in Strategy: A Research Agenda: https://www.amazon.com/Fundamental-Issues-Strategy-Research-Agenda/dp/0875843433/

• Strategy, Structure, and Economic Performance: https://www.amazon.com/Strategy-Structure-Economic-Performance-Richard/dp/0875841090

• There’s more than the CIA and FBI: The 17 agencies that make up the U.S. intelligence community: https://www.latimes.com/nation/la-na-17-intelligence-agencies-20170112-story.html

• Programme for International Student Assessment: https://www.oecd.org/pisa/

• Gerstner: Changing Culture at IBM—Lou Gerstner Discusses Changing the Culture at IBM: https://hbswk.hbs.edu/archive/gerstner-changing-culture-at-ibm-lou-gerstner-discusses-changing-the-culture-at-ibm

• Marvin Lieberman on LinkedIn: https://www.linkedin.com/in/marvin-lieberman-2a6b72/

• S&P 500: https://www.spglobal.com/spdji/en/indices/equity/sp-500/#overview

• Battle of Tora Bora: https://en.wikipedia.org/wiki/Battle_of_Tora_Bora

• Milton Friedman: https://en.wikipedia.org/wiki/Milton_Friedman

• The Louvre: https://www.louvre.fr/en

• How does SpaceX build its Falcon 9 reusable rocket?: https://www.sciencefocus.com/space/how-does-spacex-build-its-falcon-9-reusable-rocket

• Charles Darwin: History’s most famous biologist: https://www.nhm.ac.uk/discover/charles-darwin-most-famous-biologist.html

• Donald Rumsfeld: https://www.defense.gov/About/Biographies/Biography/Article/602800/

• Bush: The Decider-in-Chief: https://www.cbsnews.com/news/bush-the-decider-in-chief/

• Woodrow Wilson: https://www.whitehouse.gov/about-the-white-house/presidents/woodrow-wilson/

• How the Sinking of Lusitania Changed World War I: https://www.history.com/news/how-the-sinking-of-lusitania-changed-wwi

• Nokia: https://www.nokia.com/

• The Rise and Fall of Nokia: https://www.hbs.edu/faculty/Pages/item.aspx?num=46041

• Salesforce: https://www.salesforce.com/

• These New Windows Let the Summer Breeze In, But Block the Street Noise: https://www.smithsonianmag.com/smart-news/these-new-windows-let-the-summer-breeze-in-but-block-the-street-noise-7906121/

• Stop it! (Bob Newhart): https://www.youtube.com/watch?v=jvujypVVBAY

• The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244

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

• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1982176865

• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821

• Titan: The Life of John D. Rockefeller, Sr.: https://www.amazon.com/Titan-Life-John-Rockefeller-Sr/dp/1400077303/

• Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone

• Smart telescopes: https://milehighastro.com/collections/smart-telescopes

• Cassandra Clare: https://cassandraclare.com/

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

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Lenny may be an investor in the companies discussed.

Heidi Helfand is the author of Dynamic Reteaming, which outlines practical strategies for orchestrating successful team and company org changes. Her work is informed by more than 20 years in the tech industry at notable companies like AppFolio, Procore, and Expertcity/GoToMeeting. Today, she dedicates her efforts to sharing her knowledge through workshops, comprehensive courses, and consultative services, helping organizations navigate and optimize their team structures. In this episode, we discuss:

• The importance of reteaming and reorging

• The benefits of embracing reteaming

• The five patterns of reteaming: one by one, grow and split, merging, isolation, and switching

• Examples of successful reteaming

• Why stable teams are not always ideal

• How change can lead to great career opportunities

• The RIDE framework for decision-making

• Advice on how to set up isolated teams for success

• The anti-patterns of reteaming and the challenges that can arise

• Tactical tips for becoming a better listener

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Brought to you by:

• Productroadmap.ai—AI to connect your roadmaps to revenue

• Hex—Helping teams ask and answer data questions by working together

• Ahrefs—Improve your website’s SEO for free

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Find the full transcript at: https://www.lennysnewsletter.com/p/the-art-and-wisdom-of-changing-teams

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Where to find Heidi Helfand:

• X: https://twitter.com/heidihelfand

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

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

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Heidi’s background

(03:40) How Heidi got involved with reteaming and reorgs

(07:37) Advice for people dealing with reorgs

(11:56) The benefits of change and the RIDE framework

(17:11) The five patterns of reteaming

(20:00) The power of isolation

(27:38) Advice on how to be successful by isolating small teams

(33:27) Supporting and protecting internal startups

(34:33) The one-by-one pattern

(36:44) The grow and split pattern

(39:20) The merging pattern

(42:14) The switching pattern

(50:18) Anti-patterns of reteaming

(52:49) Embracing change and growth

(58:48) How to become a better listener

(01:01:28) Lightning round

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Referenced:

• Dynamic Reteaming: The Art and Wisdom of Changing Teams: https://www.amazon.com/Dynamic-Reteaming-Wisdom-Changing-Teams/dp/1492061298

• O’Reilly: https://www.oreilly.com/

• Procore Technologies: https://www.procore.com/

• Kristian Lindwall on LinkedIn: https://www.linkedin.com/in/kristianlindwall/

• Chris Smith on LinkedIn: https://www.linkedin.com/in/chrissmithagile

• Transitions: Making Sense of Life’s Changes: https://www.amazon.com/Transitions-Making-Changes-Revised-Anniversary/dp/073820904X

• Pat Wadors on LinkedIn: https://www.linkedin.com/in/patwadors/

• The Four Steps to the Epiphany: Successful Strategies for Products That Win: https://www.amazon.com/Four-Steps-Epiphany-Successful-Strategies/dp/1119690358

• GoToMyPC: https://get.gotomypc.com/

• Teamwork: https://www.amazon.com/Teamwork-Right-Wrong-Interpersonal-Communication/dp/0803932901

• AppFolio: https://www.appfolio.com/

• SecureDocs: https://www.securedocs.com/

• Citrix: https://www.citrix.com/

• The Culture Code: The Secrets of Highly Successful Groups: https://www.amazon.com/Culture-Code-Secrets-Highly-Successful/dp/0804176981

• Tuckman’s stages of group development: https://en.wikipedia.org/wiki/Tuckman%27s_stages_of_group_development

• Rich Sheridan on LinkedIn: https://www.linkedin.com/in/menloprez/

 • Menlo Innovations: https://menloinnovations.com/

• Drive: The Surprising Truth About What Motivates Us: https://www.amazon.com/Drive-Surprising-Truth-About-Motivates/dp/1594484805

• Toyota Kata: Managing People for Improvement, Adaptiveness and Superior Results: https://www.amazon.com/Toyota-Kata-Managing-Improvement-Adaptiveness/dp/0071635238

• Paulo Freire: https://en.wikipedia.org/wiki/Paulo_Freire

• Jon Walker on LinkedIn: https://www.linkedin.com/in/jwalker/

• Managing Corporate Lifecycles: https://www.amazon.com/Managing-Corporate-Lifecycles-Ichak-Adizes/dp/9381860548

• The Adizes Institute: https://www.adizes.com/

• John Cutler on Lenny’s Podcast: https://www.lennyspodcast.com/what-differentiates-the-highest-performing-product-teams-john-cutler-amplitude-the-beautiful-mes/

• Co-Active Training Institute: https://coactive.com/

• Co-Active Coaching: The proven framework for transformative conversations at work and in life: https://www.amazon.com/Co-Active-Coaching-Fourth-transformative-conversations/dp/1473674980

• Creating Intelligent Teams: https://www.amazon.com/Creating-Intelligent-teams-Anne-R%C3%B8d/dp/186922583X

• The Surprising Power of Liberating Structures: Simple Rules to Unleash a Culture of Innovation: https://www.amazon.com/Surprising-Power-Liberating-Structures-Innovation/dp/0615975305

• Facilitator’s Guide to Participatory Decision-Making: https://www.amazon.com/Facilitators-Participatory-Decision-Making-Jossey-bass-Management/dp/1118404955

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

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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.

Ethan Evans is a writer, career coach, course instructor, and retired VP at Amazon. During his 15 years at Amazon, he helped invent Prime Video, Amazon Video, the Amazon Appstore, Prime Gaming (formerly Twitch Prime), and Twitch Commerce. Prior to Amazon, Ethan spent 12 years in technical leadership roles at several East Coast startups. He writes a newsletter, Level Up, which publishes candid career advice and has a growing community of ambitious professionals to connect with. Ethan also offers a range of Leadership Development Courses via live online classes and on-demand courses. In this episode, we discuss:

• The Magic Loop framework: a five-step process to grow your career

• A handful of reasons why people get stuck in their career growth

• Advice on how to break out of a career plateau

• How to cultivate inventiveness in your work

• How to stand out in interviews

• A personal story of failing Jeff Bezos and lessons learned

• Contrarian opinions on the return-to-office movement and doing business on a handshake

—

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Find the full transcript at: https://www.lennysnewsletter.com/p/taking-control-of-your-career-ethan

—

Where to find Ethan Evans:

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

• Substack: https://levelupwithethanevans.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) Ethan’s background

(04:25) The Magic Loop

(08:31) The goal of the Magic Loop

(10:59) Clarifications on the framework

(12:46) Success stories

(17:22) The importance and effectiveness of the Magic Loop

(19:01) A quick summary of the steps in the Magic Loop

(21:46) What if you’re not pursuing a promotion?

(23:09) How to break out of a career plateau

(28:52) How to become systematically inventive

(36:04) Interview advice and how to stand out

(40:43) A story of failing Jeff Bezos

(50:31) Lessons learned from that failure

(57:30) What Ethan would have done differently

(01:00:35) Amazon’s leadership principles

(01:08:52) Contrarian corner: Returning to the office vs. staying remote

(01:10:39) Contrarian corner: Doing business on a handshake

(01:11:52) Lightning round

—

Referenced:

• The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop

• SDE levels: https://www.masaischool.com/blog/understanding-sde-levels-sde-1-vs-sde-2-vs-sde-3-differences/

• What Got You Here Won’t Get You There: How Successful People Become Even More Successful: https://www.amazon.com/What-Got-Here-Wont-There/dp/1401301304

• Thomas Edison’s quote: https://www.brainyquote.com/quotes/thomas_a_edison_109928

• Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• Jeff Wilke on X: https://twitter.com/jeffawilke

• Andy Jassy on LinkedIn: https://www.linkedin.com/in/andy-jassy-8b1615/

• Werner Vogels on LinkedIn: https://www.linkedin.com/in/wernervogels/

• Amazon’s Silk browser explained: https://www.androidpolice.com/amazon-silk-browser-explainer/

• Chickens and pigs: https://www.scrum.org/resources/chickens-and-pigs

• 58% of tech employees experience imposter syndrome. Here’s how to overcome it: https://medium.com/wearefutureworks/58-of-tech-employees-experience-imposter-syndrome-heres-how-to-overcome-it-78172d8a2258

• Jeff Bezos to exec after product totally flopped: ‘You can’t, for one minute, feel bad’: https://www.cnbc.com/2020/05/22/jeff-bezos-why-you-cant-feel-bad-about-failure.html

• Amazon’s leadership principles: https://www.amazon.jobs/content/en/our-workplace/leadership-principles

• Sam Altman on X: https://twitter.com/sama

• Decisive: How to Make Better Choices in Life and Work: https://www.amazon.com/Decisive-Make-Better-Choices-Life/dp/0307956393

• Leadership and Self-Deception: Getting Out of the Box: https://www.amazon.com/Leadership-Self-Deception-Getting-Out-Box/dp/1523097809

• The Almanack of Naval Ravikant: A Guide to Wealth and Happiness: https://www.amazon.com/Almanack-Naval-Ravikant-Wealth-Happiness/dp/1544514212/

• Angel list: https://venture.angellist.com/naval/syndicate

• Naval Ravikant on X: https://twitter.com/naval

• 1923 on Paramount+: https://www.paramountplus.com/shows/1923/

• Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone

• Chuckit! dog toys: https://www.chuckit-toys.co.uk/

• Luke 12:48: https://law.utk.edu/2016/05/10/to-whom-much-is-given-much-will-be-required

• The Challenger space shuttle disaster: https://en.wikipedia.org/wiki/Space_Shuttle_Challenger_disaster

• Ethan’s popular course on Maven: https://maven.com/ethan-evans/break-through-to-executive

—

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.

Sam Schillace is deputy CTO and corporate vice president at Microsoft. Prior to working at Microsoft, Sam started a company called Writely, which was acquired by Google and became the foundation of what today is Google Docs. While at Google, Sam helped lead many of Google’s consumer products, including Gmail, Blogger, PageCreator, Picasa, Reader, Groups, and more recently Maps and Google Automotive Services. Sam was also a principal investor at Google Ventures, has founded six startups, and was the SVP of engineering at Box through their IPO. In this episode, we discuss:

• The journey of building Google Docs

• The importance of taking risks, embracing failure, and finding joy in your work

• The importance of asking “what if” questions vs. “why not”

• Why convenience always wins

• How, and why, Sam stays optimistic

• Inside Microsoft’s culture

• Why you should solve problems without asking for permission

• Early-career advice

• Why “pixels are free” and “bots are docs”

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Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-be-more-innovative-sam-schillace

—

Where to find Sam Schillace:

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

• Newsletter: https://sundaylettersfromsam.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) Sam’s background

(03:45) The first Google Docs file

(06:45) Disruptive innovation

(10:11) First-principles thinking

(11:00) Recognizing disruptive ideas

(13:17) Examples of first-principles thinking

(15:46) The power of optimism

(19:47) Sam’s motto: Get to the edge of something and f**k around

(21:53) User value and laziness

(24:31) People are lazy (and what to do about it)

(28:36) Building Google Docs

(31:06) The evolution of Google Docs

(37:15) Finding product-market fit

(39:52) The future of documents

(44:57) The value of playing with technology

(47:58) Taking risks and embracing failure

(49:21) Thinking in the future

(53:48) Finding joy in your work

(01:01:20) Just do the best you can

(01:02:34) The transformational power of AI

(01:09:27) Advice for approaching AI

(01:13:07) The culture at Microsoft

(01:16:51) Closing thoughts

(01:17:32) Lightning round

—

Referenced:

• Google Docs began as a hacked-together experiment, says creator: https://www.theverge.com/2013/7/3/4484000/sam-schillace-interview-google-docs-creator-box

• Edna Mode: https://disney.fandom.com/wiki/Edna_Mode

• Sergey Brin’s profile on Forbes: https://www.forbes.com/profile/sergey-brin/

• People Who Were No Smarter Than You: https://medium.com/thrive-global/people-who-were-no-smarter-than-you-4e1c88c3fee6

• Nat Torkington (O’Reilly Media): https://www.oreilly.com/people/nathan-torkington/

• How Tesla Has Shaken (Not Stirred) Established Carmakers—and Why It Really Matters: https://www.forbes.com/sites/jenniferdungs/2021/04/23/how-tesla-has-shaken-not-stirred-established-carmakersand-why-it-really-matters/

• First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles

• Ashton Tate: https://en.wikipedia.org/wiki/Ashton-Tate

• Learning by Doing: https://www.linkedin.com/pulse/learning-doing-sam-schillace

• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/

• How do we make sense of all of this?: https://sundaylettersfromsam.substack.com/p/how-do-we-make-sense-of-all-of-this

• Steve Newman on LinkedIn: https://www.linkedin.com/in/stevescalyr/

• Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-schmidt-02158951/

• Michael Arrington on X: https://twitter.com/arrington

• TechCrunch: https://techcrunch.com/

• “Hello, Computer” scene from Star Trek: https://www.youtube.com/watch?v=hShY6xZWVGE

• Writely—Process Words with your Browser: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

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

• This Quote from Seth Godin Could Change How You Think About Pursuing Your Passion: https://friedchickenandsushi.com/blog/2021/7/5/this-quote-from-seth-godin-could-change-how-you-think-about-pursuing-your-passion

• AI isn’t a feature of your product: https://sundaylettersfromsam.substack.com/p/ai-isnt-a-feature-of-your-product

• Introducing Gemini: our largest and most capable AI model: https://blog.google/technology/ai/google-gemini-ai/

• Invisible Cities: https://www.amazon.com/Invisible-Cities-Italo-Calvino/dp/0156453800

• The Wasp Factory: https://www.amazon.com/WASP-FACTORY-NOVEL-Iain-Banks/dp/0684853159

• Where Good Ideas Come From: The Natural History of Innovation: https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380/

• Slow Horses on Apple TV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Monarch: Legacy of Monsters on Apple TV+: https://tv.apple.com/us/show/monarch-legacy-of-monsters/umc.cmc.62l8x0ixrhyq3yaqa5y8yo7ew?mttn3pid

• Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

• 2023 Mustang Mach-E: https://www.ford.com/suvs/mach-e/

• Boccalone Salumeria (now closed) on X: https://twitter.com/boccalone

—

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.

Will Larson is Chief Technology Officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February. In our conversation, we discuss:

• Systems thinking: what it is and how to apply it

• Advice for product managers on fostering productive relationships with engineering managers

• Why companies should treat engineers like adults

• How to best measure developer productivity

• Writing and its impact on his career

• How to balance writing with a demanding job

• How to develop your company values

—

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—

Find the full transcript at: https://www.lennysnewsletter.com/p/the-engineering-mindset-will-larson

—

Where to find Will Larson:

• X: https://twitter.com/Lethain

• LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/

• Website: https://lethain.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) Will’s background

(04:12) Changes in the field of engineering

(06:27) We need to stop treating engineers like children

(08:32) Systems thinking

(13:23) Implementing systems thinking in hiring

(16:32) Engineering strategy

(20:21) Examples of engineering strategies

(25:08) How to get good at strategy

(26:48) The importance of writing about things that excite you

(32:40) The biggest risk to content creation is quitting too soon

(35:24) How to make time for writing

(37:41) Tips for aspiring writers

(41:18) Building productive relationships between product managers and engineers

(43:45) Giving the same performance rating to EMs and PMs

(48:24) Measuring engineering productivity

(55:53) Defining company values

(01:02:10) Failure corner: the Digg rewrite

(01:11:05) Will’s upcoming book, The Engineering Executive’s Primer

(01:12:04) Lightning round

—

Referenced:

• The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom

• Work on what matters: https://lethain.com/work-on-what-matters/

• Sheryl Sandberg to Harvard Biz Grads: “Find a Rocket Ship”: https://www.forbes.com/sites/kashmirhill/2012/05/24/sheryl-sandberg-to-harvard-biz-grads-find-a-rocket-ship/?sh=708c9a93b37a

• What Is Systems Thinking?: https://www.snhu.edu/about-us/newsroom/business/what-is-systems-thinking

• Introduction to systems thinking: https://lethain.com/systems-thinking/

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• Silent Spring: https://www.amazon.com/Silent-Spring-Rachel-Carson/dp/0618249060

• Writing an engineering strategy: https://lethain.com/eng-strategies/

• Carta: https://carta.com/

• Eric Vogl on LinkedIn: https://www.linkedin.com/in/ericvogl/

• Good Strategy/Bad Strategy: The difference and why it matters: https://www.amazon.com/Good-Strategy-Bad-difference-matters/dp/1781256179

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/

• Technology Strategy Patterns: Architecture as Strategy: https://www.amazon.com/Technology-Strategy-Patterns-Architecture/dp/1492040878/

• The Value Flywheel Effect: Power the Future and Accelerate Your Organization to the Modern Cloud: https://www.amazon.com/Value-Flywheel-Effect-Accelerate-Organization/dp/1950508579

• The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win: https://www.amazon.com/Phoenix-Project-DevOps-Helping-Business/dp/1942788290

• The Engineering Executive’s Primer: Impactful Technical Leadership: https://www.amazon.com/Engineering-Executives-Primer-Impactful-Leadership/dp/1098149483

• An Elegant Puzzle: Systems of Engineering Management: https://press.stripe.com/an-elegant-puzzle

• Staff Engineer: Leadership beyond the management track: https://www.amazon.com/Staff-Engineer-Leadership-beyond-management-ebook/dp/B08RMSHYGG

• Gergely Orosz’s newsletter: https://blog.pragmaticengineer.com/author/gergely/

• Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer): https://www.lennyspodcast.com/videos/leaving-big-tech-to-build-the-1-technology-newsletter-gergely-orosz-the-pragmatic-engineer/

• The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo): https://www.lennyspodcast.com/videos/the-art-of-product-management-shreyas-doshi-stripe-twitter-google-yahoo/

• Henry Ward on LinkedIn: https://www.linkedin.com/in/heward/

• Vrushali Paunikar on LinkedIn: https://www.linkedin.com/in/vrushali-paunikar/

• Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339

• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennyspodcast.com/how-to-measure-and-improve-developer-productivity-nicole-forsgren-microsoft-research-github-goo/

• DORA: https://dora.dev/

• Setting engineering org values: https://lethain.com/setting-engineering-org-values/

• Digg: https://digg.com/

• Kevin Rose on LinkedIn: https://www.linkedin.com/in/kevinrose/

• Digg’s v4 launch: an optimism born of necessity: https://lethain.com/digg-v4/

• Dash Gopinath on LinkedIn: https://www.linkedin.com/in/dashgopinath/

• Rich Schumacher on LinkedIn: https://www.linkedin.com/in/richschumacher/

• The ALL NEW Don’t Think of an Elephant!: Know Your Values and Frame the Debate: https://www.amazon.com/ALL-NEW-Dont-Think-Elephant-ebook/dp/B00NP9LHFA

• Top Chef on Peacock: https://www.peacocktv.com/watch-online/tv/top-chef/5172289448907967112

• Hard to work with: https://lethain.com/hard-to-work-with/

—

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.

Judd Antin has spent 15 years leading research and design teams at companies like Yahoo, Meta, and Airbnb. His direct reports have gone on to lead user research at Figma, Notion, Slack, Robinhood, Duolingo, AllTrails, and more. In our conversation, we unpack the transformation that the user-research field is experiencing. Specifically:

• Where user research went wrong over the past decade

• The three types of research—macro, middle-range, and micro—and the purpose of each

• How to effectively integrate researchers into the product development process

• The “user-centered performance” phenomenon and why it’s a waste of time

• Common tropes about PMs, from researchers

• The ideal ratio of researchers in a company

• Why Judd says NPS is useless, and what to use instead

—

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Find the full transcript at: https://www.lennysnewsletter.com/p/the-ux-research-reckoning-is-here

—

Where to find Judd Antin:

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

• Website: https://juddantin.com/

• Blog: https://medium.com/onebigthought

—

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) Judd’s background

(04:16) Critiques and responses to Judd’s post “The UX Research Reckoning Is Here”

(07:33) The state of user research

(08:53) Macro, middle-range, and micro research

(14:05) What teams get wrong when it comes to research

(15:46) The importance of integrating research from the beginning

(17:30) Traits of great researchers

(19:53) Advice for evaluating user researchers

(21:10) Balancing business and product focus

(23:55) User-centered performance

(26:42) The role of intuition in product development

(30:15) Checking your gut instincts

(32:54) Common tropes about PMs, from researchers

(41:02) A/B testing vs. user research

(43:15) Hindsight bias and narrative fallacy

(44:55) Making recommendations based on research

(47:26) Advice for teams on how to leverage researchers

(51:18) How product managers can be better partners to user researchers

(56:53) The ideal ratio of researchers in a company

(59:43) Empowering user researchers to drive impact

(01:03:39) The limitations of NPS as a metric

(01:06:48) The risks of dogfooding

(01:08:51) Lightning round

—

Referenced:

• Matt Gallivan on LinkedIn: https://www.linkedin.com/in/mattgallivan/

• Janna Bray on LinkedIn: https://www.linkedin.com/in/janna-bray-a4046a25/

• Celeste Ridlen on LinkedIn: https://www.linkedin.com/in/celesteridlen/

• Rebecca Gray on LinkedIn: https://www.linkedin.com/in/rebeccagray2/

• Hannah Pileggi on LinkedIn: https://www.linkedin.com/in/hannah-pileggi-43169314/

• Louise Beryl on LinkedIn: https://www.linkedin.com/in/louise-beryl-13225833/

• The UX Research Reckoning Is Here: https://medium.com/onebigthought/the-ux-research-reckoning-is-here-c63710ea4084

• The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom

• Cognitive biases: https://en.wikipedia.org/wiki/List_of_cognitive_biases

• IDEO design thinking: https://designthinking.ideo.com/

• Everything Is Obvious: How Common Sense Fails Us: https://www.amazon.com/Everything-Obvious-Common-Sense-Fails/dp/0307951790

• Patrick Collison’s tweet: https://twitter.com/patrickc/status/1443215022029619200?lang=en

• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

• Brian Chesky on Lenny’s Podcast: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• NPS: https://en.wikipedia.org/wiki/Net_promoter_score

• What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat/

• Michael Murakami on LinkedIn: https://www.linkedin.com/in/michaelhmurakami/

• Bad Leadership: What It Is, How It Happens, Why It Matters: https://www.amazon.com/Bad-Leadership-Happens-Matters-Common/dp/1591391660

• Demon Copperhead: https://www.amazon.com/Demon-Copperhead-Novel-Barbara-Kingsolver/dp/0063251922

• All Systems Red: The Murderbot Diaries: https://www.amazon.com/All-Systems-Red-Murderbot-Diaries/dp/0765397536

• The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Belay glasses: https://www.amazon.com/Belay-Glasses-Climbing-Comfortable-Sturdy/dp/B08GSBYDKQ/

• Epictetus: Control What You Can—Especially Yourself: https://www.shortform.com/blog/epictetus-control/

• The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change: https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519

—

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.

Nir Eyal is the author of two best-selling books, Hooked: How to Build Habit-Forming Products and Indistractable: How to Control Your Attention and Choose Your Life. He writes, consults, and teaches at the intersection of psychology, technology, and business. His books have sold over 1 million copies in more than 30 languages; he has taught at Stanford’s Graduate School of Business and its Design School; and he has started and sold two startups since 2003. In our conversation, we discuss:

• Strategies for becoming less distractible and improving focus

• The difference between distraction and “traction”

• Reactive work vs. reflexive work and why you should book time in your calendar

• The 10-minute rule to overcome internal triggers and stay focused

• The problem with to-do lists, and what to do instead

• The value of creating a timebox schedule that aligns with personal values and priorities

• The use of pacts as a last line of defense against distraction

• How to develop a high-agency mindset

• Advice for leaders on helping employees improve focus in the workplace

—

Brought to you by Vanta—Automate compliance. Simplify security | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Teal—Your personal career growth platform

—

Find the full transcript at: https://www.lennysnewsletter.com/p/strategies-for-becoming-less-distractible

—

Where to find Nir Eyal:

• X: https://twitter.com/nireyal

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

• Website: https://www.nirandfar.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) Nir’s background

(04:20) How to become less distractible

(07:43) Understanding distraction and traction

(12:52) The four steps to becoming indistractable

(13:53) Mastering internal triggers

(18:49) Surfing the urge with a 10-minute timer

(23:20) Making time for traction with a timebox schedule

(25:02) How to turn your values into time

(28:36) Booking deep work time

(29:22) Making pacts to prevent distraction

(31:00) The problem with to-do lists

(34:31) The drawback of deadlines

(36:08) Distraction is an emotion regulation problem

(39:54) Hacking back external triggers

(45:03) Preventing distraction with pacts

(48:18) Specific tools to hold you accountable

(53:42) Managing emotions and discomfort

(56:37) Taking responsibility and being high-agency

(01:00:09) Becoming indistractable at work

(01:05:04) Schedule syncing to align with managers

(01:09:36) We are not as hooked on technology as people think

(01:16:00) Life purpose and personal responsibility

(01:17:38) Lightning round

—

Referenced:

• Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/Indistractable-Control-Your-Attention-Choose/dp/194883653X

• Hooked: How to Build Habit-Forming Products: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/1591847788

• Dorothy Parker’s quote: https://twitter.com/nireyal/status/1472280598723108866

• “Writing is bleeding” quote: https://www.hemingwaysociety.org/quotation-controversy-writing-and-bleeding

• The Pomodoro Technique Explained: https://www.forbes.com/sites/bryancollinseurope/2020/03/03/the-pomodoro-technique/

• Timeboxing: Why It Works and How to Get Started in 2024: https://www.nirandfar.com/timeboxing/

• Using your working time well - Issue 22: https://www.lennysnewsletter.com/p/time-management-issue-22

• All-In podcast: https://www.allinpodcast.co/

• Nir’s post about “the planning fallacy”: https://www.linkedin.com/posts/nireyal_why-do-tasks-always-seem-to-take-longer-than-activity-7137440438939959297-XIUB/

• How the Ancient Greeks Beat Distraction: https://www.nirandfar.com/tantalizing-distractions/

• Jeremy Bentham: https://iep.utm.edu/jeremy-bentham

• An overview of Sigmund Freud’s pleasure principle: https://www.sciencedirect.com/topics/nursing-and-health-professions/pleasure-principle

• The Matrix “There is no spoon” scene: https://www.youtube.com/watch?v=uAXtO5dMqEI

• Outlet timer: https://www.amazon.com/Century-Indoor-24-Hour-Mechanical-Outlet/dp/B01LPSGBZS

• Forest app: https://www.forestapp.cc/

• Focusmate: https://www.focusmate.com/

• Have We Been Thinking About Willpower the Wrong Way for 30 Years?: https://hbr.org/2016/11/have-we-been-thinking-about-willpower-the-wrong-way-for-30-years

• We Need Social Antibodies to Fight the Disease of Distraction: https://nireyal.medium.com/we-need-social-antibodies-to-fight-the-disease-of-distraction-51f9187be016

• The Mere Presence of Your Smartphone Reduces Brain Power, Study Shows: https://news.utexas.edu/2017/06/26/the-mere-presence-of-your-smartphone-reduces-brain-power

• Leading in Tough Times: HBS Faculty Member Amy C. Edmondson on Psychological Safety: https://www.hbs.edu/recruiting/insights-and-advice/blog/post/leading-in-tough-times

• If Tech Is So Distracting, How Do Slack Employees Stay So Focused?: https://www.nirandfar.com/slack-use/

• Managing up: https://www.lennysnewsletter.com/p/managing-up

• Duolingo: https://www.duolingo.com/

• FitBot: https://www.fitbotapp.com/

• Paulo Coelho’s quote: https://twitter.com/paulocoelho/status/416264984188825600

• 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

• The Experience Machine: How Our Minds Predict and Shape Reality: https://www.amazon.com/Experience-Machine-Minds-Predict-Reality/dp/1524748455

• Empire of the Sun on Prime Video: https://www.amazon.com/Empire-Sun-Christian-Bale/dp/B001N3JY82

• Sesame grinder: https://www.miyacompany.com/450-014-450-014

• Muji pens: https://www.muji.us/collections/pen-pencils

—

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.

Sarah Tavel is a General Partner at Benchmark and sits on the boards of Chainalysis, Hipcamp, Rekki, Cambly, and Medely. She is a founding member of All Raise, the nonprofit organization working to accelerate the success of women in the venture-capital and VC-backed startup ecosystem. Before Benchmark, Sarah was a partner at Greylock Partners. She joined Pinterest in 2012 as their first PM and launched their first search and recommendations features. She also led three acquisitions as she helped the company scale through a period of hypergrowth. In this episode, we discuss:

Sarah’s Hierarchy of Engagement framework for growing a consumer startup

• The three levels of the Hierarchy of Engagement: core action, retention, and self-perpetuation

• The importance of measuring cohorts and maintaining focus on the core action

• Examples of core user actions from Pinterest and YouTube

Sarah’s Hierarchy of Marketplaces framework for building a marketplace startup

• The three vectors of growth for dominating a marketplace

• Advice on “tipping the marketplace” and ultimately dominating the market

• The value of focusing on a constrained market

• How to avoid disruption

—

This entire episode is brought to you by Gelt—Redefine your approach to taxes.

—

Find the full transcript at: https://www.lennysnewsletter.com/p/the-hierarchy-of-engagement-sarah

—

Where to find Sarah Tavel:

• X: https://twitter.com/sarahtavel

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

• Substack: https://www.sarahtavel.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) Sarah’s background

(03:33) Framework 1: The Hierarchy of Engagement

(06:03) Level 1: Core action

(10:33) Level 2: Retention

(14:00) Level 3: Self-perpetuation

(19:32) The importance of focus

(23:54) The challenge of anonymity

(26:04) Advice for founders who want to increase retention

(29:34) What founders often get wrong

(31:43) Examples of core actions

(37:37) Finding your North Star Metric

(38:12) Who should use the Hierarchy of Engagement framework

(38:54) The Hierarchy of Marketplaces framework

(46:09) Level 1: Focus on a constrained opportunity

(50:19) Sarah’s “happy GMV” and “minimum viable happiness” concepts

(54:47) Thumbtack: a counterexample to this approach

(56:36) Signs you’re ready to move to level 2

(58:06) Level 2: Tipping the marketplace

(01:04:15) Tipping loops

(01:10:53) Not all markets are susceptible to tipping

(01:15:55) The challenge of homogeneity in B2B marketplaces

(01:20:29) Signs you’re tipping successfully

(01:21:43) Level 3: Dominating the market

(01:28:29) The opportunity in underestimated markets

(01:30:11) The challenges of chasing GMV and losing focus

(01:36:36) Recognizing currents and momentum in the market

(01:39:20) You can never rest on your laurels

(01:41:03) How to apply these frameworks outside of marketplaces

(01:42:57) Three ways to find marketplace opportunity

(01:45:10 ) Lightning round

—

Referenced:

• Hierarchy of Engagement, Expanded: https://sarahtavel.medium.com/the-hierarchy-of-engagement-expanded-648329d60804

• Pinterest: https://www.pinterest.com/

• Evernote: https://evernote.com/

• Notion: https://www.notion.so/

• Houseparty app: https://en.wikipedia.org/wiki/Houseparty_(app)

• Clubhouse: https://www.clubhouse.com/

• How to price your product | Naomi Ionita (Menlo Ventures): https://www.lennyspodcast.com/how-to-price-your-product-naomi-ionita-menlo-ventures/

• TikTok: https://www.tiktok.com/

• Lessons on building a viral consumer app: The story of Saturn: https://www.lennysnewsletter.com/p/lessons-on-building-a-viral-consumer

• Saturn: https://www.joinsaturn.com/

• What happened to Secret?: https://www.failory.com/cemetery/secret

• How to determine your activation metric: https://www.lennysnewsletter.com/p/how-to-determine-your-activation

• Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/

• 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/

• Engagement Hierarchy: Core Actions: https://sarahtavel.medium.com/engagement-hierarchy-core-actions-dd4f72042100

• Choosing Your North Star Metric: https://www.lennysnewsletter.com/p/choosing-your-north-star-metric

• Hierarchy of Marketplaces: https://sarahtavel.medium.com/the-hierarchy-of-marketplaces-introduction-and-level-1-983995aa218e

• Mike Williams on LinkedIn: https://www.linkedin.com/in/yoroomie/

• Everything Marketplaces: https://www.everythingmarketplaces.com/

• Fabrice Grinda on LinkedIn: https://www.linkedin.com/in/fabricegrinda/

• OLX: https://www.olx.com/

• DoorDash Loves the ’Burbs as Much as You Do: https://www.wsj.com/articles/doordash-loves-the-burbs-as-much-as-you-do-11605618001

• Thumbtack: https://www.thumbtack.com/

• NPS: https://en.wikipedia.org/wiki/Net_promoter_score

• Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/

• Rekki: https://rekki.com/

• Ronen Givon on LinkedIn: https://www.linkedin.com/in/ronen-givon-535b2514

• Hipcamp: https://www.hipcamp.com/

• Demand driving supply: The little-understood growth loop behind a surprising number of iconic billion-dollar companies: https://www.lennysnewsletter.com/p/demand-driving-supply-marketplaces

• Inside the Revolution at Etsy: https://www.nytimes.com/2017/11/25/business/etsy-josh-silverman.html

• Faire: https://www.faire.com/

• Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/

• Mechanical Turk: https://www.mturk.com/

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/

• Rippling: https://www.rippling.com/

• “White Space” for Building a Marketplace: How to Find Your Competition’s Vulnerabilities—and Capitalize: https://sarahtavel.medium.com/white-space-for-building-a-marketplace-how-to-find-your-competitions-vulnerabilities-and-79674aa4d399

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935

• The Five Temptations of a CEO: https://www.amazon.com/Five-Temptations-CEO-Anniversary-Leadership/dp/0470267585

• The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756

• Tesla: https://www.tesla.com/

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• What Is A Good Activation Rate: https://www.lennysnewsletter.com/p/what-is-a-good-activation-rate

—

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.

Christian Idiodi is a partner at Silicon Valley Product Group. After a long product career and founding multiple companies, Christian now spends his time working closely with product leaders at companies big and small to implement and improve their discipline of product management. In today’s episode, we discuss:

• Why there’s often a negative perception of product managers, and how we can fix this

• The four attributes of a product manager’s job: value, usability, viability, and feasibility

• The power of finding reference customers

• How Christian developed a process for high-volume hiring to help companies like McDonald’s and Starbucks

• Tactical tips for coaching, building relationships, and building trust as a leader

—

Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Vanta—Automate compliance. Simplify security | Teal—Your personal career growth platform

—

Find the full transcript at: https://www.lennysnewsletter.com/p/the-essence-of-product-management

—

Where to find Christian Idiodi:

• X: https://twitter.com/CIdiodi

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

• Website: 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) Christian’s background

(03:56) The negative perception of product managers

(07:58) How to become a PM people want to work with

(11:30) The definition of a product manager

(14:46) Where new PMs fail

(16:59) Reference customers: what they are and why they are so important

(24:05) A quick summary of how to build a product that people want and love

(26:44) How to determine product-market fit

(29:54) The benefits of this approach

(34:11) Real examples of using reference customers

(40:06) Doing things that don’t scale

(48:40) How to get better at coaching and build trust with leaders

(55:53) The fastest way to build trust

(01:00:01) What to do in the absence of good coaching

(01:02:51) How to get into product management

(01:04:16) The pitfalls of early promotions

(01:11:11) How to train someone for a promotion before giving the promotion

(01:13:30) How to find a good coach

(01:14:40) Christian’s product work in Africa

(01:21:22) The importance of passion and empathy in product work

(01:22:54) Lightning round

—

Referenced:

• Marty Cagan on LinkedIn: https://www.linkedin.com/in/cagan/

• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/

• Silicon Valley Product Group: https://www.svpg.com/

• Enhanced Product Discovery by SVPG Partner Christian Idiodi at Lean Product Meetup: https://www.youtube.com/watch?v=eQKaFEqhiqc

• Geoffrey Moore’s technology adoption curve: https://fourweekmba.com/technology-adoption-curve/

• Stripe: https://stripe.com/

• Building a culture of excellence | David Singleton (CTO of Stripe): https://www.lennyspodcast.com/building-a-culture-of-excellence-david-singleton-cto-of-stripe/

• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennyspodcast.com/building-beautiful-products-with-stripes-head-of-design-katie-dill-stripe-airbnb-lyft/

• Rippling: https://www.rippling.com/

• Snagajob: https://www.snagajob.com/

• Howard Schultz on LinkedIn: https://www.linkedin.com/in/howardschultz/

• Tesla portable charger: https://shop.tesla.com/product/mobile-connector

• Innovate Africa Foundation: https://www.innovateafrica.io/about/

• Inspire Africa Conference: https://www.inspireafricaconference.com/

• Inspired: How to Create Tech Products Customers Love: https://www.svpg.com/books/inspired-how-to-create-tech-products-customers-love-2nd-edition/

• Empowered: Ordinary People, Extraordinary Products: https://www.svpg.com/books/empowered-ordinary-people-extraordinary-products/

• Transformed: Moving to the Product Operating Model: https://www.svpg.com/books/transformed-moving-to-the-product-operating-model/

• Succession on HBO: https://www.hbo.com/succession

• Billions on Showtime: https://www.sho.com/billions

• Real sports app: https://www.realapp.link/

—

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.

Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss:

• Why he and his team prioritize profit above all else

• The unexpected challenges with raising venture capital

• The “Shape Up” framework for building products

• Why, and how, to foster a gut-driven culture

• Jason’s thoughts on why work should not feel like war

• Advice for starting a bootstrapped business

• The philosophy behind Once, 37signals’s new line of software products

—

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—

Find the full transcript at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

—

Where to find Jason Fried:

• X: https://twitter.com/jasonfried

• LinkedIn: https://www.linkedin.com/in/jason-fried/

• Email: jason@hey.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

(03:49) The success of 37signals

(06:46) When raising money makes sense

(09:58) The power of small teams

(13:55) Defining success and goals

(17:08) Playing “infinite games” in life

(20:11) Starting a business vs. staying in business

(22:13) Lessons from 25 years in business

(27:28) Venture scale vs. bootstrapping

(30:30) Choosing the right path for your business

(33:19) The “Shape Up” framework

(37:59) The drawback of promises

(39:56) Adopting a new way of working

(41:36) The two-week cooldown

(43:53) Trusting intuition and gut

(46:41) Creating a gut-driven culture

(49:44) What Jason looks for in new hires

(56:19) Advice on making changes and adapting

(01:00:06) What Jason has changed his mind about

(01:02:33) Planning in 6-week stretches and figuring it out as you go

(01:06:43) Being proud of the work you do

(01:09:05) Jason’s thoughts on why work should not feel like war

(01:11:31) Advice for starting a bootstrapped business

(01:14:33) You must be at peace with the worst that can happen

(01:15:42) The benefits of bootstrapping

(01:19:11) The value of constraints in business

(01:22:00) Jason’s philosophy: “Just keep making great s**t”

(01:23:19) Once, 37signals’s new line of software products

(01:26:33) The philosophy behind Once

(01:35:47) Closing thoughts

(01:37:23) Lightning round

—

Referenced:

• 37 Signals: https://www.smartsheet.com/

• Basecamp: https://basecamp.com/

• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713/

• Ingram Micro: https://www.ingrammicro.com/

• Once: https://once.com/

• Basecamp’s Shape Up framework: https://basecamp.com/shapeup

• Hill charts: https://basecamp.com/features/hill-charts

• Jason Fried’s quote about long-term business planning: https://medium.com/@farkhan569/unless-you-are-a-fortune-teller-long-term-business-planning-is-a-fantasy-jason-fried-quote-a69e8778e9c4

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• Matt Mullenweg on X: https://twitter.com/photomatt

• Leo Polovets on X: https://twitter.com/lpolovets

• HEY: https://www.hey.com/

• Redefining success, money, and belonging | Paul Millerd (The Pathless Path): https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/

• It Doesn’t Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780

• Squarespace: https://www.squarespace.com/

• Stoic negative visualization: https://dailystoic.com/premortem/

• Linear: https://linear.app/

• Peter Rahal on LinkedIn: https://www.linkedin.com/in/peter-rahal-037bba43/

• RXBAR: https://www.rxbar.com/en_US/home.html

• Jason’s LinkedIn post: https://www.linkedin.com/posts/jason-fried_just-keep-making-great-s**t-keep-your-costs-activity-7130978623523614720-VBGX/?trk=public_profile

• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413

• Hell Yeah or No: What’s Worth Doing: https://www.amazon.com/Hell-Yeah-No-whats-worth/dp/1988575117/

• Home-Made: Contemporary Russian Folk Artifacts: https://www.amazon.com/Home-Made-Contemporary-Russian-Folk-Artifacts/dp/0955006139

• Oppenheimer: https://www.oppenheimermovie.com/

• Tom Petty’s “Crawling Back to You” on Spotify: https://open.spotify.com/track/1JenqZNMU6unIwVWmoP3J0

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

—

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.

Matthew Dicks is a best-selling author, columnist, blogger, podcaster, playwright, and teacher. He wrote my all-time favorite book on storytelling, Storyworthy. He is an elementary school teacher by day and by night teaches storytelling and public speaking to individuals, corporations, universities, religious institutions, and school districts around the world. He’s taught storytelling at Yale, MIT, Harvard, and Purdue, along with Amazon, Salesforce, Slack, Lego, and others. In this conversation, Matthew shares insights and techniques for effective storytelling, including:

• The benefits of good storytelling in business

• The five-second moment and why it’s so important

• Why you should start every story at the end

• How to build a vault of stories that can be deployed in business situations

• Tips on how to be funnier

• His life-changing “Homework for Life” practice

• Advice for dealing with nervousness in public speaking

• The power of saying yes

—

Brought to you by OneSchema—Import CSV data 10x faster | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door | Vanta—Automate compliance. Simplify security.

—

Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew

—

Where to find Matthew Dicks:

• Website: https://matthewdicks.com/

• X: https://twitter.com/MatthewDicks

• LinkedIn: https://www.linkedin.com/in/matthew-dicks-84a95711/

• YouTube: https://www.youtube.com/channel/UC4K0fcEJkzJLso5h6CN00LQ

• Storyworthy: https://www.storyworthymd.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) Matthew’s background

(04:27) The five-second moment

(10:29) Knowing the ending

(14:28) The importance of including a transformation

(15:59) The dinner test

(18:19) You can’t tell someone else’s story

(20:24) Vacation stories

(23:14) Adding stakes to the story

(25:12) The power of surprise

(29:20) The benefits of storytelling in business

(32:20) An example of adding stakes

(34:02) Storytelling in the workplace

(44:29) Using personal inventory to make stories relatable

(48:46) Four ways to keep people listening

(50:52) Using humor in business storytelling

(53:09) Advice for adding humor

(58:43) An example of how storytelling helped a biotech company sell product

(1:02:06) Advice for people who don’t want to become storytellers

(1:06:35) The power of “Homework for Life”

(01:15:26) Practical tips for starting Homework for Life

(01:19:28) Dealing with nervousness in public speaking

(01:24:42) Preparing for a talk or presentation

(01:25:24) The power of saying yes

(01:30:55) Lightning round

—

Referenced:

• How ‘Star Wars’ answers our biggest religious questions: https://www.washingtonpost.com/posteverything/wp/2015/04/21/how-star-wars-answers-our-biggest-religious-questions/

• When Harry Met Sally on Prime Video: https://www.amazon.com/When-Harry-Sally-Billy-Crystal/dp/B001Q556QG

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennyspodcast.com/persuasive-communication-and-managing-up-wes-kao-maven-seth-godin-section4/

• Kurt Vonnegut’s 8 Tenets of Storytelling: https://www.themarginalian.org/2012/04/03/kurt-vonnegut-on-writing-stories/

• Vertigo on Prime Video: https://www.amazon.com/Vertigo-James-Stewart/dp/B000I9YLXU

• Ocean’s Eleven on Prime Video: https://www.amazon.com/Oceans-Eleven-George-Clooney/dp/B001EBV0JE

• David Mamet | JCCSF: https://www.youtube.com/watch?v=aZOT1jCHfhI

• Pulp Fiction on Prime Video: https://www.amazon.com/Pulp-Fiction-John-Travolta/dp/B005T3AX6E

• Charity Thief: Boston Moth StorySLAM: https://www.youtube.com/watch?v=YjrlGhAB4a4

• Boris Levin on LinkedIn: https://www.linkedin.com/in/boris-levin-ab95404/

• Masha Reutovski on LinkedIn: https://www.linkedin.com/in/masha-reutovski/

• Top Three Steve Jobs Speeches: https://www.pcworld.com/article/482269/top_three_steve_jobs_speeches.html

• The Javits Center: https://www.javitscenter.com/

• Stranger Things on Netflix: https://www.netflix.com/title/80057281

• 1989 (Taylor’s Version) on Spotify: https://open.spotify.com/album/64LU4c1nfjz1t4VnGhagcg

• Classic Sesame Street—one of these things is not like the other: https://www.youtube.com/watch?v=gCxrkl2igGY

• Homework for Life: https://matthewdicks.com/homework-for-life/

• Homework for Life | Matthew Dicks | TEDxBerkshires: https://www.youtube.com/watch?v=x7p329Z8MD0

• Seth Meyers: https://en.wikipedia.org/wiki/Seth_Meyers

• David Sedaris on MasterClass: https://www.masterclass.com/classes/david-sedaris-teaches-storytelling-and-humor

• Happy-Go-Lucky: https://www.amazon.com/Happy-Go-Lucky-David-Sedaris/dp/0316392456

• A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

• New York Comedy Festival: https://nycomedyfestival.com/

• In the Heart of the Sea: The Tragedy of the Whaleship Essex: https://www.amazon.com/Heart-Sea-Tragedy-Whaleship-Essex/dp/0141001828

• The Tale of Despereaux: https://www.amazon.com/Tale-Despereaux-Being-Princess-Thread/dp/0763680893

• I’ll Show Myself Out: Essays on Midlife and Motherhood: https://www.amazon.com/Ill-Show-Myself-Out-Motherhood/dp/0062981595

• You’ll Grow Out of It: https://www.amazon.com/Youll-Grow-Out-Jessi-Klein/dp/1455531200

• David Sedaris books: https://www.amazon.com/stores/David-Sedaris/author/B000AQ3YUW

• Sure, I’ll Join Your Cult: A Memoir of Mental Illness and the Quest to Belong Anywhere: https://www.amazon.com/Sure-Ill-Join-Your-Cult/dp/1982168560

• The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Barbie: https://www.barbie-themovie.com/

• Krinner tree genie on Amazon: https://www.amazon.com/Krinner-Genie-Christmas-Stand-Small-Green/dp/B081D78FTP

• Power Pod: https://powerpodshop.com/

• Nostalgia hotdog toaster: https://www.amazon.com/Nostalgia-HDT600RETRORED-Pop-Up-Toaster-Retro/dp/B005Q8X6IO

—

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.

In this special compilation episode, we delve into failure—an overlooked source of wisdom. From freezing onstage in front of thousands of people, to coworkers staging an intervention, to huge product investments that went to zero, we’ve pulled our favorite stories of failure from 100+ podcast episodes. I hope these stories serve as a gentle nudge to view failure not as a setback but as a crucial detour toward growth.

—

Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps | Eppo—Run reliable, impactful experiments

—

Find the full transcript at: https://www.lennysnewsletter.com/p/failure

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, you’ll hear from:

(00:00) Lenny: Why I’m focusing on failure

(03:25) Katie Dill: The single meeting that changed how Katie leads forever

(08:03) Paul Adams: Freezing onstage in front of thousands of people

(18:38) Tom Conrad: Lessons from Pets.com and Quibi—two of the most famous product disasters of all time

(33:19) Sri Batchu: When you fail, make sure you fail conclusively

(39:00) Jiaona Zhang (JZ): One of the biggest product misses at Airbnb

(44:32) Gina Gotthilf: Everyone has an “A side” and a “B side,” and we should all share our B sides more

(57:57) Maggie Crowley: Her favorite interview question about failure, and lessons from a personal failure

(1:00:33) Thanks for listening

—

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.

Kim Scott is the author of Radical Candor, currently the #1 most recommended book on this podcast. The book has sold over 1 million copies and has been translated into 23 languages. Before writing, Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was also a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google. This spring she’ll be launching Radical Respect, which she considers to be a prequel to Radical Candor. In today’s conversation, we go deep on Kim’s popular framework, including:

• What separates radical candor and obnoxious aggression

• Tactical advice on delivering constructive feedback

• How well-meaning empathy can become ruinous

• Strategies for effectively soliciting and responding to feedback

• The importance of having regular career conversations

• The false dichotomy of a good leader versus a kind person

• A sneak peek into Radical Respect

—

Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams

—

Find the full transcript at: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

—

Where to find Kim Scott:

• X: https://twitter.com/kimballscott

• LinkedIn: https://www.linkedin.com/in/kimm4/

• Website: https://www.radicalcandor.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) Kim’s background

(03:13) A brief overview of Radical Candor

(06:46) How people fail with ruinous empathy, manipulative insincerity, and obnoxious aggression

(08:37) The impact of radical candor on Kim’s life

(14:16) How to communicate feedback effectively

(20:34) A story illustrating the problem with ruinous empathy and manipulative insincerity

(27:50) How to get over the need to be liked

(31:31) How to have career conversations with your direct reports

(29:40) Reflections on how Kim handled an underperforming employee

(33:31) Best practices for soliciting feedback as a leader

(35:53) How to respond to feedback

(39:22) How often to ask for feedback

(41:48) Whether or not to accept “no feedback” as an answer

(50:48) Investing time in feedback

(54:04) How to ask for feedback as an employee

(57:42) Why obnoxious aggression is not the best way to deliver feedback

(1:01:23) A notable example of problematic management 

(1:03:43) Why context matters when diagnosing obnoxious aggression 

(1:07:39) Empathy is a good thing, but empathy can paralyze

(1:10:47) Reflections on the limitations of radical candor in a society riddled with biases 

(1:14:41) Kim’s new book, Radical Respect

(1:15:51) Tactical advice to get better at radical candor

(1:16:46) Lightning round

—

Referenced:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Radical Respect: How to Work Together Better: https://www.amazon.com/Radical-Respect-Work-Together-Better/dp/1250623766/

• The Office (American version) on Peacock: https://www.peacocktv.com/stream-tv/the-office

• Radical Candor diagram: https://www.radicalcandor.com/our-approach/

• Career conversation templates: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager/

• A behavioral scientist explains why we should reacquaint ourselves with the telephone: https://news.uchicago.edu/story/nicholas-epley-explains-why-phone-calls-can-connect-us-better-zoom

• How to get promoted: https://www.lennysnewsletter.com/p/how-to-get-promoted

• When They Win, You Win: Being a Great Manager Is Simpler Than You Think: https://www.amazon.com/When-They-Win-You-Manager/dp/1250279666

• Peter Kazanjy on X: https://twitter.com/Kazanjy

• Christa Quarles on LinkedIn: https://www.linkedin.com/in/christaquarles/

• Jason Rosoff on LinkedIn: https://www.linkedin.com/in/jason-r-rosoff/

• Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove

• Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

• Squid Game on Netflix: https://www.netflix.com/title/81040344

• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennyspodcast.com/leveraging-mentors-to-uplevel-your-career-jules-walter-youtube-slack/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239

• Bridgewater: https://www.bridgewater.com/

• The Fund: Ray Dalio, Bridgewater Associates, and the Unraveling of a Wall Street Legend: https://www.amazon.com/Fund-Bridgewater-Associates-Unraveling-Street/dp/1250276934/

• Tim Cook on X: https://twitter.com/tim_cook

• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281

• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennyspodcast.com/building-high-performing-teams-melissa-tan-webflow-dropbox-canva/

• Middlemarch: https://www.amazon.com/Middlemarch-Penguin-Classics-George-Eliot/dp/0141439548

• The Bluest Eye: https://www.amazon.com/Bluest-Eye-Vintage-International/dp/0307278441

• Song of Solomon: https://www.amazon.com/Song-Solomon-Toni-Morrison/dp/140003342X

• Orlando: https://www.amazon.com/Orlando-Biography-Virginia-Woolf/dp/015670160X

• The Color Purple: https://www.amazon.com/Color-Purple-Novel-Alice-Walker/dp/0143135694

• The Deptford Trilogy: Fifth Business; The Manticore; World of Wonders: https://www.amazon.com/Deptford-Trilogy-Business-Manticore-Wonders/dp/0140147551

• Grey’s Anatomy on Netflix: https://www.netflix.com/title/70140391

• My year of saying yes to everything: https://www.ted.com/talks/shonda_rhimes_my_year_of_saying_yes_to_everything

• Attitude: https://attitudeliving.com/collections/adult-hair-care

• Dostoevsky books: https://www.amazon.com/Fyodor-Dostoevsky-Books/s?k=Fyodor+Dostoevsky

—

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.

Anuj Rathi is the Chief Product and Marketing Officer at Jupiter Money, where he leads product management, marketing, design, growth, and analytics. Before Jupiter Money, Anuj served as the Senior Vice President of Revenue and Growth at Swiggy, VP of Product at SnapDeal, a Senior PM at Walmart Labs and the first-ever PM at Flipkart. He’s also one of the most beloved and respected product leaders in India. In this episode, we discuss:

• How product management is different in India

• How to rethink your approach to new users

• How Anuj operationalizes the “working backwards” framework

• Why Anuj thinks PMs should be more full-stack than they are

• How to use Anuj’s “4BB” framework to get better at product strategy and prioritization

• Advice on developing innovative roadmap ideas

• The three essential skills of a successful PM

• Three reasons why leadership fails

• Why OKRs don’t work in marketplaces

—

Brought to you by Sanity—The most customizable content layer to power your growth engine | Vanta—Automate compliance. Simplify security | Wix Studio—The web creation platform built for agencies

—

Find the full transcript at: https://www.lennysnewsletter.com/p/the-full-stack-pm-anuj-rathi-swiggy

—

Where to find Anuj Rathi:

• X: https://twitter.com/anujrathi

• LinkedIn: https://www.linkedin.com/in/anujrathi1

—

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) Anuj’s background

(04:28) How product differs in India 

(08:34) When modern product thinking started to gain traction in India

(14:01) How Anuj thinks about new-user experiences

(15:07) Scott Belsky’s “lazy, vain, and selfish” framework 

(19:59) Why PMs must understand category consumers

(22:30) Anuj’s philosophy on the PM job

(23:59) How Anuj applies the working-backwards framework

(28:36) The importance of FAQs

(30:10) The full-stack PM mindset

(33:06) Anuj’s “show don’t tell” framework

(36:19) How to use the show-don’t-tell framework

(39:14) The impact of using this framework

(41:27) Anuj’s “4BB framework” for product strategy

(48:59) Contrarian corner

(50:49) Anuj’s “framework of 3” for great PMs

(52:34) How to develop grit and influence

(54:00) Three reasons why leaders fail 

(56:21) AI corner

(57:51) Lessons from building a successful marketplace

(1:02:19) How to balance and maintain stability on all sides of a marketplace

(1:07:48) Lightning round

—

Referenced:

• MakeMyTrip: https://www.makemytrip.com/

• Shaadi.com: https://www.shaadi.com/

• Bharat Matrimony: https://www.bharatmatrimony.com/

• Flipkart: https://www.flipkart.com/

• Ola: https://www.olacabs.com/mobile

• Swiggy: https://www.swiggy.com/

• Jio: https://www.jio.com/

• UPI: http://cashlessindia.gov.in/upi.html

• The First 15 Seconds by Scott Belsky: https://medium.com/positiveslope/the-first-15-seconds-9590d7dabc

• Jupiter: https://jupiter.money/

• How to get better at influence: https://www.lennysnewsletter.com/p/how-to-get-better-at-influence#

• Working Backwards: https://www.workingbackwards.com/

• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

• In Search of Greatness on Prime Video: https://www.amazon.com/Search-Greatness-Wayne-Gretzky/dp/B07P5X99P5

• Team Topologies: Organizing Business and Technology Teams for Fast Flow: https://www.amazon.com/Team-Topologies-Organizing-Business-Technology/dp/1942788819

• Conway’s Law: https://www.atlassian.com/blog/teamwork/what-is-conways-law-acmi

• Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): 

https://www.lennyspodcast.com/lessons-from-scaling-spotify-the-science-of-product-taking-risky-bets-and-how-ai-is-already-impac/

• Taobao: https://world.taobao.com/

• Alibaba: https://offer.alibaba.com/

• Working Backwards: https://www.amazon.com/Working-Backwards-PB/dp/1529033845

• How Brands Grow: What Marketers Don't Know: https://www.amazon.com/How-Brands-Grow-What-Marketers/dp/0195573560

• The Luxury Strategy: Break the Rules of Marketing to Build Luxury Brands: https://www.amazon.com/Luxury-Strategy-Break-Marketing-Brands/dp/0749464917

• The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office

• Rise: https://www.risescience.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.

Ebi Atawodi is Director of Product Management for the Creator Experience at YouTube, former Head of Product at Uber, and a former Director of Product (Payments and EMEA) at Netflix. Known for crafting a strong, unified vision, Ebi empowers her teams to achieve outsized outcomes. In today’s episode, we go deep into vision and strategy, including:

• The four key elements of a good vision statement

• Three ways to determine your mission

• The four pillars of great product management

• How writing helps you gain clarity

• How culture influences product

• Tips on how to structure a strategy session

• Advice on building team culture and improving work relationships

• What’s coming soon at YouTube

—

Brought to you by Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Wix Studio—The web creation platform built for agencies

—

Find the transcript at: https://www.lennysnewsletter.com/p/crafting-a-compelling-product-vision

—

Where to find Ebi Atawodi:

• X: https://twitter.com/ebiatawodi

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

• YouTube mixes: https://www.youtube.com/@EbiAtawodi/videos

—

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) Ebi’s background

(04:31) Four key elements of a product vision

(08:14) Examples of lofty but attainable visions

(11:43) Vision vs. mission 

(13:23) Examples of visions and missions from notable companies

(15:00) A simple framework for outlining a vision 

(20:51) Other methods for outlining a vision 

(23:29) The impact of writing clear headlines

(26:41) Using mockups to frame your vision

(28:24) A step-by-step approach to developing a vision

(32:58) Ebi’s “10 Things” document

(37:47) A quick summary of Ebi’s tips

(40:56) How to use the “10 Things” doc in a strategy session

(43:11) The three concentric circles of evangelizing 

(47:48) The cadence of developing a vision and bringing it to life

(49:26) Visions vs. micro visions

(52:58) First steps in developing a vision

(55:12) Infrastructure is the product

(56:39) Clarity and conviction, the main jobs of PMs

(59:58) Ebi’s narrative doc

(1:04:59) Conviction, its role in the job, and how to build it

(1:08:20) How to build company culture

(1:17:06) The monolithic culture at Uber

(1:19:09) The culture Ebi embeds in her teams

(1:23:58) How to evaluate your relationship with your engineering manager 

(1:26:02) What’s new at YouTube

(1:29:22) Ebi’s closing thoughts

(1:30:45) Lightning round

—

Referenced:

• Andre Albuquerque on LinkedIn: https://www.linkedin.com/in/andre-albuquerque

• TED’s mission: https://www.ted.com/about/our-organization

• Stripe’s operating principles: https://stripe.com/jobs/culture

• Microsoft’s vision and mission: https://www.microsoft.com/en-us/about

• Tesla’s mission statement: https://www.tesla.com/blog/mission-tesla

• Lyft’s mission on Comparably: https://www.comparably.com/companies/lyft/mission

• Ebi’s playbooks and templates: https://docs.google.com/presentation/d/1tU3jpbq_xHcF4x1bdANCVBsO6rbQ8h1HqvdQfwGW4MA/edit

• Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

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

• Seinfeld meme: https://seinfeldmemes.com/you-know-how-to-take-the-reservation/

• Travis Kalanick on LinkedIn: https://www.linkedin.com/in/traviskalanick/

• Wimdu: https://www.wimdu.com/

• Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer): https://www.lennyspodcast.com/leaving-big-tech-to-build-the-1-technology-newsletter-gergely-orosz-the-pragmatic-engineer/

• The 48 Laws of Power: https://www.amazon.com/48-Laws-Power-Robert-Greene/dp/0140280197

• The God of Small Things: https://www.amazon.com/God-Small-Things-Novel/dp/0812979656/

• Outliers: The Story of Success: https://www.amazon.com/Outliers-Story-Success-Malcolm-Gladwell/dp/0316017930

• All About Love: https://www.amazon.com/All-About-Love-New-Visions/dp/0060959479

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

• Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4

• Sleep Cycle: https://www.sleepcycle.com/

• Nanit: https://www.nanit.com/

• “Invictus” by William Ernest Henley: https://www.poetryfoundation.org/poems/51642/invictus

• Burning Man: https://burningman.org/

—

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.

Inbal Shani is the chief product officer at GitHub, where she leads core product management, along with product strategy, marketing, open source, and communities, including the development of GitHub Copilot. Prior to joining GitHub, she led engineering and product teams at Amazon and Microsoft. In today’s conversation, we discuss:

• What Inbal believes is overhyped and underhyped in the rapidly changing field of AI

• How AI-driven code generation is changing software development

• Her take on whether AI will replace developers

• How software development looks in 3 to 5 years

• How product teams operate at GitHub

• GitHub’s Next team, and other ways the company fosters a culture of innovation

• The success metrics and philosophy behind GitHub’s Copilot

—

Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Sanity—The most customizable content layer to power your growth engine | HelpBar by Chameleon—The free in-app universal search solution built for SaaS

—

Find the transcript at: https://www.lennyspodcast.com/the-future-of-ai-in-software-development-inbal-shani-cpo-of-github/#transcript

—

Where to find Inbal Shani:

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

—

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) Inbal’s background

(04:17) Why generative AI is not going to replace developers in the near future 

(05:54) Why AI-driven testing is underhyped

(07:48) What the next 3 to 5 years will look like

(10:13) Stats around the use of GitHub Copilot 

(12:07) How Copilot enables engineers to work more efficiently

(13:38) Common mistakes when adopting AI into your workflows

(16:42) How GitHub operationalizes “dogfooding”

(18:46) The philosophy behind Copilot

(20:24) Copilot’s success metrics

(24:54) How Copilot encourages collaboration

(26:37) What we lose when AI writes code for us

(29:35) A retrospective on the generative AI space

(30:47) Inbal’s thoughts on the future of AI

(32:35) How to make space for innovative product ideas

(34:37) How GitHub stays on the cutting edge of innovation

(36:44) The GitHub Next team

(39:20) Advice for early product managers

(42:17) Inbal’s “biggest learning” from her career

(45:34) Inbal’s closing thoughts

(46:19) Lightning round

—

Referenced:

• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennyspodcast.com/how-to-measure-and-improve-developer-productivity-nicole-forsgren-microsoft-research-github-goo/

• DORA: https://dora.dev/

• The role of AI in product development | Ryan J. Salva (VP of Product at GitHub, Copilot): https://www.lennyspodcast.com/the-role-of-ai-in-new-product-development-ryan-j-salva-vp-of-product-at-github-copilot/

• GitHub Universe 2023 day 2 keynote: The productivity platform for all developers: https://www.youtube.com/watch?v=h_o9kFPVeiw

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

• TomTom: https://www.tomtom.com/

• Failing Forward: Turning Mistakes into Stepping Stones for Success: https://www.amazon.com/Failing-Forward-Turning-Mistakes-Stepping/dp/0785288570/

• Good to Great: Why Some Companies Make the Leap and Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996

• Turning the Flywheel: A Monograph to Accompany Good to Great: https://www.amazon.com/Turning-Flywheel-Monograph-Accompany-Great/dp/0062933795

• Dare to Lead Like a Girl: How to Survive and Thrive in the Corporate Jungle: https://www.amazon.com/Dare-Lead-Like-Girl-Corporate/dp/1538163527

• All the Light We Cannot See on Netflix: https://www.netflix.com/title/81083008

• The Wheel of Time on Amazon Prime: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R

—

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 special episode of the podcast where I’ve curated my favorite interview questions that guests have shared, among over 100 podcast guests. Whether you’re a hiring manager, currently interviewing, or simply intrigued by the creative and perceptive questions that top product leaders rely on to find top talent, these questions offer unique insights into the strategies and philosophies that shape successful interviews.

—

Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps | Eppo—Run reliable, impactful experiments

—

Find the transcript at: ⁠https://www.lennysnewsletter.com/p/my-favorite-interview-questions-from

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, you’ll hear from:

(00:00) Lenny

(03:21) Eeke De Miliano

(03:57) Geoff Charles

(04:31) Shishir Mehrotra

(08:44) Yuhki Yamashita

(09:56) Katie Dill

(10:36) Karri Saarinen

(11:02) Camille Hearst

(11:28) Jiaona Zhang

(12:43) Noah Weiss

(13:10) Ben Williams

(14:41) Meltem Kuran Berkowitz

(15:29) Paige Costello

(16:13) Nikhyl Singhal

(17:51) Ayo Omojola

(18:20) Scott Belsky

(19:17) Lauryn Isford

(19:46) Paul 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.

Tom Conrad is the CEO of Zero and on the board of Sonos. He began his career in engineering at Apple, where he helped build key features that remain in iOS today. Tom was previously the VP of Product at Snap and the chief technology officer of Pandora. He also held leadership positions at notable tech flops Pets.com and Quibi, giving him a unique perspective not only on what it takes to build a successful company but also on lessons from failure. In today’s conversation, we discuss:

• Lessons learned from the infamous failures of Pets.com and Quibi

• Lessons learned from the successes of Apple, Pandora, and Snap

• Advice on choosing where to work

• Understanding the math formula of a business

• How to avoid burnout

• Why Tom says not everyone needs to be a founder

• What he’s building now

—

Brought to you by Coda—Meet the evolution of docs | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | HelpBar by Chameleon—the free in-app universal search solution built for SaaS

—

Find the transcript at: https://www.lennysnewsletter.com/p/billion-dollar-failures-and-billion

—

Where to find Tom Conrad:

• X: https://twitter.com/tconrad

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

—

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) Tom’s background

(04:40) Landing a gig at Apple

(07:41) Pioneering the blinking folder design on iOS

(11:04) Advice on choosing where to work

(12:43) The importance of trusting your gut when it comes to people

(14:05) Lessons from failed ventures

(17:32) Why and how Pets.com shut down 

(18:30) How Tom’s experience at Quibi renewed his passion for building

(28:48) Takeaways from Quibi and why it ultimately failed

(31:42) Failing is okay

(35:04) Tom’s career at Apple

(39:11) Lessons from You Don’t Know Jack

(40:24) Lessons from building Pandora

(48:24) Looking back at Pandora and what could have been done differently

(55:17) How Tom became VP of Product at Snapchat

(1:01:31) Tom’s philosophy on being involved as CEO

(1:05:51) Tom’s current role as CEO of Zero, and what he’s learned along the way

(1:10:37) How Zero builds product

(1:18:33) Advice on work-life balance 

(1:27:22) Contrarian corner: why not everyone needs to be a founder

(1:30:08) Lightning round

—

Referenced:

• Ron Lichty on LinkedIn: https://www.linkedin.com/in/ronlichty/

• What happened to Pets.com?: https://fourweekmba.com/pets-com-failure/

• 11 reasons why Quibi crashed and burned in less than a year: https://www.theverge.com/2020/10/22/21528404/quibi-shut-down-cost-subscribers-content-tv-movies-katzenberg-whitman-tiktok-netflix

• Meg Whitman: https://en.wikipedia.org/wiki/Meg_Whitman

• Jeffrey Katzenberg on LinkedIn: https://www.linkedin.com/in/jeffrey-katzenberg-4b3b47123/

• John Sculley on LinkedIn: https://www.linkedin.com/in/johnsculley/

• Flickr: https://www.flickr.com/

• How Pandora Soothed the Savage Beast: https://www.fastcompany.com/3001052/how-pandora-soothed-savage-beast

• Joe Kennedy on LinkedIn: https://www.linkedin.com/in/joe-kennedy-329417/

• Why Did Yahoo Pay $160 Million for Musicmatch?: https://www.wired.com/2007/07/why-did-yahoo-p/

• TikTok Is the New TV: https://www.wired.com/story/tiktok-new-show-tv-takeover/

• Evan Spiegel on X: https://twitter.com/evanspiegel

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• What sets great teams apart | Lane Shackleton (CPO of Coda): https://www.lennyspodcast.com/what-sets-great-teams-apart-lane-shackleton-cpo-of-coda/

• Flashtags: https://lane.substack.com/p/flashtags

• Patrick Spence on LinkedIn: https://www.linkedin.com/in/patrickspence/

• The Philosophy of Ikigai: 3 Examples About Finding Purpose: https://positivepsychology.com/ikigai

• The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life: https://www.amazon.com/Subtle-Art-Not-Giving-Counterintuitive/dp/0062457713

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Hyperion: https://www.amazon.com/Hyperion-Cantos-Dan-Simmons/dp/0553283685

• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285/

• Mrs. Davis on Peacock: https://www.peacocktv.com/stream-tv/mrs-davis

• Watchmen on HBO: https://www.hbo.com/watchmen

• Lost on Hulu: https://www.hulu.com/series/lost-466b3994-b574-44f1-88bc-63707507a6cb

• Eartune replacement tips: https://eartune.com/products/eartune-fidelity-ufa

• Charles Eames’s quote: https://www.brainyquote.com/quotes/charles_eames_169188

• Compuserve: https://www.compuserve.com/

• Steve Wilhite: https://en.wikipedia.org/wiki/Steve_Wilhite

—

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.

Paul Millerd spent several years working in strategy consulting and on the “default path” before deciding to walk away to work on his own in 2017. His book, The Pathless Path, chronicles his own journey and deep dive into the history of work and has been read by more than 40,000 people. His podcast, The Pathless Path Podcast, highlights conversations with others following unconventional paths. He also runs the online training business StrategyU, helping people learn the skills of consulting without having to work in the industry. In our conversation, Paul shares:

• An explanation of the “default path” and the “pathless path”

• Signs you may be stuck on the default path

• How to inch your way toward the pathless path

• Why Paul suggests everyone should take a three-month sabbatical

• Tips for embracing fear and betting on yourself

• How to work through the fear of losing money and prestige

—

Brought to you by Sanity—The most customizable content layer to power your growth engine | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door | Wix Studio—The web creation platform built for agencies

—

Find the full transcript at: https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/

—

Where to find Paul Millerd:

• X: https://twitter.com/p_millerd

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

• Website: https://pathlesspath.com/

• Newsletter: https://newsletter.pathlesspath.com

• YouTube: https://www.youtube.com/channel/UCofS_FvauuHc-x6mq7yz6nA

• Podcast: https://think-boundless.com/podcast/

• Email: paul@strategyu.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) Paul’s background

(04:33) An explanation of the “default path”

(06:32) Questions to help clarify which path you are on

(07:35) Paul’s thoughts on “remixing your path”

(09:57) An explanation of the “pathless path” 

(12:06) Examples of the pathless path

(13:54) Why meaning is hard to find and sustain on a traditional career path 

(16:05) A case for the three-month sabbatical 

(18:16) A mindfulness and self-reflection exercise

(20:18) Why Paul recommends three months

(22:28) Advice to founders on offering sabbaticals

(23:40) Other tactics for self-discovery

(27:08) The variability of income in self-employed roles 

(29:12) Methods for staying afloat after leaving your job

(30:42) Tips for reframing your thoughts around money

(33:19) Why betting on yourself usually works out

(34:46) The importance of setting aside time for creative pursuits

(36:22) How to dip your toes in and find your path 

(37:53) Lenny’s personal journey

(39:27) Advice on dealing with the naysayers 

(40:22) How to acknowledge and tame your fears

(44:52) The “ship, quit, and learn” framework

(46:39) Why the pathless path is one of constant reinvention

(51:27) Paul’s response to criticism 

(58:02) First steps for getting started on your journey

(55:42) Lightning round

—

Referenced:

• The Pathless Path: Imagining a New Story for Work and Life: https://www.amazon.com/Pathless-Path-Imagining-Story-Work/dp/B09QF6Q421

• David Autor on X: https://twitter.com/davidautor

• Tim Ferriss’s blog: https://tim.blog/

• Why you should define your fears instead of your goals | Tim Ferriss: https://www.youtube.com/watch?v=5J6jAC6XxAI

• How Lenny Rachitsky Got 531,000 Substack Subscribers: https://www.youtube.com/watch?v=DMZem1NYfpM

• The Lindy effect: https://en.wikipedia.org/wiki/Lindy_effect

• StrategyU: https://strategyu.co/

• David Deming’s website: https://www.daviddeming.com/nyt-columns

• The Great Work of Your Life: A Guide for the Journey to Your True Calling: https://www.amazon.com/Great-Work-Your-Life-Journey/dp/0553386077

• Wanting: The Power of Mimetic Desire in Everyday Life: https://www.amazon.com/Wanting-Power-Mimetic-Desire-Everyday/dp/1250262488

• Roadrunner: A Film About Anthony Bourdain: https://www.hbo.com/movies/roadrunner-a-film-about-anthony-bourdain

• Nuna travel stroller: https://nunababy.com/usa/trvl-easy-fold-compact-stroller

• Build Your Own Chatbot with OpenAI GPT-3 and Streamlit: https://medium.com/@avra42/build-your-own-chatbot-with-openai-gpt-3-and-streamlit-6f1330876846

—

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.

Melissa Perri is the CEO of Produx Labs, a product management training organization; author of the seminal PM book The Build Trap; and a former Harvard Business School professor of product management. Denise Tilles is the CPO at Grocket, Melissa’s colleague at Produx Labs, and a seasoned product leader with over a decade of experience. Together they authored the new book Product Operations: How successful companies build better products at scale. In today’s episode, they share insights, strategies, and real-world experiences to master all things product ops. We discuss:

• What exactly product operations is

• The three pillars of the product ops role

• The biggest benefits of adding product ops to your organization

• Which tasks product managers should offload to product ops and which they need to own

• How to help PMs embrace the value of product ops

• Examples of companies that have implemented product ops well

• Who and how to hire for this role

—

This entire episode is brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams

—

Find the full transcript at: https://www.lennyspodcast.com/the-ultimate-guide-to-product-operations-melissa-perri-and-denise-tilles/#transcript

—

Where to find Melissa Perri:

• X: https://twitter.com/lissijean

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

• Website: https://produxlabs.com/

—

Where to find Denise Tilles:

• X: https://twitter.com/dtilles

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

• Website: https://www.denisetilles.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 our guests, Melissa Perri and Denise Tilles

(03:46) How common is the product operations role?

(07:41) The benefits of having a product ops person in your organization

(09:16) How to help PMs embrace the value of product ops

(11:44) The three pillars of the product ops role

(15:25) How user research fits in

(18:35) Why product ops will be an essential role for product managers to thrive

(24:24) Which tasks product managers should offload to product ops and which they need to own

(28:58) Project management vs. product ops

(29:44) The jobs of a product ops person

(37:38) Why the product ops role will never become obsolete

(39:31) How many product ops people you need

(45:13) First steps in building out a product ops team

(47:06) What to look for in your first hire

(51:11) Key skills needed for a product ops person

(57:29) Who product ops should report to

(59:50) An example of rolling out product ops at Athena Health

(1:09:35) Lightning round

—

Referenced:

• Product Operations: How successful companies build better products at scale: https://www.productoperations.com/

• Produx Labs: https://produxlabs.com

• How to create a winning product strategy | Melissa Perri: https://www.lennyspodcast.com/how-to-create-a-winning-product-strategy-melissa-perri/

• Blake Samic on LinkedIn: https://www.linkedin.com/in/blakesamic/

• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/149197379X

• Athena Health: https://www.athenahealth.com/

• Pendo: https://www.pendo.io/

• PopSQL: https://popsql.com/

• Understanding the role of product ops | Christine Itwaru (Pendo): https://www.lennyspodcast.com/understanding-the-role-of-product-ops-christine-itwaru-pendo/

• Doodle: https://doodle.com/en/

• Stephanie Leue on LinkedIn: https://www.linkedin.com/in/stephanie-leue/

• Jira: https://www.atlassian.com/software/jira

• Dovetail: https://dovetail.com/

• Looker: https://cloud.google.com/looker/

• Brian Bhuta on LinkedIn: https://www.linkedin.com/in/brianbhuta/

• 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/

• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennyspodcast.com/thinking-beyond-frameworks-casey-winters-pinterest-eventbrite-airbnb-tinder-canva-reddit-grubhub/

• Shared services model: https://www.gartner.com/en/finance/insights/shared-services-model

• Shintaro Matsui on LinkedIn: https://www.linkedin.com/in/smatsui/

• Tableau: https://www.tableau.com/

• Jen Cardello on LinkedIn: https://www.linkedin.com/in/jencardello/

• Tim Davenport on LinkedIn: https://www.linkedin.com/in/tim-davenport-28249b9/

• Traffic: Genius, Rivalry, and Delusion in the Billion-Dollar Race to Go Viral: https://www.amazon.com/Traffic-Genius-Rivalry-Delusion-Billion-Dollar/dp/0593299752

• The Art of Action: https://www.amazon.com/Art-Action-10th-Anniversary/dp/1529376963

• Continuous Discovery Habits: Discover Products that Create Customer Value and Business Value: https://www.amazon.com/Continuous-Discovery-Habits-Discover-Products/dp/1736633309

• Deutschland89 on Hulu: https://www.hulu.com/series/deutschland-89-a4cf05f7-b4f2-44c7-84a1-4034671944b9

• The Fall of the House of Usher on Netflix: https://www.netflix.com/title/81414665

• Love Is Blind on Netflix: https://www.netflix.com/title/80996601

• The Haunting of Hill House on Netflix: https://www.netflix.com/title/80189221

• Dragonboat: https://dragonboat.io/solution/product-operations/

• Vistaly: https://www.vistaly.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.

Brian Chesky is the co-founder and CEO of Airbnb. Under Brian’s leadership, Airbnb has grown into a community of over 4 million hosts who have welcomed more than 1.5 billion guests across over 220 countries and regions. I had the privilege of working under his leadership, so it is a great honor to have him on the show. We discuss:

• How Airbnb has shifted their thinking on product management

• Why bureaucracy happens in companies, and how to avoid it

• The importance of founders diving into the details

• Why Airbnb moved away from traditional growth channels and what they are doing instead

• Airbnb’s newly released features

• How and why Brian encourages his team to set ambitious goals

• Why he says he still has a lot to prove

—

Brought to you by Sidebar—Catalyze your career with a Personal Board of Directors | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Eppo—Run reliable, impactful experiments

—

Find the full transcript at: https://www.lennyspodcast.com/brian-cheskys-new-playbook/#transcript

—

Where to find Brian Chesky:

• X: https://twitter.com/bchesky

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

—

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

(05:18) The current structure of product management at Airbnb

(09:21) How fast-moving companies become slow-moving bureaucracies

(12:20) Brian’s thoughts on performance marketing

(13:50) Airbnb’s rolling two-year roadmap

(15:30) Brian’s journey as CEO in a growing company

(18:34) Best practices for A/B testing 

(20:30) Who inspired Airbnb’s new direction

(23:18) The first changes Brian implemented at the onset of the pandemic

(24:51) Why founders should be “in the details” 

(30:15) Airbnb’s marketing, communication, and creative functions

(31:38) Advice for founders on how to lead

(34:15) Tips for implementing Airbnb’s business methodology 

(38:48) Airbnb’s winter release

(41:47) Why Airbnb no longer has separate guest and host teams 

(42:38) Brian’s thoughts on design trends 

(45:36) The importance of empowering hosts with great tools

(45:57) How setting ambitious goals improves team performance 

(50:05) Tips for preventing burnout

(56:02) Tips for personal and professional growth 

(58:19) Why Brian says he still has a lot to prove

(1:02:58) Paying it forward

(1:05:03) A fun fact about Brian

(1:09:26) Airbnb’s origin story

—

Referenced:

• Localmind: https://www.crunchbase.com/organization/localmind

• Config 2023 in review: https://www.figma.com/blog/config-2023-recap/

• Why Founders Fail: The Product CEO Paradox: https://techcrunch.com/2013/08/10/why-founders-fail-the-product-ceo-paradox/

• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/

• Jony Ive on Crunchbase: https://www.crunchbase.com/person/jonathan-ive

• Charles Eames: https://en.wikipedia.org/wiki/Charles_Eames

• Airbnb 2023 Winter Release: https://news.airbnb.com/en-in/airbnb-2023-winter-release-introducing-guest-favorites-a-collection-of-the-2-million-most-loved-homes-on-airbnb/

• Airbnb 2023 winter release reel: https://x.com/bchesky/status/1722243847751970861?s=20

• John Wooden’s website: https://coachwooden.com/

• An 85-year Harvard study found the No. 1 thing that makes us happy in life: It helps us ‘live longer’: https://www.cnbc.com/2023/02/10/85-year-harvard-study-found-the-secret-to-a-long-happy-and-successful-life.html

• Sam Altman on X: https://twitter.com/sama

• Alfred P. Sloan: https://en.wikipedia.org/wiki/Alfred_P._Sloan

• Bob Dylan quote: https://quotefancy.com/quote/950807/Bob-Dylan-An-artist-has-got-to-be-careful-never-really-to-arrive-at-a-place-where-he

• OpenAI: https://openai.com/

• Michael Seibel’s website: https://www.michaelseibel.com/

• Y Combinator: https://www.ycombinator.com/

• The Norman Rockwell Museum: https://www.nrm.org/

• Rhode Island School of Design: https://www.risd.edu/

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Nathan Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

—

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.

Ramesh Johari is a professor at Stanford University focusing on data science methods and practice, as well as the design and operation of online markets and platforms. Beyond academia, Ramesh has advised some incredible startups, including Airbnb, Uber, Bumble, and Stitch Fix. Today we discuss:

• What exactly a marketplace is, if you boil it down

• What you need to get right to build a successful marketplace

• How to optimize any marketplace

• An easy litmus test to see if there’s an opportunity to build a marketplace in the space

• The role of data science in successful marketplaces

• Ramesh’s philosophy on experimentation and AI

• Advice on implementing rating systems

• Why learning isn’t free

—

Brought to you by Sanity—The most customizable content layer to power your growth engine | Hex—Helping teams ask and answer data questions by working together | Eppo—Run reliable, impactful experiments

—

Find the full transcript at: https://www.lennyspodcast.com/marketplace-lessons-from-uber-airbnb-bumble-and-more-ramesh-johari-stanford-professor-startup/

—

Where to find Ramesh Johari:

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

• Website: https://web.stanford.edu/~rjohari/

• X: https://twitter.com/rameshjohari

—

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) Ramesh’s background

(04:31) A brief overview of what a marketplace is

(08:10) The role of data science in marketplaces

(11:21) Common flaws of marketplaces

(16:43) Why every founder is a marketplace founder

(20:26) How Substack increased value to creators by driving demand

(20:58) An example of overcommitting at eBay

(22:24) An easy litmus test for marketplaces 

(25:52) Thoughts on employees vs. contractors

(28:02) How to leverage data scientists to improve your marketplace

(34:10) Correlation vs. causation

(35:27) Decisions that should be made using data

(39:29) Ramesh’s philosophy on experimentation

(41:06) How to find a balance between running experiments and finding new opportunities

(44:11) Badging in marketplaces

(46:04) The “superhost” badge at Airbnb

(49:59) How marketplaces are like a game of Whac-A-Mole

(52:41) How to shift an organization’s focus from impact to learning

(55:43) Frequentist vs. Bayesian A/B testing 

(57:50) The idea that learning is costly

(1:01:55) The basics of rating systems

(1:04:41) The problem with averaging

(1:07:14) Double-blind reviews at Airbnb

(1:08:55) How large language models are affecting data science

(1:11:27) Lightning round

—

Referenced:

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

• Upwork (formerly Odesk): https://www.upwork.com/

• Ancient Agora: https://en.wikipedia.org/wiki/Ancient_Agora_of_Athens

• Trajan’s Market: https://en.wikipedia.org/wiki/Trajan%27s_Market

• Kayak: https://www.kayak.com/

• UrbanSitter: https://www.urbansitter.com/

• Thumbtack: https://www.thumbtack.com/

• Substack: https://substack.com/

• Ebay: https://www.ebay.com/

• Coase: “The Nature of the Firm”: https://en.wikipedia.org/wiki/The_Nature_of_the_Firm

• Stitch Fix: https://www.stitchfix.com/

• A/B Testing with Fat Tails: https://www.journals.uchicago.edu/doi/abs/10.1086/710607

• The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon): https://www.lennyspodcast.com/the-ultimate-guide-to-ab-testing-ronny-kohavi-airbnb-microsoft-amazon/

• Servaes Tholen on LinkedIn: https://www.linkedin.com/in/servaestholen/

• Bayesian A/B Testing: A More Calculated Approach to an A/B Test: https://blog.hubspot.com/marketing/bayesian-ab-testing

• Designing Informative Rating Systems: Evidence from an Online Labor Market: https://arxiv.org/abs/1810.13028

• Reputation and Feedback Systems in Online Platform Markets: https://faculty.haas.berkeley.edu/stadelis/Annual_Review_Tadelis.pdf

• How to Lie with Statistics: https://www.amazon.com/How-Lie-Statistics-Darrell-Huff/dp/0393310728

• David Freedman’s books on Amazon: https://www.amazon.com/stores/David-Freedman/author/B001IGLSGA

• Four Thousand Weeks: Time Management for Mortals: https://www.amazon.com/Four-Thousand-Weeks-Management-Mortals/dp/0374159122

• The Alpinist on Prime Video: https://www.amazon.com/Alpinist-Peter-Mortimer/dp/B09KYDWVVC

• Only Murders in the Building on Hulu: https://www.hulu.com/series/only-murders-in-the-building-ef31c7e1-cd0f-4e07-848d-1cbfedb50ddf

—

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.

Maggie Crowley is VP of product at Toast and previously vice president and head of product at Charlie Health, senior director of product management at Drift, and a PM at TripAdvisor. She’s also the host of Build, a podcast dedicated to product and product management. In today’s conversation, Maggie shares:

• The value of building a broad-based PM skill set

• Three qualities of the best product managers

• A step-by-step guide for crafting a product strategy

• How to break into PM

• Why great writing is often just simplifying your writing

• Why being too data-driven is a red flag

• The impact of content creation on Maggie’s career

—

Brought to you by Productroadmap.ai—AI to connect your roadmaps to revenue | Composer—the AI-powered trading platform | Eppo—Run reliable, impactful experiments

—

Find the full transcript at: https://www.lennyspodcast.com/mastering-product-strategy-and-growing-as-a-pm-maggie-crowley-toast-drift-tripadvisor/

—

Where to find Maggie Crowley:

• X: https://twitter.com/maggiecrowley

• LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/

—

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) Maggie’s background

(04:06) Three common traits among the best product managers

(09:33) Strategy is an important but small part of the job

(11:14) How to get better at simplification

(13:39) Tips on simplifying your writing

(15:13) Ownership as a PM

(17:53) Examples of simplifying your work

(19:39) Maggie’s Slack support group

(21:37) How to improve on following up on your work

(23:23) A realistic time horizon for PMs

(26:31) Staying in your role vs. trying a new opportunity

(27:37) The importance of “carrying the water” 

(28:56) Pros and cons of the PM job

(31:42) Advice on landing a PM role

(34:36) Maggie’s step-by-step process for writing your product strategy

(39:55) Not every feature needs a strategy

(46:29) The value of working through the process

(48:09) Maggie’s one-pager doc 

(54:16) Contrarian corner

(55:44) The worst product Maggie ever shipped

(58:33) Why being “data-driven” is a red flag

(1:01:10) Content creation as a career accelerator

(1:14:27) Closing thoughts

(1:15:17) Lightning round

—

Referenced:

• David Cancel on LinkedIn: https://www.linkedin.com/in/dcancel/

• On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548

• Notion: https://www.notion.so/

• The Minto Pyramid Principle and the SCR Framework: https://www.lennysnewsletter.com/p/minto-pyramid-principle-scr

• Drift: https://www.drift.com/

• Maggies Top 5 Product Lessons for 2021: https://www.drift.com/podcasts/build/?wchannelid=hg0p3zf4yx&wmediaid=nxrdvmotr3

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/

• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennyspodcast.com/inside-linear-building-with-taste-craft-and-focus-karri-saarinen-co-founder-designer-ceo/

• Adam Medros on LinkedIn: https://www.linkedin.com/in/amedros/

• How Figma builds product: https://www.lennysnewsletter.com/p/how-figma-builds-product

• Strategy Document Template: https://docs.google.com/document/d/1frggEj_gfFD4--8eNkkyY-zHryXbN5uIS8uiMDCYVes/edit

• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennyspodcast.com/shreyas-doshi-on-pre-mortems-the-lno-framework-the-three-levels-of-product-work-why-most-execution-problems-are-strategy-problems-and-roi-vs-opportunity-cost-thinking/

• Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_122232

• The Presentation Secrets of Steve Jobs: How to Be Insanely Great in Front of Any Audience: https://www.amazon.com/Presentation-Secrets-Steve-Jobs-Insanely/dp/0071636080

• Thinking in Bets: Making Smarter Decisions When You Dont Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216371

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212/r

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Future: https://www.future.co/

• Ladder: https://www.joinladder.com/

• Pump Log: https://pumplogapp.com/

• Huckleberry: https://huckleberrycare.com/

• Toast: https://pos.toasttab.com/

• Careers at Toast: https://careers.toasttab.com/homepage

• What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennyspodcast.com/what-differentiates-the-highest-performing-product-teams-john-cutler-amplitude-the-beautiful-mess/

—

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.

Bill Carr is the co-author of Working Backwards: Insights, Stories, and Secrets from Inside Amazon. With a background at Amazon of over 15 years, Bill played a pivotal role in shaping the company’s global digital music and video ventures, including Amazon Music, Prime Video, and Amazon Studios. After Amazon, Bill was an Executive in Residence with Maveron, an early-stage, consumer-only venture capital firm. He later served as the chief operating officer of OfferUp, the largest mobile marketplace for local buyers and sellers in the U.S. Today he’s the co-founder of Working Backwards LLC, where he helps companies implement Amazon’s time-tested management strategies. In this episode, we discuss:

• What exactly “working backwards” is, and how you do it

• Why having “single-threaded leaders” is so effective

• Inside Amazon’s intense product review process

• How to actually follow the “disagree and commit” principle

• The thinking behind the principle “Leaders are right, a lot”

• Input vs. output metrics

• Fostering a culture of risk-taking and innovation

• The role and responsibilities of a “bar raiser” in your hiring, and how it significantly improves the success rate of new hires

—

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—

Find the full transcript at: https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/

—

Where to find Bill Carr:

• X: https://twitter.com/BillCarr89

• LinkedIn: https://www.linkedin.com/in/bill-carr/

• Website: https://www.workingbackwards.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) Bill’s background

(04:26) Amazon’s workplace evolution

(09:54) Amazon’s “fitness function”

(11:44) Single-threaded leadership

(18:07) Implementing a program orientation with single-threaded leadership

(20:16) The GM model vs. single-threaded leadership

(21:31) Functional countermeasures needed for single-threaded leadership

(25:22) Embracing the “disagree and commit” principle

(30:22) Understanding disagreements

(32:41) Deciphering Amazon’s “Leaders are right, a lot” principle

(35:25) An explanation of the working backwards framework

(41:16) PR FAQ process: Amazon’s innovation engine

(44:47) Deconstructing the PR FAQ structure

(43:49) The concentric circle model for sharing PR FAQs

(44:55) The customer problem-solution statement

(47:52) Create a product funnel, not a product tunnel

(51:19) How Amazon promotes action vs. talk

(54:35) Amazon’s flywheel and input metrics

(1:00:51) Signs you’ve got a good input metric

(1:04:23) How mistakes can still be made with working backwards

(1:06:54) Why disagreements aren’t necessarily signs products will fail

(1:08:02) Examples of failed Amazon projects

(1:09:55) Cultivating risk-taking and accepting failure

(1:13:57) Amazon’s “bar-raiser” practice for hiring

(1:18:21) Selecting Amazon’s bar raisers

(1:20:41) Advice on implementing practices from Working Backwards

(1:23:10) Bill’s work as an advisor

(1:26:05) Lightning round

—

Referenced:

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• Jeff Bezos on X: https://twitter.com/jeffbezos

• D.E. Shaw: https://www.deshaw.com/

• Eric Ries’s website: https://theleanstartup.com/

• GM business model: https://fourweekmba.com/general-motors-business-model/

• Rick Dalzell on LinkedIn: https://www.linkedin.com/in/richarddalzell/

• The Effective Decision by Peter F. Drucker: https://hbr.org/1967/01/the-effective-decision

• Template: Working Backwards PR FAQ: https://www.workingbackwards.com/resources/working-backwards-pr-faq

• Good to Great: Why Some Companies Make the Leap and Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996

• The Amazon flywheel: https://feedvisor.com/resources/amazon-trends/amazon-flywheel-explained/

• Sixsigma: https://www.6sigma.us/

• Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries: https://www.amazon.com/Loonshots-Nurture-Diseases-Transform-Industries/dp/1250185963

• Andy Jassy on LinkedIn: https://www.linkedin.com/in/andy-jassy-8b1615/

• Implementing Amazon’s Bar Raiser Process in Hiring: A Quick Guide: https://www.barraiser.com/blogs/implementing-amazons-bar-raiser-process-in-hiring

• Microspeak: The As-Appropriate (AA) interviewer: https://devblogs.microsoft.com/oldnewthing/20231017-00/?p=108897

• The Practice of Management: https://www.amazon.com/Practice-Management-Peter-F-Drucker/dp/0060878975

• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459

• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537

• Seveneves: https://www.amazon.com/Seveneves-Neal-Stephenson/dp/0062334514

• A Gentleman in Moscow: https://www.amazon.com/A-Gentleman-in-Moscow/dp/0143110438

• Dune on Prime Video: https://www.amazon.com/Dune-Timoth%C3%A9e-Chalamet/dp/B09LJXY4PH

• A Spy Among Friends: https://www.imdb.com/title/tt15565872/

• Zipp 303 Firecrest tubeless disc brake: https://www.sram.com/en/zipp/models/wh-303-ftld-a1

• The Fifth Discipline: The Art & Practice of the Learning Organization: https://www.amazon.com/Fifth-Discipline-Practice-Learning-Organization/dp/0385517254

—

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.

Eric Ries is the creator of the Lean Startup methodology, author of the New York Times bestseller The Lean Startup, and founder of the Long-Term Stock Exchange (LTSE). He’s also a multi-time founder and currently advises startups, VC firms, and larger companies on business and product strategy. In today’s episode, we discuss:

• The current state of the Lean Startup methodology

• Common misconceptions about the Lean Startup methodology

• Understanding how to actually think about MVPs (minimum viable products)

• When to pivot and when to stay the course

• Thoughts on AI and how to deal with uncertainty

• How to structure your company around core values and create products that benefit humanity

• The philosophy behind Eric’s current big idea: the Long-Term Stock Exchange

• Much more

—

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—

Find the full transcript at: https://www.lennyspodcast.com/reflections-on-a-movement-eric-ries-creator-of-the-lean-startup-methodology/#transcript

—

Where to find Eric Ries:

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

• X: https://twitter.com/ericries

• Website: https://theleanstartup.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) Eric’s background

(04:46) Eric’s recent activities and projects

(06:23) Eric’s start in advising and first-principles thinking

(10:56) Lessons from designing the Lean Startup process

(14:04) The current state of lean startup methodology

(22:33) Common misconceptions about the methodology

(24:28) Changes Eric would make in an updated version of Lean Startup

(27:52) An explanation of minimum viable product (MVP) and why Eric still stands by the process

(37:36) An example of “Less is more”

(41:24) More on MVPs and the importance of testing your hypotheses 

(41:24) How LTSE had to pivot after a partnership fell apart

(48:37) Eric’s take on the concept of craft

(53:36) Why getting fired for standing by your conviction can be a career accelerator

(55:17) Tech’s mental health crisis

(56:28) Advice for founders stuck in a “zombie company”

(1:00:16) How continuous pivots shape a company’s vision, with a real-life story

(1:08:20) Challenges in assessing companies from an external perspective

(1:13:17) Practical advice for businesses considering a pivot

(1:18:42) The impact of artificial intelligence

(1:26:59) The current capabilities of ChatGPT and its potential use as an equalizer in the marketplace

(1:31:26) Eric’s current work with founders on human flourishing

(1:42:40) Advice for founders who want to build ethical companies 

(1:49:37) Examples of first-principles thinking

(1:53:42) Why shareholder primacy theory is wrong

(1:55:19) The “spiritual holding company” 

(1:58:12) Lightning round

—

Referenced:

• The Long-Term Stock Exchange: https://ltse.com/

• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898

• Lean manufacturing: https://www.techtarget.com/searcherp/definition/lean-production

• Six Sigma: https://www.6sigma.us/six-sigma.php

• Clay Christensen: https://claytonchristensen.com/

• Eric Ries on 4 Common Misconceptions About Lean Startup: https://www.entrepreneur.com/starting-a-business/eric-ries-on-4-common-misconceptions-about-lean-startup/286701

• Anakin Skywalker meme: https://knowyourmeme.com/memes/for-the-better-right

• Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennyspodcast.com/inside-linear-building-with-taste-craft-and-focus-karri-saarinen-co-founder-designer-ceo/

• Snow Crash: https://www.amazon.com/Snow-Crash-Neal-Stephenson/dp/0553380958

• IMVU: https://about.imvu.com/

• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/

• Wonder Boy: Tony Hsieh, Zappos, and the Myth of Happiness in Silicon Valley: amazon.com/Wonder-Boy-Zappos-Happiness-Silicon/dp/1250829097

• Understanding Steve Jobs’s Reality Distortion Field: https://www.emexmag.com/understanding-steve-jobs-reality-distortion-field

• Paul Graham’s website:http://www.paulgraham.com/raham

• Segment: https://segment.com/

• Loom: https://www.loom.com/

• The Slack story: https://www.paperflite.com/blogs/slack-story

• The Social Network on Netflix: https://www.netflix.com/ca/title/70132721

• Thomas Kuhn: Paradigm Shift: https://www.simplypsychology.org/kuhn-paradigm.html

• Conway’s Law: the little-known principle that influences your work more than you think: https://www.atlassian.com/blog/teamwork/what-is-conways-law-acmi

• Monty Python and the Holy Grail Guards Scene on YouTube: https://www.youtube.com/watch?v=eVWH01E2weA

• Toyota Production System: https://global.toyota/en/company/vision-and-philosophy/production-system/

• Warren Buffett’s Forbes bio: https://www.forbes.com/profile/warren-buffett

• The Enlightened Capitalists: Cautionary Tales of Business Pioneers Who Tried to Do Well by Doing Good: amazon.com/Enlightened-Capitalists-Cautionary-Business-Pioneers/dp/0062880241

• The Grace of Kings (The Dandelion Dynasty): https://www.amazon.com/Grace-Kings-Dandelion-Dynasty/dp/148142428

• All Systems Red: The Murderbot Diaries: https://www.amazon.com/All-Systems-Red-Murderbot-Diaries/dp/0765397536

• Star Wars: Andor on Disney+: https://www.disneyplus.com/series/star-wars-andor/3xsQKWG00GL5

• Tesla Powerwall: https://www.tesla.com/powerwall

• Levoit Classic 300S ultrasonic smart humidifier: https://www.amazon.com/LEVOIT-Humidifiers-Ultrasonic-Essential-Customized/dp/B09C24TYGQ

• The Law of Sustainable Growth: https://www.linkedin.com/pulse/20121015181612-2157554-the-law-of-sustainable-growth/

—

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.

Paul Adams is the longtime chief product officer at Intercom, where he leads the product management, product design, data science, and research teams. Before Intercom, Paul was the global head of brand design at Facebook, a senior user researcher at Google, and a product designer at Dyson. He’s also a best-selling author, a podcast host, and a public speaker. In today’s episode, we discuss:

• Practical advice on integrating AI into your organization

• Tips and tools for learning AI as a PM

• Hilarious stories from Google and Facebook

• How to build conviction with skeptical coworkers

• Lessons learned from pricing at Intercom

• How Intercom implemented JTBD

—

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