Invest Like the Best with Patrick O'Shaughnessy

Today’s conversation is one of my all-time favorites, with someone I’ve come to respect deeply in the field of investing. My guest is Carl Kawaja, who has served as a portfolio manager at Capital Group for decades. Capital Group is among the most respected shareholders in the world, with over $2T of assets, and listening to Carl, you’ll hear why.

In our conversation, we cover Carl’s criteria for building conviction around long-term holdings, why he views uncertainty and ambiguity as healthy, and why tolerating failure is key to great investing career. Throughout our discussion, Carl connects his lessons through a variety of direct experiences, personal analogies, and broader frameworks. I love his ability to talk in the weeds about his investments in Vale and TSMC and then quickly shift to his broader thematic views like “The Empire Strikes Back.” I hope you enjoy this great conversation with Carl Kawaja.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick".

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:38] - [First question] - The two companies he has owned the longest and what they’ve taught him as an investor 

[00:16:37] - Discussing his investment style through the lens of simplicity  

[00:24:35] - A time where he worked to try and create a simplified equation but couldn’t 

[00:30:59] - Discussing his investment style through the lens of echolocation and ambiguity 

[00:36:03] - Thoughts on whether buying well or holding well is more difficult

[00:40:40] - Capital Group’s history and his river-rafting analogy in regards to the company

[00:47:48] - What he means by “The Empire Strikes Back” and relevant market themes

[00:54:50] - A brief summary of “The Empire Strikes Back”

[00:58:42] - Common reasons that he may have gotten something really wrong 

[01:03:34] - Impressions made on him by the poet Rilke

[01:09:00] - The work of Brunello Cucinelli and the nature of quality 

[01:13:08] - Advice for new investors who want to step into the field and set themselves up for success

[01:13:54] - The Visual Display of Quantitative Information 

[01:17:39] - What he’s learned about kindness

[01:19:54] - The kindest thing that anyone has ever done for him

My guest today is Stewart Butterfield, founder and CEO of Slack. Stewart’s 2014 essay “Why We Don’t Sell Saddles Here” had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models and behavior when introducing innovative products. I hope you enjoy my conversation with Stewart.

Before we transition to the episode, I also wanted to highlight our newest series Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. For more information go to joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:51] - [First question] - Discussing his essay We Don’t Sell Saddles Here  

[00:06:19] - Important contrast between innovation and the product

[00:06:46] - Who Do You Want Your Customers to Become? 

[00:08:07] - His thoughts on marketing from both ends and how he’s gotten better at it

[00:10:45] - What across Slack’s history has been the most successful market messaging creation strategy

[00:13:43] - The 5K contest and how it taught him about the design unlock of limitations

[00:17:44] - How limitations and constraints can power and incentivize innovation 

[00:21:21] - Why both of his attempts to build videogames ended up as consumer software

[00:27:55] - Whether or not there is still white space in digital communication software

[00:30:15] - The dynamic between effective communication and building communication tools

[00:34:02] - A future of digital-first companies and what that might look like

[00:40:15] - Leadership and Self-Deception and what self-deception means to him

[00:43:39] - Examples of self-deception he underwent that he was able to learn from

[00:46:59] - Mastery and its importance in the world of business

[00:48:59] - Why hippies and APIs may have a tighter correlation than we think 

[00:54:01] - Whether or not technology is fundamentally amoral 

[00:56:10] - Interesting and open questions about the future that remain unanswered 

[00:58:33] - His current creative outlets that he engages with the most 

[00:59:24] - Yahoo Resignation Letter and why he wrote it the way he did

[01:00:31] - Lessons for investors and builders that he’s learned from building Slack

[01:03:07] - The kindest thing that anyone has ever done for him 

[01:04:27] - Why a philosophy primer would be beneficial for virtually everyone

My guest today is Steve Mandel, founder of Lone Pine Capital, one of the most successful hedge fund and investment firms of this generation. In our conversation, we discuss how the investing business has evolved since Steve’s start in the 1980s, why it’s so difficult to drive alpha by shorting stocks today versus 20 years ago, and why Steve still loves to get into the guts of a business. Steve shares his lessons through a variety of great stories, which made this such a fun experience. Please enjoy my conversation with Steve Mandel.

Before we transition to my interview with Steve, I’d also like to highlight the newest Colossus show, Business Breakdowns. If you like Steve’s idea of getting into the guts of a business, this is the show for you. Please find a list of our episodes at joincolossus.com and subscribe to Business Breakdowns on your preferred podcast player.

I hope you enjoy my conversation with Steve Mandel. 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:36] - [First question] - His first encounter with Walmart

[00:05:51] - What about Sam Walton made him worth idolizing 

[00:08:14] - The juxtaposition of business to management quality

[00:10:57] - Why a career in retail influenced the lens he sees the investing world through

[00:11:23] - What bad company culture in retail looks like

[00:12:33] - Aspects of Walmart’s culture that could be applied to other companies

[00:13:54] - Defining the core essence of retail company culture

[00:15:02] - How long it used to take for a stock to properly reflect new information

[00:16:40] - The nature of edge and what it looked like back then

[00:21:09] - Investing behind change and assessing trends

[00:23:06] - Scars and stories from just how vicious short markets can be

[00:26:32] - Thoughts on building an enduring firm and how it’s evolved over time 

[00:32:14] - The process and decision to remove himself from the day-to-day operations

[00:33:55] - Lessons learned over time about what separates good from bad analysts

[00:34:42] - Where to start looking when getting into the guts of a business

[00:36:31] - What is most exciting when you’re inside the guts  

[00:39:19] - Interesting aspects about payments today writ large

[00:42:15] - Broad trends around change in consumer trends 

[00:43:02] - How he views software businesses looking forward as an investor

[00:45:14] - Great managers and their emphasis on analyzing their competitive advantage

[00:48:02] - Ways that pace as a variable has changed in importance

[00:49:27] - What he thinks we’ll look back on as silly in how markets currently operate

[00:50:33] - Whether or not all markets becoming 24/7 will be a good thing

[00:51:59] - Big iconic business stories that newcomers should study

[00:56:06] - Whether or not business building is an art form

[00:57:38] - Key levers that typically always matter for a business

[00:59:53] - Other major aspects of the world that are important to consider

[01:01:13] - How his personal motivations morphed over the years and what has changed

[01:02:55] - Valuable lessons learned about the inputs and outputs of education

[01:04:15] - Advice for would-be future investment analysts

[01:05:46] - The kindest thing anyone has ever done for him

My guest today is Spenser Skates, CEO and co-founder of Amplitude Analytics. Spenser founded Amplitude in 2012 with a thesis that building the best product requires, deep cross-functional understanding of customer behavior. During our conversation, we discuss Spenser’s long history in programming and how his early experiences tie into his work today. We also explore the nuances of equity compensation, how different VCs can play a role in the success of a startup, and Spenser’s desire to see more direct listings vs. IPOs. While many founders follow the path of others, it is clear Spenser takes time to challenge the status quo.

Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. In this episode, you will hear how Spenser’s team worked with the meditation app, Calm, to optimize for customer growth. It was particularly interesting to hear this story after listening to the Calm breakdown. Find episodes of Business Breakdowns on your preferred podcast provider or on joincolossus.com

I hope you enjoy my conversation with Spenser Skates.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to by Dell Technologies. Upgrade your business during Dell Technologies’ Black Friday in July event. Get savings up to 50% off AND take your office with you with Windows 10 Pro. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals.

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. 

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:15] - [First question] - How he won the Battlecode tournament at MIT twice

[00:06:43] - A few key insights that helped him win the tournaments

[00:08:34] - Lessons learned at MIT and the road to starting Amplitude

[00:13:57] - A typical customer experience when using Amplitude 

[00:17:17] - How their platform extrapolates key data points in user data that others don’t

[00:19:03] - His most productive mistakes made while building the company 

[00:21:10] - The strange history of equity and his thoughts on how it should be used 

[00:28:08] - The recent changes in the vesting schedule for newly issued equity 

[00:29:59] - Lessons learned from working with some of the best investors out there

[00:36:20] - His thoughts on the IPO process and going public writ large

[00:41:04] - The role the SEC plays and his perspective on SPACs 

[00:44:01] - Differences in direct listings compared to traditional IPOs 

[00:48:36] - His thoughts on dual-class structures and corporate governance 

[00:50:11] - Hopes for Amplitude as he looks five years into the future

[00:52:03] - The potential value unlock of smart software for end-users  

[00:55:08] - The kindest thing that anyone has ever done for him

My guest today is David Sacks, General Partner at Craft Ventures and founding COO of PayPal. During our conversation, we explore what differentiates Enterprise SaaS from DTC subscriptions, what makes for a magical product launch event, and what key growth metrics David uses to measure success. David has written extensively on his idea of operating cadence, and we explore how that applies to the various functions within an organization. As time goes on, I am more and more impressed at the talent that existed within the original PayPal mafia, and I couldn’t help but ask David to highlight the superpowers for a few of his early partners. This was an incredibly informative conversation with fun threads throughout. Please enjoy my conversation with David Sacks.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick".

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:30] - [First question] - Defining what it means when a company can explode

[00:05:39] - What it would look like if a company didn’t have what it takes to explode

[00:06:17] - Key factors that make for a strong product hook

[00:08:51] - Whether or not there has been a divergence at the early stage of B2B investing compared to B2C

[00:11:36] - Reasons why products that make people collaborate are always stronger

[00:14:14] - Nuances between team subscriptions and team product use

[00:15:37] - Describing the burn multiple metric and how it can be applied to companies

[00:18:18] - The gross margin problem and issues for businesses in this area writ large

[00:22:34] - Common practices amongst sales programs that have and haven’t worked

[00:24:22] - What about new founders makes him most excited

[00:25:58] - Explaining cadence and why he groups product and marketing as one bucket and sales and finance as another

[00:30:44] - The anatomy of a great product launch 

[00:32:17] - Ways in which external dependencies can be landmines for growing companies

[00:34:06] - Whether or not he’s willingness to invest in a business with regulatory variables

[00:36:59] - What he’s seen in company culture that breaks a company as they scale

[00:39:55] - Things a founder actually does in order to reign in and tame their culture

[00:42:08] - Unique traits of founders who are both investors and operators

[00:44:12] - Peter Thiel’s superpower 

[00:44:57] - Max Levchin’s superpower

[00:45:38] - Elon Musk’s superpower

[00:46:07] - Roelof Botha’s superpower

[00:47:15] - Reid Hoffman’s superpower 

[00:47:43] - Keith Rabois’ superpower 

[00:48:41] - What zones of change in the world have his attention writ large

[00:51:43] - Why teams want to be pushed and how we can apply that to business

[00:55:25] - The kindest thing anyone has ever done for him

My guest today is David Vélez, founder and CEO of Nubank, the world’s largest digital bank with over 40 million customers. In our conversation, David talks about his venture capital background at Sequoia and how that led him down an entrepreneurial path in Latin America. We also talk about the pros and cons of building a digitally native business and what gets him most excited about innovation and technology in emerging markets.

Before we start the episode, I would also like to highlight our newest Colossus show, Business Breakdowns. Since launching in early April, we have published over 15 Breakdowns and continue to release a new episode weekly. To learn more, check out joincolossus.com. I hope you enjoy my conversation with David Vélez.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. 

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:55] - [First question] - Why Berkshire Hathaway took such an interest in Nubank

[00:04:46] - Key differentiators between Nubank and other incumbent banks

[00:07:11] - Onboarding user experience and overview of customer acquisition

[00:10:38] - The original problem Nubank wanted to solve and how they approached it

[00:15:32] - Lessons from working at Sequoia about great FinTech businesses

[00:19:18] - What parts of his personality and life experience worked its way into NuBank

[00:23:18] - Obstacles that needed to be overcome in order to serve the Brazilian public

[00:27:52] - Transparency and patience needed to overcome a complicated problem

[00:31:11] - Nubank’s business economics compared to other banks

[00:34:46] - Overview of rewards programs and why customers like them so much

[00:37:27] - Best questions asked that explained Nubank’s market opportunity

[00:42:02] - Second layer unit economics of the company and where to look for them

[00:45:51] - How far we are into the Latin American technological ecosystem’s development

[00:47:24] - Lessons learned from some of the worst decisions he’s made as a founder

[00:51:30] - What he’s most excited about for the future

[00:54:19] - The kindest thing anyone has ever done for him

My guest today is Balaji Srinivasan, a serial entrepreneur and angel investor. Balaji is known to challenge conventional wisdom, and he lives up to his reputation in this conversation. We discuss a wide variety of topics, including advancements in health tracking, ways to evaluate your own information diet, and how technology is driving decentralization and what that could mean for countries, corporations, and individuals.

Before we transition to the episode, if you enjoy this conversation with Balaji, I’d recommend the Ethereum episode on our newest show, Business Breakdowns. You can find that episode and more on your favorite podcast player or at joincolossus.com. Please enjoy my conversation with Balaji Srinivasan.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Marqeta, Oatly, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

------

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick".

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:30] - [First question] - Thoughts on information diets and how they influence individuals

[00:21:37] - Ways to optimize your diet by reading the source material and consuming less news

[00:26:40] - Understanding the informational supply chain and tracing data back to the origin

[00:41:07] - Modern cities, the nature of a group of individuals, and what sovereignty may mean in the coming years

[00:53:52] - Key ingredients and main components needed for a successful startup city

[01:11:35] - Social impacts from everyone becoming an investor and how it ties into everything

[01:25:49] - Recommendations and a personal prescription for longevity, health, and wealth

[01:37:32] - The kindest thing anyone has ever done for him

My guest today Michael Mayer, is the founder and CEO of Bottomless, a company that automatically replenishes your coffee supply where I am both an excited investor and customer. Today’s conversation is about tactical lessons Michael has learned while building the business. We talk about identifying an addressable problem, how to avoid solving for bottlenecks that don’t yet exist, and how to iterate through problems before scaling. As yet another example of a self-taught entrepreneur, it’s inspiring to hear Michael’s mindset for problem-solving. I hope you enjoy my conversation with Michael Mayer. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to by Dell Technologies. Upgrade your business during Dell Technologies’ Black Friday in July event. Get savings up to 50% off AND take your office with you with Windows 10 Pro. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals.

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA, or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. 

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:45] - [First question] - How he got into this space in the first place and found the problem Bottomless would eventually solve

[00:08:43] - What he would do better the second time if he had to find a problem and narrow his focus all over again

[00:09:49] - The most notable lessons learned about data legibility beyond the scale

[00:10:15] - Seeing like a State: How Certain Schemes to Improve the Human Condition Have Failed

[00:13:01] - Overview of building the first Bottomless hardware prototype 

[00:14:29] - First steps of physically assembling the first scale and learning fabrication

[00:17:40] - Roughly how long it would take to build scales in the beginning

[00:18:30] - How long the company was bootstrapped 

[00:20:41] - Making the pivot to seeking out investor support

[00:29:03] - The often overlooked role of social capital as a startup founder

[00:31:00] - Importance of following niches and passions

[00:32:15] - His philosophy in successfully scaling the production side of the company

[00:34:45] - Lessons learned from bottlenecks and their utility in founder growth

[00:36:52] - The problem of supplier legibility and improving it

[00:40:14] - Understanding USPS predictability as a product input

[00:43:03] - Always problems to solve and the fractal nature of them

[00:46:13] - Challenges of hiring staff in the tech space

[00:50:15] - Lessons learned about personal bottlenecks and the need to evolve alongside your company

[00:52:21] - Monitoring your informational inputs and their role in shaping your mindset

[00:55:58] - Closing thoughts on the business boss battles founders face

[00:57:38] - Why society writ large should perceive starting a company as status-enhancing

[00:59:44] - What bottlenecks for Bottomless may present themselves in a year from now

My guest today is Silicon Valley icon, Marc Andreessen. Before co-founding the legendary venture capital firm, Andreessen Horowitz, Marc was an early pioneer of the internet. At age 22, he built Mosaic, the first widely adopted web browser and the technology that underpinned Netscape Communications. Marc was an early proponent of cloud computing, social networks, and the software business model. In each case, Marc seemed to be well ahead of the crowd. During our conversation, we explore how software is making the world better, how slow sectors like education, healthcare, and housing are eating the economy, and Marc’s vision of the future for A16Z. Please enjoy my conversation with Marc Andreessen.

Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. Each week we do a deep dive into an individual business to understand what makes it great. Find more information on joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player.                                        

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:04:10] - [First question] The ways in which software is eating the world

[00:06:25] - The power of transitioning from atoms to bits and its impacts

[00:09:57] - Potential downsides and credible concerns as we shift into an automated world 

[00:16:00] - Major impediments of productive growth over the coming decades  

[00:23:12] - Real change versus false change due to COVID-19 writ large 

[00:30:06] - Thoughts on the rising cost of post-secondary education in light of the internet

[00:37:03] - Why doesn’t Google have their own university and if they might in the future

[00:41:30] - Whether or not an entrepreneurial focus on generally slower sectors may produce excess returns

[00:44:17] - Thoughts on hardware, its unit economics, and its role in shaping society

[00:47:52] - How to think about investing in immensely complicated, large-scale projects

[00:54:10] - What they’re building at A16Z, a new crypto fund, and where their sights are set

[01:03:09] - East coast investing styles and things we can borrow from them

[01:06:01] - Potential plans to step into the public equity space 

[01:11:09] - Defining why it’s time to build and the imperative it sets

[01:15:13] - The kindest thing anyone has ever done for him

My guest today is Will Ahmed, founder of fitness wearable company WHOOP. What started as a business plan in 2011 has evolved into the 24/7 health-tracking device you’ll often see on athletes across professional sports. During our conversation, Will and I discuss how his own backstory ties into the founding of WHOOP, the key design decisions they made in the ultra-competitive wearables market, and how the company grew slowly before inflecting in recent years. Will shares awesome details on health tracking and what it might look like in the future as a preventative tool rather than simply a tracking tool. I hope you enjoy this great conversation with Will Ahmed.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders.

-----

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick."

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:45] - [First question] - The founding story of WHOOP

[00:05:45] - Narrowing in on the problem to focus on solving 

[00:08:58] - Overview of analyzing and quantifying recovery, strain, and sleep

[00:15:52] - Downsizing the problem set to deliver an affordable solution

[00:18:48] - What he’s learned about hardware product road mapping

[00:21:43] - How many people wear their WHOOP all-day

[00:22:05] - Early lessons from taking their wearable tech product to market

[00:26:25] - Ways in which they landed their first high-profile athletic brand ambassadors

[00:27:55] - Interesting methods that proved successful in their marketing tactics

[00:32:06] - Observations of making the switch to a subscription service

[00:34:00] - Why big apparel companies failed where WHOOP didn’t

[00:35:20] - Changes in behavior from users who learn about their habits using WHOOP

[00:40:18] - His philosophy on business partnerships and how he developed it

[00:44:56] - How he ended up with a paddle from the Navy Seals

[00:47:13] - Ways WHOOP stays ahead and upcoming trends in the wearable tech space

[00:50:13] - Data beyond HRV that will become more accessible and affordable to track 

[00:51:09] - The extent that data and software relative to hardware are a key part of WHOOP

[00:53:06] - Lessons learned about effective leadership on a personal level

[00:56:13] - Notable differences in his leadership style from then compared to now

[00:57:34] - Thoughts about business defensibility in such a competitive space

[00:59:44] - Reasons behind why WHOOP products don’t have a screen

[01:02:13] - Valuable lessons for other entrepreneurs when studying WHOOP’s story

[01:05:03] - Systems in place that allow for their speed and pace of growth

[01:06:31] - What makes a day of work fun for him

[01:08:39] - Why we shouldn’t measure our steps

[01:10:01] - What is the kindest thing anyone has ever done for him

My guest today is Howard Marks, co-founder of Oaktree Capital, a leading investment manager, and one of the world’s largest distressed debt investors. In our conversation, we discuss takeaways from the market selloff and rapid recovery in 2020, the importance of assessing both quantitative and qualitative factors in markets, and the benefits Howard has realized from a career of writing. I hope you enjoy this great conversation with Howard Marks. 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

------

This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:40] - [First question] - Ideas he has that he feels will stand the test of time

[00:04:39] - Defining the difference between risk and uncertainty and a frame of mind to have around uncertainty as an investor

[00:05:31] - Equity and debt investing as the businesses of what could go right or wrong

[00:07:01] - How exciting equity up runs can lead to analytical blindspots

[00:09:10] - Ways in which the last 18 months stacked up against his market experience

[00:11:57] - Ways we can change our model of the world going forward to avoid a crisis

[00:15:04] - Why psychology is important to consider over data during market extremes

[00:17:46] - Reflections and lessons from discussing the concept of value with his son

[00:27:33] - Spirited disagreements he and his son continue to have about markets

[00:31:46] - What he’s learned about writing well and the utility of doing so

[00:40:39] - Lessons that are better experienced in investing than reading about them

[00:43:35] - Daring to be great and the willingness to be wrong, alone or different

[00:50:24] - Embracing mystery and the joys it can bring

[00:53:28] - The kindest thing anyone has ever done for him

My guest today is Christina Cacioppo, founder of Vanta, a security and compliance software business founded in 2017. In our conversation, Christina brings to life the idea of “finding a problem that exists and fixing it.” We dive into the experiences that led her to launch Vanta, the strategy she took to build, price, and distribute the product, and we touch on her lessons from running a growing organization. I always admire the drive that founders have when they set off to build something -- Christina fits that mold, and you will hear about how she embarked on a self-taught journey early in her career. I hope you enjoy my conversation with Christina.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:44] - [First question] - How she first found her interest in business

[00:04:09] - Early days exploring business for the first time

[00:07:09] - Lessons learned from USV that have been applied to Vanta

[00:07:42] - The next stage of her learning journey after USV

[00:09:20] - Making a massive pivot in life and teaching herself to code

[00:10:53] - The four-year road that lead to building Vanta

[00:12:39] - First encounters with the software security problem space

[00:15:21] - Origins of SOC 2, what it means, and what it does

[00:17:11] - What software security means writ large

[00:19:32] - Who demands a SOC 2 and why

[00:20:57] - How Vanta improved a broken process and productized it

[00:23:33] - What V1 of Vanta looked like

[00:26:30] - Understanding the value of using spreadsheets first

[00:27:48] - From static to streaming and finding product-market fit

[00:29:22] - Monitoring whether or not a company is SOC 2 compliant in real-time

[00:32:19] - Auditors that still exist in the compliance space today

[00:33:39] - The pace of onboarding new clients onto the Vanta software 

[00:34:53] - Figuring out a price point for the service Vanta offers

[00:37:06] - Developing the business model and scaling it

[00:39:18] - Lessons learned and innovations created about effective sales organization

[00:41:52] - Hardest hills to climb in building Vanta

[00:43:17] - Building competitive advantage into the framework of the business

[00:46:07] - Overview of the frontier of software security

[00:47:43] - General thoughts on competitive advantage as a whole

[00:49:43] - Quality control of decision making in Vanta

[00:50:40] - Downstream effects of structural and organizational business design

[00:52:30] - Hard lessons learned going from being academic to pragmatic

[00:53:36] - What the future could look like for Vanta based on its current trajectory

[00:54:26] - What her information diet consists of lately 

[00:55:27] - Areas she’s interested in currently but learning more than being proficient 

[00:56:59] - Ways in which she’s become a better leader

[00:57:46] - Unique factors about what makes Vanta tick

[00:58:45] - Negative advice to would-be founders out there

[01:00:22] - The kindest thing anyone has ever done for her

[01:02:44] - Major insights learned from living in Rwanda, Thailand, and Uganda

My guest today is John Harris, Managing Partner of Ruane, Cunniff & Goldfarb, where the flagship Sequoia Fund has an incredible 50-year track record running a highly concentrated portfolio of equities. In our conversation, we cover John’s approach to finding businesses that can be owned for the long-term, what goes into their diligence process, and the importance of resilience for investors. I think many of the stock pickers will enjoy many of the points on good management, good businesses, and using imagination. I hope you enjoy my conversation with John.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

------

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

------

This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:48] - [First question] - How markets undervalue long-duration growth of companies

[00:07:21] - Why should one even do DCFs at all

[00:10:01] - Defining homework when studying a business and what getting better as you do your homework tends to look like

[00:12:24] - How the market still underestimates how the quality of a company reduces risk

[00:15:09] - Reinvestment opportunity and risk and why they’re important for long term returns

[00:17:14] - Lessons learned owning Google stock options for over a decade

[00:22:02] - Skill versus luck when it comes to investing psychology

[00:24:32] - Perspectives on big market cap companies in a portfolio when success often comes from smaller-cap non-linear growth 

[00:26:47] - Features of the current market landscape that he finds interesting

[00:31:24] - What buying behavior looks like in the demand side of the business equation

[00:34:10] - Discovering a company that served the customer and was a delight to discover

[00:37:58] - Analysing getting one's hands dirty to get a competitive advantage in serving the customer

[00:39:24] - The hardest episode of his investing career and what he learned from it

[00:43:03] - Reasons why a company succeeded after doing a deep dive but not buying in

[00:43:54] - One of the CEOs he finds most remarkable

[00:47:20] - Examples of businesses where scale isn’t the driver of competitive advantage

[00:49:50] - A company they owned that did well but didn’t have the strongest company culture

[00:50:56] - His view on the investment industry today writ large

[00:52:16] - Ways investors could expand their imagination when analyzing businesses

[00:53:07] - The kindest thing anyone has ever done for him

My guests today are Florian Hagenbuch and Mate Pencz, co-founders of Loft. Based in Sao Paulo, Brazil, Loft is a digital platform designed to bring Latin American real estate into the e-commerce age. The 3-year-old startup scaled to over $150mm in annualized revenue in 2020 and is on track for multiples higher this year. We dive into the market opportunity in Brazilian real estate and how that differs from the US market, the value proposition for iBuying across the US and Latin America ecosystems, and touch on the potential for Loft to expand from real estate into adjacent services such as mortgages. Florian and Mate are second-time founders and have some great lessons shared throughout the episode. Please enjoy my conversation with Florian and Mate.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders.

-----

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick."

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:52] - [First question] - Why Latin America currently presents such a unique opportunity for modern technology companies

[00:04:38] - What the market looked like when they started Loft

[00:07:20] - How they approached gathering data that wasn’t available or accessible in order to develop the company infrastructure

[00:09:39] - How the process of buying a home used to be in São Paulo versus today

[00:12:19] - What Loft’s hard work unlocks for consumers and home buyers

[00:14:06] - What iBuying feels like writ large and more specifically in real estate

[00:18:07] - Analysis of an iBuying real estate transaction from start to finish

[00:20:09] - The role machine learning plays in property valuation and building that feature  

[00:22:50] - Defining their business model and being a fulfillment center aggregator 

[00:24:47] - Notable characteristics of the iBuying market in the United States 

[00:27:00] - How they think about the competitive advantage extensions of Loft 

[00:29:53] - Exciting opportunities for the FinTech broadly in Latin America 

[00:32:47] - Deciding on what it is they want to tackle next as they grow the company 

[00:34:13] - Thinking about the value proposition to customers and how they market it 

[00:35:50] - Lessons learned about building businesses early on that were applied to Loft

[00:40:12] - What led them to finding their early product-market fit 

[00:42:48] - Calibrating and defining their ambitions for Loft out of the gate 

[00:45:05] - Important and interesting trends in the business world today writ large 

[00:48:43] - Further lessons and key challenges around building and scaling Loft 

[00:52:24] - The kindest things that anyone has ever done for them

My guest is Gabe Leydon, who is the co-founder and former CEO of MZ, also known as Machine Zone, the company behind huge games such as Mobile Strike and Game of War. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I have talked to in a long time. In our conversation, we cover why great design can be a bad sign that we’d run out of ways to innovate, the most important lessons from human psychology for building games and products, and why products which are busted or breaking but still booming can be great investment opportunities. This conversation rewired my brain on many levels, so I’m excited for you to listen. Take the red pill with us, and please enjoy my conversation with Gabe Leydon.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

------

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

------

This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:59] - [First question] - Thoughts on the importance of design and the role it plays in capitalism writ large

[00:07:26] - Huxley’s vision of the future versus Orwell’s - Amusing Ourselves to Death

[00:10:49] - A question about game design in interviews that no one can answer well

[00:18:27] - What about his early experiences that allowed him to be good at answering that question when others could not

[00:26:35] - Another example to further explain the nature of meta software design mechanics

[00:29:44] - Characteristics of what drives players to spend money in games

[00:34:46] - Defining heroic spending and the group dynamics of spending gamification

[00:38:18] - Skill set required to design an economy and what makes it so difficult

[00:41:27] - Cosmetic purchases as a revenue stream in North American video games

[00:43:56] - What he’s learned about human psychology through his design work

[00:45:48] - How the technological infrastructure developed in building video games overlap in performance marketing

[00:48:44] - His experience with the RT platform and some of the technologies he’s built

[00:55:49] - Celebrity NFTs and a shift to becoming virtual manufacturers in the future

[00:59:58] - What businesses can do now to prepare for and adapt to NFTs

[01:01:03] - Why we need AI more than think we might

[01:04:32] - What he plans to do with his skillset if the world becomes increasingly gamified

[01:05:40] - Companies with poor design may be indicative of an attractive acquisition

[01:08:11] - How differing cultural perspectives on video game design permeate into NFTs

[01:08:46] - Defining the Chinese item box approach to in-game player rewards

[01:11:24] - The kindest thing that anyone has ever done for him

My guest today is Assaf Wand, CEO, and co-founder of Hippo, a homeowner insurance startup founded in 2015. In March 2021, Hippo announced a SPAC merger, valuing the business at over $5bn. In our discussion, we cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners has opened up Hippo's business model to a wide range of opportunities. I was excited to speak with Assaf, given his experience as a serial entrepreneur, and he did not disappoint. Please enjoy my conversation with Assaf Wand.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.

See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders.

-----

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick."

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:44] - [First question] - His philosophy on business

[00:04:04] - His first experience in entrepreneurship

[00:05:03] - Lawyers vs entrepreneurs

[00:07:03] - Major lessons taking risk in entrepreneurship

[00:11:14] - Importance of speed in business

[00:15:02] - Increasing urgency into the business as a leader

[00:18:59] - What the insurance sector was like at the start of Hippo

[00:24:49] - Steps he took to bootstrap trust

[00:27:03] - Convincing partners

[00:29:04] - Building the products and distribution

[00:32:49] - Thoughts on innovators dilemma

[00:35:00] - Flaws within the insurance industry

[00:34:57] - Vision for the firm 

[00:37:44] - Importance of culture in company building

[00:41:19] - Storytelling as an essential piece of company building

[00:41:50] - Building and managing a roadmap

[00:43:19] - What does it mean to respect the customer

[00:46:11] - Defensibility of the insurance industry

[00:49:34] - Rewards of the trench warfare of entrepreneurship

[00:53:33] - The feeling of getting wealthy 

[00:55:29] - Kindest thing anyone has done for him

My guest today is Dennis Lynch, Head of Counterpoint Global, where he oversees over $100bn in AUM and boasts one of the strongest track records of any public investor. In our conversation, we cover Dennis's unique approach to building a research team, how misclassification of companies often creates the highest upside opportunities, and how Dennis has adapted his investment process over the past 20 years. I think Dennis defines what it means to be intellectually honest, and you will hear that in his answers throughout our discussion. I hope you enjoy my conversation with Dennis Lynch.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

(for me-  )

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

------

This episode is brought to you by MIT Investment Management Company (MITIMCo), the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term.

MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:47] - [First question] - How he would teach potential students to be investors

[00:04:26] - The Money Game

[00:04:40] - Moneyball

[00:05:59] - Pros and cons of volatility when investing

[00:08:55] - Emotional response to volatility

[00:12:44] - Training to have a better temperament

[00:14:20] - What is his investing game

[00:15:17] - The Ethical Algorithm

[00:16:44] - How time horizon impacts their investment strategy

[00:20:53] - Assessing a company’s earnings power

[00:26:12] - Shifting business models vs. evolving within a business model

[00:32:32] - Understanding how to invest in disruptive businesses

[00:35:26] - Why he’s skeptical on Growth and Value investing strategies

[00:38:42] - Expectations Investing

[00:38:55] - How his view of assessing businesses has changed

[00:43:56] - Defining unit economics

[00:45:41] - Taking on uncertainty risk in the portfolio 

[00:50:38] - The business that taught him the most; Amazon

[00:53:32] - Dealing with massive amounts of change

[00:56:01] - The Big Short

[00:59:46] - Interest in psychedelic research

[01:01:02] - What has changed the most in investing from when he started

[01:04:19] - Kindest thing anyone has done for him

My guest today is Henrique Dubugras, co-founder and CEO of Brex, an all-in-one finance account for businesses. Brex recently raised funding at a valuation of over 7 billion dollars despite being founded only four years ago. In our conversation, we cover Brex’s transition from a credit card for start-ups to the central account for businesses, why building that central account was orders of magnitude more difficult than expected, and the difference between building a business in Brazil and the US. We also discussed Henrique’s term horizon for building Brex and how that impacts his decision-making for the business. Please enjoy my conversation with Henrique Dubugras.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:53] - [First question] - The state of the B2B financial world before Brex

[00:06:29] - How such a high margin space was generally underserved

[00:08:24] - What the first version of the Brex card looked like

[00:10:48] - How long it took to build and launch their infrastructure

[00:11:13] - Why market penetration is so low for cards in B2B businesses

[00:13:14] - How he thinks about this landscape in Brazil versus the US

[00:14:55] - What interchange and high margins allows him to pass on to the consumer

[00:16:23] - Brex’s first revenue event

[00:17:38] - What the biggest hurdle was to overcome when they launched

[00:19:02] - Key marketing strategy early on and what made it successful

[00:21:16] - Continued distribution lessons they learned from their initial success

[00:22:39] - Building an effective sales force to push their product

[00:24:41] - What makes the current landscape so fertile for fintech businesses

[00:27:12] - Analysis of their unique funding round dynamics

[00:28:42] - Their second product and the insight that lead to that decision

[00:31:05] - Darkest moments while trying to build their central account

[00:31:50] - What their central account allows them to facilitate writ large

[00:35:27] - Notable differences between entrepreneurship in Brazil versus the US

[00:38:55] - Observations on inefficiencies in the US startup space

[00:40:16] - Pros, cons, and costs of being largely remote

[00:41:50] - Keys to building a successful hiring pipeline

[00:44:05] - Lessons learned about decision making and optimization

[00:45:39] - Developing an effective skill set to convince other people of anything

[00:47:35] - What excites him about being a part of Brex lately

[00:49:13] - What excites him about the future in general

[00:50:39] - His business philosophy and the set of principles that guide him 

[00:52:03] - Nuances that make focusing on a single problem so attractive

[00:53:51] - Long term infrastructure decisions that will pay off in the end

[00:55:12] - Thoughts and hi perspective on cash flow in general

[00:58:18] - The kindest thing anyone has ever done for him

My guest today is Justin Fishner-Wolfson, founder of 137 Ventures, a venture capital fund focused on providing liquidity solutions to founders, investors, and employees of private businesses. In our conversation, we discuss what early career experiences led Justin to start 137 Ventures, the counter-intuitive information asymmetry between public and private markets, and the interesting trend of digitization in the physical world. I hope you enjoy my conversation with Justin.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:47] - [First question] - Why he started 137 Ventures and what’s unique about it

[00:05:31] - Overview of secondary equity markets in the tech sector

[00:07:06] - Step by step process of how a secondary market investment works

[00:09:37] - Scale of secondary transactions in markets today

[00:10:19] - Valuations of secondary transaction rounds versus primary ones

[00:11:37] - Defining great in private market investments and the competitive landscape

[00:13:13] - Why there seems to be more information available in private markets

[00:16:23] - How better capital allocation may result from less asymmetry

[00:19:14] - What excites him about companies when meeting them for the first time

[00:20:34] - Example of applying his philosophy of investing in a defensible business

[00:22:20] - Counter positioning and inversion models to gain an advantage

[00:24:17] - Lessons learned from Palantir about unlikely competitive advantage 

[00:25:57] - Building good businesses when selling them to the government

[00:26:59] - What technology means in the current era

[00:28:34] - Methods for evaluating potential sources of defensibility and a lack thereof

[00:30:30] - Considering focus and expansion when scaling

[00:32:52] - Shared qualities of entrepreneurs who build these types of businesses

[00:33:50] - The business that individually taught him the most writ large

[00:35:01] - Defensabilities that might appear beyond the seven powers framework

[00:36:21] - Thoughts on what seems to be craziest in the world today

[00:37:15] - What’s surprising on the low end of the valuation side

[00:38:11] - Interesting business models and ones he’s averse to 

[00:40:31] - Constructing a portfolio with companies that have a customer focus

[00:41:21] - Additional companies in their portfolio that aren’t of a similar model 

[00:42:08] - Lessons learned from SpaceX’s growth

[00:44:46] - Watching a SpaceX launch in person

[00:46:03] - Advice for entrepreneurs when seeking capital and capital partners

[00:48:04] - Investors he finds most impressive that he knows well

[00:49:26] - Defining the cost of capital and what it means to him as a venture investor

[00:50:56] - Is giving entrepreneurs too much money dangerous?

[00:54:14] - What great capital allocation looks like to him

[00:55:29] - Accelerating learning curves with tighter feedback loops

[00:55:57] - Useful metrics for customer acquisition and retention

[00:57:06] - Whether or not investing firms can and should behave defensibly

[00:59:13] - What is going in the world that has his attention lately

[01:02:06] - Key factors that have allowed him and his firm to succeed

[01:03:47] - What he thinks about when his mind isn’t focused on investing

[01:04:08] - The kindest thing anyone has ever done for him

My guest today is Peter Reinhardt, co-founder and CEO of Segment, the market-leading data customer data platform that was acquired by Twilio last year. In our conversation, we cover the fascinating journey of Segment from an education feedback tool to the business it is today, Peter’s sales philosophy on meeting the customer where they are and not where you think they should be, and why revenue operations, or RevOps, is underrated for any business. This was an incredibly honest conversation on company building that any builder can learn a lot from. Please enjoy my conversation with Peter Reinhardt.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:47] - [First question] - What Segment currently does for its customers

[00:03:37] - How this industry looked before Segment came along

[00:04:30] - Overview of a simple data flow and the utility of capturing user data

[00:05:55] - Insights that lead to developing the structure for a central data pipeline

[00:07:52] - Why other companies don’t just build their own data collection API

[00:10:04] - Early days of building the company and finding success outside their initial idea

[00:12:29] - Pivoting from classroom software to providing software the world needed

[00:16:17] - What Technology Wants 

[00:17:06] - Sign that validated becoming a B to B software company

[00:19:49] - Challenging moments trying to scale Segment after bootstrapping the startup

[00:24:58] - Getting customers to articulate your value proposition helps grow your sales

[00:26:42] - Deciding what would be sold and what would remain open source

[00:28:05] - Structuring and developing an enterprise sales team and sales model

[00:30:23] - Overview of a 2 million dollar per sales person contract and how it’s allocated

[00:31:38] - How it feels to be participant in the SaaS industry

[00:34:02] - Lessons learned about revenue operations and how underappreciated it is

[00:36:39] - Backwards efficiency and companies who use products to bootstrap scale economics

[00:38:51] - Focusing on customer acquisition cost to maximize scale efficiency

[00:40:52] - Potential disruptors to economies of scale

[00:42:21] - Lessons learned from achieving massive scale and being acquired by Twilio

[00:45:40] - Behind the curtain view of current data use trends

[00:48:49] - His perspectives on the data privacy landscape and their implications writ large

[00:51:48] - Legitimate businesses that will be hurt by changes in data privacy standards

[00:53:11] - How data privacy standards may affect everyday merchants

[00:54:03] - The worst advice he’s heard given to new entrepreneurs

[00:56:20] - Impactful advice received along the way when growing Segment

[00:56:47] - What has him most excited about the future

[00:57:13] - Lessons learned about leadership from Jeff Lawson and his own experience

[00:58:51] - The hardest changes he’s had to make as a leader

[01:00:20] - The kindest thing anyone has ever done for him

My guest today is Brent Beshore. For those that don’t know Brent from his frequent appearances on this podcast, he runs Permanent Equity Fund and has been a close personal friend for the past five years. Brent and I revisit our conversation from the heart of COVID to touch on key lessons learned and where that leaves us today. Brent sits at a unique touchpoint of the economy, so I particularly enjoyed his anecdotes on inflation and how to operate around these dynamics. I hope you enjoy my conversation with Brent.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:52] - [First question] - Why last year ended up being so bullish

[00:07:14] - Deal dynamics of the current landscape

[00:09:54] - Lessons learned about managing a team through the pandemic

[00:14:39] - Observations on the housing market and the pool industry

[00:18:56] - Current labor force dynamics of trades 

[00:21:18] - Considering labor dependency when investing in new businesses

[00:23:10] - His perspectives on the future of tech through his investment lens

[00:25:50] - Seeking out traditional businesses that reinvent age-old frameworks 

[00:27:50] - Key stages of the art and science of evaluating and acquiring a company

[00:31:45] - How much information he wants to know before making an initial offer

[00:34:25] - Psychology of structuring and aligning incentives post-acquisition 

[00:37:41] - What defines a great deal negotiator

[00:40:05] - His most creative act when structuring a deal that didn’t work out as well

[00:42:17] - Hist most creative structuring act that proved useful for the upside

[00:43:34] - Notable changes in large-cap private equity markets

[00:45:41] - Skills he feels he can improve on over the coming five years

[00:48:30] - Coaching small companies on how to recruit top tier talent

[00:52:49] - How to effectively get people to say yes to job offers and openings

[00:54:19] - Absolute and relative changes in the opportunity set of small to mid-cap markets

[00:57:40] - Lessons learned from strong support networks and onramps of upward mobility

My guest today is Jeremy Cai, founder, and CEO of Italic, a subscription marketplace for consumer goods that works directly with manufacturers. I was introduced to Jeremy by my friend Blake Robbins and was dying to better understand the Italic business model. In our conversation, we discuss the Italic business model, the evolving role of manufacturers in supply chains, and the concept of building the next generation “everything store.” I love learning and discovering new business models, and this was fun to dig into. Please enjoy my conversation with Jeremy Cai.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals.

-----

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick."

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:45] - [First question] - Overview of Italic’s business model

[00:04:51] - Why comparing Italic to Costco isn’t completely accurate

[00:10:06] - His initial experience with manufacturers and how that world works

[00:15:21] - Direct to consumer commerce and the power of a brand’s story

[00:20:06] - Where manufacturers find the cash to effectively manage their inventory

[00:25:26] - How design and R & D are handled by manufacturers in the current era

[00:29:36] - Educated consumers and emotional versus rational buying decisions 

[00:31:12] - Analyzing Italic’s five-step master plan and what needed to be built first

[00:35:42] - Becoming more than just an aggregator and a platform

[00:38:01] - Lessons learned from building Italic so far

[00:39:02] - Other modern business models he finds interesting

[00:43:26] - What Not Pot is and lessons learned from building it

[00:44:51] - Observations about consumer behavior in his managed marketplace

[00:48:07] - The kindest thing anyone has ever done for him

My guest today is Eli Dourado, economist and senior research fellow at the Center for Growth and Opportunity at Utah State University. In our discussion, we touch on the ongoing stagnation in labor productivity, the system constraints, and some of the innovative technologies that could reverse this trend. While Eli identifies as an economist, his wealth of knowledge on biotech innovation, alternative energy, and the space opportunity are sure to leave you craving more. I hope you enjoy my conversation with Eli. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:28] - [First question] - Why he’s interested the great stagnation

[00:05:41] - Is a fair analog for total factor productivity technology?

[00:07:29] - Leading theories for the stagnation in TFP

[00:09:05] - Analysis of why growth is good, and stagnation is bad

[00:10:19] - Rate limiters that are a key part of calculating stagnation

[00:11:43] - Signs that we may be returning to a higher degree of TFP returning

[00:12:24] - Exciting developments like MRNA in biotech that may lead to an explosion of innovation

[00:16:16] - Functions of a protein and their role in advances in biotech

[00:17:55] - What CRISPR is and what it unlocks for the future of humanity

[00:19:31] - The pace of progression when rolling our clinical trials of cellular engineering

[00:21:36] - How biotech may play a role in TFP as a proxy for progress and growth

[00:22:51] - Interesting observations about potential innovation in the energy sector

[00:24:10] - What currently requires energy that could be optimized if they had a lower energy cost

[00:25:34] - Sources that could provide cheaper and more efficient energy

[00:27:13] - Sage Geosystems and the future of the geothermal space

[00:27:43] - The importance of batteries in the modern era

[00:29:02] - Why energy should be a more pivotal focus in our future

[00:29:41] - What’s interesting in the world of transportation writ large

[00:31:02] - Boom’s story, supersonic air travel, and why concord shut down

[00:34:55] - Mach 5 and March 12 supersonic air travel

[00:36:19] - Second-order effects of reducing the time cost of air travel

[00:38:19] - Liftoff, SpaceX, and the future of the space sector

[00:43:07] - Other key players in space people could study; Blue Origin and Relativity Space

[00:45:15] - What will we do in space once we can travel there cheaply

[00:46:39] - What he’s most curious about in IT that could drive productive societal growth

[00:50:07] - Ethereum and how a decentralized blockchain could change the world 

[00:51:19] - The kindest thing anyone has ever done for him

My guest today is James Reinhart, founder, and CEO of thredUP, an online thrift marketplace. thredUP’s online store is distinct in the way the company touches every product, processing every piece of clothing at their own facilities instead of focusing solely on being a marketplace connecting buyers and sellers. We talk about the competitive advantages of building processing plants from the ground up, how James turned thredUP from having negative gross margins to very strong unit economics, and the future of retail more broadly. I hope you enjoy this conversation with James Reinhart.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals.

-----

This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick."

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:47] - [First question] - An overview of thredUP

[00:03:44] - Origination of the idea

[00:04:43] - Initial reactions to the concept

[00:05:22] - Early days trying to acquire the first customers

[00:07:32] - The evolution of their margins

[00:11:04] - Providing convenience for the customer

[00:13:01] - Lessons on working capital and inventory 

[00:14:27] - How consumers use the money they receive within the platform

[00:15:47] - The evolution of the operations of the business and scaling

[00:20:20] - When it’s time to shift from human capital to automation

[00:22:00] - The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time

[00:22:39] - Competitive Advantage: Creating and Sustaining Superior Performance

[00:23:15] - Removing the hurdles for acquiring more buyers 

[00:27:19] - Convincing investors on this concept

[00:30:44] - The most difficult time for him psychologically in creating the business

[00:31:56] - How he thinks about capital allocation

[00:32:12] - The Startup Way: How Modern Companies Use Entrepreneurial Management to Transform Culture and Drive Long-Term Growth

[00:33:51] - Overview of the clothing landscape and what would surprise most people

[00:38:00] - Expanding their business from here 

[00:40:36] - Improving how the raw material is sourced for apparel

[00:42:45] - The nature of work 

[00:42:56] - Dustin Moskovitz Podcast Episode

[00:49:04] - What he’s most excited about for the future

[00:50:35] - Kindest thing anyone has done for him

My guest today is Andrew Sugrue, co-founder, and partner at Avenir Growth Capital. Avenir is a growth equity firm focused on backing category-defining businesses. In our conversation, we cover Andrew’s investing career, what he learned from Julian Robertson, how counter-positioning could drive unique distribution, and the difference between good and bad growth. We also spend time examining the business model of two of Andrew’s portfolio businesses, SavageXFenty and Latch. There are so many great lessons for investors and operators to take away from Andrew. Please enjoy my conversation with Andrew Sugrue.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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This episode is brought to you by MIT Investment Management Company – MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. 

MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:31] - [First question] - His journey leading up to his current firm

[00:05:55] - Lessons learned from time spent with Julian Robinson

[00:07:54] - The chip on his shoulder that helped keep him driven

[00:08:40] - Transforming his early motivators into a sustainable career-long fuel

[00:10:46] - The first things in mind when approaching a new business or person

[00:14:00] - Analysis of Savage Lingerie and learning about how that sector operates 

[00:20:27] - Amazon producing a one-hour special Savage infomercial 

[00:23:16] - Lessons learned from Savage that can be applied to other direct to consumer brands

[00:25:04] - Having a celebrity at the forefront of your brand

[00:26:41] - Levers and overview of apparel company income statements and how they can shape the way you grow and operate the business

[00:30:08] - Apparel companies always being tied to identity

[00:31:03] - Analysis of Latch and learning about the relationship between hardware and software

[00:33:40] - How Latch works and why you might need it

[00:38:56] - Other businesses that may benefit from understanding the events that drive demand and using it as an opportunity for customer acquisition

[00:40:12] - The concept of density of demand and the power behind it

[00:41:33] - Other areas of operations density of demand could be applied 

[00:44:11] - Shared components that unite Avenir’s portfolio companies 

[00:46:14] - How he thinks about the world of private investment, having lived such a diverse career 

[00:50:22] - Developing relationships growing such a concentrated portfolio

[00:51:35] - Macro thoughts on the state of investing today

[00:52:59] - Defining and identifying characteristics of bad growth

[00:54:05] - The kindest thing anyone has ever done for him

My guest today is Alyssa Ravasio, co-founder and CEO of Hipcamp, a platform to discover and book your next camping trip. I was excited for this conversation as it combines two of my favorite passions – the outdoors and internet marketplaces. In our discussion, we cover how Alyssa bootstrapped demand in the early days of Hipcamp, the importance of creating not just great experiences but magical ones, and the evolution of Hipcamp’s business model. After listening to this episode, I’m sure the first thing you’ll want to do is get outside in nature. Please enjoy my conversation with Alyssa Ravasio.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.

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This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers.

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:57] - [First question] - The original insight that led to founding Hipcamp

[00:06:15] - What she studied in college and primary lessons learned there

[00:08:18] - Specific features of studying the internet that influenced her trajectory

[00:10:14] - Deciding what to attack first when developing Hipcamp’s infrastructure

[00:14:12] - Dimensions and market size of the outdoor industry

[00:15:48] - Organizing fragmented data into a useable schema and data set

[00:18:24] - What customers cared about most in the early days of Hipcamp

[00:20:00] - Managing focus and liquidity of the initial marketplace

[00:22:58] - Helping landowners manage the logistics of their property placements

[00:25:16] - Liability insurance in the outdoor industry

[00:27:35] - The biggest challenge faced in developing an outdoor marketplace

[00:30:03] - Amplifying and accelerating naturally grooved distribution

[00:32:32] - Identifying the top correlates of making magic happen

[00:34:55] - An ideal future for Hipcamp five years from now

[00:38:28] - What bad supply looks like and creating quality standards 

[00:42:08] - Their business model and revenue stream

[00:44:45] - Deciding on their take rate and the debate around booking fees

[00:46:14] - Lessons learned along the way as a leader

[00:47:42] - Unit economics from the host’s perspective

[00:52:33] - The most interesting businesses built on top of Hipcamp

[00:53:35] - Why is Hipcamp’s mission so important to her

[00:57:11] - The kindest thing anyone has ever done for her

My guest today is Josh Buckley. Josh is the new CEO of Product Hunt and an investor in many breakout companies like Rippling, Lattice, Boom Supersonic, and Relativity Space. In our conversation, we cover how video game companies are at the forefront of new business models, what current companies can learn from video game companies, Josh’s investing philosophy, and the three things he looks for when trying to identify the next legendary startup. Josh’s long experience operating his video game business, Mino Games, gives him such an interesting perspective as an investor, and I really enjoyed exploring that with him. Please enjoy my conversation with Josh Buckley.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:56] - [First question] - His start as an entrepreneur in online game

[00:05:09] - His parent's reaction to selling his first company at fifteen

[00:05:57] - Starting a second video game company 

[00:07:40] - The video game industry being ahead of the curve in performance marketing, distribution, and operations

[00:08:49] - Notable two year lag between gaming innovation and other consumer sectors

[00:10:50] - What is happening today in gaming that may be a glimpse into the future

[00:12:41] - Key elements for creating a great gaming experience

[00:15:29] - Building a meta game on top of the game itself to maximize engagement

[00:17:23] - Monetizing free to play games through in-game purchases

[00:20:25] - The most portable idea from fifteen years in gaming that can be applied to business

[00:22:02] - A future shift towards usage-based pricing models

[00:23:03] - His overall investment philosophy and strategy

[00:26:45] - Example of small a market with a high growth rate

[00:27:38] - Key elements of system elements and design when evaluating a business

[00:31:07] - What a flywheel looks like and investing in one such as Next Health 

[00:33:24] - Working core actions versus giving credit ones that aren’t yet working but may drive desirable outcomes

[00:34:13] - Why don’t more investing firms have a flywheel?

[00:39:04] - Product Hunt as a standalone business and part of a self-reinforcing ecosystem

[00:40:17] - Emerging systems and ecosystem edges in the digital landscape

[00:42:17] - Potential barriers for crypto becoming widely adopted in a variety of ways

[00:44:29] - New frontiers and platform shifts like crypto that may unlock new doors for companies

[00:45:13] - Which person has rewired his brain in his lifetime the most

[00:47:13] - Weirdness around Stripe and Plaid when he first encountered them

[00:48:37] - Meta games people in the industry are playing or should be playing

[00:51:25] - Controversial ideas around the business world today writ large 

[00:54:01] - Implications of shifting primarily towards a digital world

[00:54:14] - The kindest thing anyone has ever done for him

My guest today is Thomas Tull, the founder of Tulco LLC, an investment holding company that invests in businesses with high growth potential and helps them apply machine learning and data analytics. Thomas is also the founder and former CEO of Legendary Entertainment, the production company behind the Dark Knight, Hangover, Inception, 300, and many more iconic movies which he sold in 2016. In our discussion, we cover the movie industry’s value chain, the recipe for trying to make a successful movie and how Legendary pioneered the use of data analytics to improve those odds, and Thomas’ concept of the new physics of business and why it matters for what he’s now building at Tulco. Please enjoy my conversation with Thomas Tull.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:06] - [First question] - His overarching career philosophy and theme

[00:04:07] - Attacking a previously established industry in a new way

[00:05:20] - The origin story of Legendary and stepping into the film industry

[00:07:56] - Stakeholders involved in producing a movie and pre-existing profit pools when Legendary was founded

[00:12:44] - Topline and downstream revenue distribution of intellectual property from then versus now

[00:19:46] - Lessons learned about intellectual property writ large  

[00:19:03] - What makes Chris Nolan such an exceptional storyteller

[00:23:42] - Power and defensibility of cinematic universes and transmedia storytelling

[00:22:21] - Applying quantitative data analysis to film production and marketing

[00:25:55] - Competitive frontiers in movie studios and his advantageous skillset

[00:28:10] - Potential investment opportunities in media or media adjacent businesses

[00:29:26] - Interesting new tools that could be developed in entertainment technology

[00:31:00] - His favorite mind-blowing and awe-inspiring movies

[00:32:41] - Telling Jackie Robinson’s story in the film, 42

[00:35:30] - Jackie Robinson and Chadwick Boseman’s quiet dignity

[00:36:56] - Building the holding company Tulco 

[00:39:02] - The new physics of business that can’t be ignored

[00:42:40] - Modern velocity in the current era of business

[00:46:03] - Interweaving an antifragile mindset into the company culture

[00:47:55] - Who Tulco Labs is and what they do

[00:49:12] - What gets him most excited about exploring a new business for the first time

[00:50:48] - Unique characteristics he seeks out in a management team

[00:52:31] - Trends that make him feel worried about the future

[00:57:47] - Trends that make him feel optimistic about the future

[00:58:49] - An important lesson learned from his career on a personal level

[01:00:15] - The kindest thing anyone’s ever done for him

My guest today is Paul Enright, managing partner at Krainos Capital, his family office. Before running his own family office, Paul worked on the buy-side at Viking Global for over a decade managing their consumer and technology portfolios and before that at Morgan Stanley on the sell-side.

I thought Paul would be the perfect person to help me demystify the world of high finance – explaining the difference between the buy-side and sell-side, how long/shorts differ from long onlys, and walking through the various jobs in the investing world. In addition to setting that foundation, we also cover the evolution of the buy-side, what makes someone a great researcher verse a great stock picker, and various portfolio construction methodologies. Paul brings such a wealth of knowledge and experience to the table. I think this episode will be enjoyable for investing novices and professionals alike.

Please enjoy my conversation with Paul Enright.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:39] - [First question] - His history in both the buy and sell side

[00:05:20] - Different types of roles on the buy side and sell side

[00:06:48] - Interest sets that best align with being a buyer or a seller

[00:07:57] - The emotional experience of being on the buy side and exposed to risk

[00:08:53] - How the nature of buying and portfolio construction has changed 

[00:10;15] - What Regulation Fair Disclosure (Reg FD) is

[00:12:46] - Key terminology and definitions of long-only and long-short funds

[00:17:40] - Varying clusters of long-short funds and defining each type

[00:21:48] - Differences in exposure between a platform model versus a traditional long-short stock picking sense

[00:25:16] - Skill sets that are most important to have when navigating this space

[00:29:03] - What is good and what is great when it comes to “digging”

[00:31:20] - Why the quality of one’s analysis matters

[00:33:10] - Having a potential edge when deciding based on someone else’s analysis

[00:35:19] - Foundational building blocks of an effective pitch 

[00:37:20] - Finding wrongly identified stocks and reaping the rewards

[00:40:49] - Overview of good portfolio construction and lessons learned over the years

[00:44:06] - Why hedge funds tend to traffic heavily in T.M.T. and consumer sectors

[00:45:53] - Elements that strike him as great in a business

[00:48:05] - A business that once seemed great but has since faded away

[00:49:22] - Why hedge-fund managers seem to always make the most money

[00:53:50] - What a well run firm looks like

[00:56:39] - Characteristics that may make you well suited for a career in fund management

[01:00:23] - Why quality mentors and portfolio managers are so important when deciding where you want to work

[01:01:38] - What interests him mosts in markets today

[01:05:20] - Useful frameworks and formulas used when approaching a new business

[01:08:15] - Interesting features about telecom businesses and what defines them

[01:10:45] - The future of the modern world’s internet infrastructure

[01:14:44] - Abundance vs zero-sum and fixed vs growth mindsets 

[01:18:12] - The kindest thing anyone’s ever done for him

My guest today is Trevor McFedries, the founder of technology startup Brud and the creator of virtual pop star Miquela, a Gen Z icon with millions of fans worldwide. Trevor’s background is fascinating - he worked as a DJ and producer, toured with Katy Perry, worked at Spotify, and done just about every interesting thing I can imagine. In our conversation, we discuss the music-industrial complex, the creation of Miquela, and what Web 3.0 will mean for creators and builders in the future. I hope you enjoy this conversation with Trevor McFedries.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:54] - [First question] - What unites the diversity of his career

[00:03:39] - What inspired him to pivot away from football and step into creative arts

[00:05:50] - Lessons learned from being a touring DJ and producer that apply to the creative tech sector

[00:07:40] - A view of the music industrial complex from the inside

[00:08:57] - How the internet deciding who becomes popular affected already established artists

[00:10:57] - Interesting opportunities in the music landscape in 2021

[00:11:40] - Time spent at Spotify and the spark of insight that led to founding Brud

[00:16:02] - The sequence of creating a digital artist like Lil Miquela

[00:19:02] - What it feels like to be “othered”

[00:20:24] - Embracing one's intersections and applying it to a business model

[00:21:18] - The team behind Lil Miquela and her design process

[00:25:49] - Ingredients required for building a great narrative 

[00:28:35] - What social media platforms matter today, and the state of the social landscape

[00:32:21] - Expanding Lil Miquela’s world and digital media monetization

[00:36:32] - Differences between web 2.0 and 3.0 that may directly affect creators

[00:38:27] - Ways innovations like NFTs make spawn new network participants

[00:39:49] - Programmable art and media experiences

[00:41:03] - The most cutting-edge ideas in the digital persona space

[00:43:21] - Technology that wasn’t available that had to be built to enable new experiences 

[00:45:49] - One of the hardest decisions he’s had to make in Brud’s history

[00:47:16] - The furthest they’ve ever pushed the envelope

[00:48:06] - What’s the thing that keeps him going every day

[00:50:12] - Finding cultural white space and inventing a character that could speak to investing to inspire new generations

[00:52:01] - Units of media contribution and creative container experimentation

[00:53:27] - What has him the most excited about the future of his industry

[00:54:32] - Missing technological components that could inspire new digital creatives

[00:56:53] - Work ethic through the lens of developing a jump shot

[00:59:00] - One business lesson that he believes in deeply

[01:00:05] - The kindest thing anyone’s ever done for him

My guest today is Chris Dixon, a general partner at Andreessen Horowitz. Chris is a prolific investor and thinker, having been an entrepreneur, angel investor, and is now focused on investing in the crypto and blockchain space for Andreessen. Our conversation focuses on Chris's overall thesis for investing in the cryptocurrency space, the opportunities and limitations of blockchain applications, and why this is the most interesting area for investing and building over the next ten years. What's exciting to me is blockchain technology's ability to help us re-imagine old business models and catapult them into the 21st century – and we cover a lot of them. I hope you enjoy my conversation with Chris Dixon.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:56] - [First question] - His overall crypto investing philosophy

[00:06:37] - New opportunities presented by blockchain technology

[00:15:31] - Permanent limitations and shortcomings of blockchains

[00:18:32] - Evolution of DeFi and crypto currencies

[00:21:11] - Whitepapers: Bitcoin, Ethereum, MakerDAO 

[00:22:08] - How to take out a loan using the Maker protocol

[00:23:22] - Utility of Dai and stablecoins

[00:29:14] - How the DeFi network will reinvent the future

[00:39:53] - Uniswap, tokens, and fundamentally redefining leverage

[00:36:29] - The Company: A Short History of a Revolutionary Idea

[00:38:00] - Developer and entrepreneurial incentives for building blockchain technology

[00:39:46] - BitClout, Rally and the early days of social tokens

[00:46:38] - Demand curve and value creation efficiency in a digital creator economy

[00:47:24] - NFTs and a Thousand True Fans

[00:54:49] - Polkadot, Solana, Cosmos and programmable blockchains

[00:58:03] - The most exciting moment for him in the last year

[01:00:19] - Decentralized autonomous organizations

[01:02:46] - The single thing that has him most excited about the future of this space

[01:05:18] - The Next Big Thing Will Start Out Looking Like a Toy

Welcome to the first episode of our newest show, Business Breakdowns, featuring deep-dive conversations on individual businesses. In each episode, we will dissect a new company with investors and operators that know it best. 

We’ve already released the first three episodes on Shopify, Chipotle, and Alibaba. Subscribe to Business Breakdowns through the podcast player of your choice: 

• Apple
• Spotify
• Google
• Overcast
• Amazon

Leave us a 5-star rating on Apple Podcasts if you like the show!

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Today we will be diving into Shopify. Shopify was founded in 2004 by Tobi Lütke and Scott Lake around their original problem of why it's so hard to build an online business when they struggled to open an online snowboard equipment store. Today, Shopify's goal is to make commerce better for everyone, and it's used by more than 2 million merchants to run their online businesses. It's essentially an on-ramp for people looking to sell online. 

To help us break down Shopify, I'm joined by co-host Zack Fuss and our guest Alex Danco, who works on the Money team at Shopify.

To really understand Shopify, you have to understand its different business units -- Core, Merchant Services, Ecosystem, and the new Shop platform -- and the role they each play in making commerce easier and better for merchants. We begin this breakdown by covering each of those business units and how they compare to Apple's business lines. We then dive deep into how Shopify makes money through the first and second derivative of their merchant success and how Shopify thinks about friction in e-commerce. We close with an incredible analogy of Shopify and StarCraft and the tools that Shopify has built into the still-nascent world of e-commerce.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

Business Breakdowns is a property of Colossus, Inc. For more episodes of Business Breakdowns, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss

Show Notes

[00:04:03] - [First question] - What Shopify is as a product

[00:05:58] - Product pillar 1: Core[00:07:58] - Product pillar 2: Merchant services[00:10:02] - Product pillar 3: Ecosystem

[00:12:04] - Product pillar 4: Shop

[00:14:08] - The evolution of commerce with the rise of the internet

[00:21:01] - Differences between high and low trust commerce

[00:25:48] - The role of friction and trust in stakeholder variety

[00:30:18] - Overview of all four product pillars’ business models

[00:33:10] - Shopify App Store

[00:34:16] - How Shopify competes and partners with their competitors

[00:36:53] - Shop Pay expands to Facebook and Instagram

[00:38:49] - Key areas where Shopify will continue to grow across their product pillars

[00:42:52] - Affirm, Klarna, Afterpay

[00:43:56] - Potential pitfalls of having such a high self-imposed quality bar 

[00:45:12] - Conway’s law[00:45:12] - Aggregators versus platforms

[00:53:35] - Unique marketing aspects for Shopify’s sales and marketing with their subscription model 

[00:56:37] - Shopify: A StarCraft Inspired Business Strategy

My guest today is Tony Xu, co-founder, and CEO of DoorDash. Tony started DoorDash 7.5 years ago, and today it is one of the largest food delivery and logistics platforms globally, with operations in the US, Canada, Australia. In our conversation, we discuss the initial problem that DoorDash set out to solve, DoorDash’s counterintuitive approach to building their product, and the surprising benefits of capital constraints in DoorDash’s early days. DoorDash’s business model is an equal parts logistics nightmare and a human coordination problem, or as Tony puts it, a human and math problem. After talking to Tony, I feel his personality makes him a great candidate to solve those problems.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.

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This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device.

When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:07] - [First question] - The catalytic moment that inspired Tony to build DoorDash

[00:06:33] - Network density and its role in scalability

[00:09:15] - Solving a math and sales problem simultaneously

[00:11:33] - Becoming aware of multiple problem sets for restaurant owners

[00:14:34] - Designing a team to quantify friction and turn it into useable data

[00:16:49] - How to approach difficult problems and compartmentalize them in a practical way

[00:18:38] - Accounting for high-level variance in long-term goals

[00:21:54] - Factoring in time horizons for variance and planning for the future

[00:23:08] - Slowing down an action process to minimize a high-consequence decision

[00:26:48] - Generating demand after completing their software infrastructure

[00:28:15] - Strategic choices between network health and unit economics

[00:30:32] - Why DoorDash struggled to raise financing in their seed-stage

[00:32:23] - Solving a small fraction of a larger logistics problem

[00:35:00] - Differences between local commerce and distribution centers 

[00:36:44] - Creating the DashPass subscription service and how premium experiences influence user behavior

[00:38:34] - Advantages and potential diminishing returns in servant leadership

[00:40:41] - His broader philosophy on leadership and how it’s changed over the years

[00:44:55] - Creating an incentive-aligned culture of ownership at scale

[00:47:02] - The most surprising lessons learned about company building

[00:50:38] - Unexpected positive outcomes that may emerge in other areas due to DoorDash’s growth in the coming years 

[00:53:44] - Will DoorDash’s presence change behavioral patterns in where people choose to live or start their business?

[00:55:36] - What has him most excited for the future

[00:56:55] - Kindest thing anyone has ever done for him

My guests this week are Jesse Jacobs and Mike Kerns, co-founders and partners at The Chernin Group, TCG, a multi-stage investment firm dedicated to building consumer businesses. Many think of TCG as some of the best media investors in the world, and in this discussion, you’ll quickly see why. In our conversation, we cover how TCG identifies creators that they can help build businesses with, how established companies should think about influencers and media today, and what innovations they are most excited for in the creator space. As I become more heavily involved in building new media properties, Jesse and Mike are always my first point of call for advice, and I’m so excited to share this with you. Please enjoy my conversation with Jesse Jacobs and Mike Kerns.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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This episode is brought to you by MIT Investment Management Company – also known as MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo doesn’t care how small, new, or un-institutional your firm is if you have the potential to generate amazing results that support MIT’s pursuit of world-class education, cutting-edge research, and groundbreaking innovation.

Despite their willingness to invest early, they do not ask for GP economics, and they commit their initial capital for ten years.

Visit www.mitimco.org and their new emerging managers page to learn more.

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Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:32] - [First question] - The history of TCG 

[00:04:30] - iFilm (Discontinued)

[00:07:08] - Full Screen

[00:07:13] - Crunchyroll

[00:10:46] - Uniting properties across all of TCG’s brands[00:11:14] - Barstool, MeatEater[00:12:00] - Headspace, Food 52, Hodinkee, Surfline

[00:14:03] - Accidental businesses and pre-commercial success[00:14:53] - Exploding Kittens

[00:16:05] - Evaluating the potential of a new pitch

[00:19:12] - Testing, tracking and understanding media brand conversions

[00:21:13] - The most important things happening in media in 2021[00:25:12] - Analysis of MeatEater from content to commerce

[00:27:22] - First Lite

[00:29:21] - Replacing your own sponsors with owned companies

[00:30:11] - Analysis of Hodinkee from content to commerce

[00:33:42] - What sparked the resurgence of interest in collectibles

[00:38:05] - Hands on investing in the intersection of media, finance and tech 

[00:40:05] - Comcast 

[00:41:02] - Surprising discoveries in the sports collectibles space

[00:43:06] - NFTs and their role in generating capital for media companies

[00:44:25] - Sorare

[00:45:22] - JPG File Sells for $69 Million, as “NFT Mania” Gathers Pace

[00:47:23] - How to adapt to the NFT space as a business seeking equity

[00:51:12] - The valuation landscape of today

[00:55:25] - Defining success when working with an influencer

[00:58:48] - Upcoming trends they’re most excited about in the world

[01:01:40] - Roblox

[01:02:00] - Mr Beast, Beastburger

[01:02:47] - Pokemon Go

[01:04:01] - The kindest things anyone’s ever done for them

Welcome to Business Breakdowns, a new Colossus podcast featuring deep-dive conversations on individual businesses. In each episode, we will dissect a new company with investors and operators that know it best. We believe every business has secrets and lessons to learn from, and these conversations are designed to deliver that content in an entertaining and narrative format.

The series launches today with Shopify, so check out the links below and give it a listen. 

Subscribe to Business Breakdowns via: 

• Apple
• Spotify
• Google
• Overcast
• Amazon

Leave us a 5-star rating on Apple Podcasts if you like the show. 

With each new episode, we will be releasing full episode transcripts, show notes, and the best content we could find on that business from across the internet. Check out www.joincolossus.com for more. 

My guest today is Jesse Pujji, the Founder & CEO of Gateway X, a holding company that builds, buys, and invests in companies that are driving the direct-to-consumer landscape. Prior to Gateway X, Jesse was the CEO and co-founder of Ampush, a performance marketing business helping power customer acquisition across some of the world's biggest brands. Jesse is my go-to person for all things performance marketing and customer acquisition, so we decided to record this episode to bring his incredible lessons to a wider audience. It also dovetails nicely into the series of episodes we are making called Primers, where we take our audience from a 0 to a 7 on just about any topic. In this Primer with Jesse, we dive into how revenue mechanics affect ad campaigns, why long sales funnels often offer the greatest opportunities for differentiation, and the various channels and strategies available for performance marketing. I hope you enjoy my conversation with Jesse Pujji.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.

-----

This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device.

When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:58] - [First question] - Overview of Jesse’s career and starting Ampush

[00:12:11] - Red Ventures

[00:13:11] - The four components of performance marketing

[00:17:47] - Time and other variables in between impressions and revenue events

[00:23:12] - Understanding the dimensions of a business and their offering

[00:25:32] - Common misunderstandings businesses have about their marketing

[00:27:17] - Major changes in the Facebook and Google digital marketing ecosystems

[00:29:27] - Direct response marketing vs brand marketing[00:35:08] - The importance and impact of effective messaging

[00:37:28] - The differences between good and bad conversions

[00:40:56] - Does alpha still exist, is it worth looking for, and does beta have a place

[00:43:25] - Fundamentals of a high performing marketing organization

[00:50:04] - Attention aggregators of marketing agencies[00:50:18] - Nerdwallet - Thumbtack 

[00:51:22] - Product channel fit

[00:52:11] - PebblePost[00:53:58] - Lessons learned from working with Uber

[00:55:42] - Retention marketing [00:57:31] - Upcoming frontiers of performance marketing

[01:01:15] - Overview of Nerdwallet [01:03:36] - How Jesse’s time at Ampush has shaped his investment lens[01:07:20] - Lessons from bootstrapping a business vs venture capital funding

[01:17:05] - The entrepreneurial execution loop and operating cadence 

[01:29:20] - Kindest thing anyone has ever done for him

My guest today is Kanyi Maqubela, co-founder of seed-stage VC firm Kindred Ventures, which he started with his partner Steven Jang in 2019. Before founding Kindred Ventures, Kanyi was a general partner at Collaborative Fund. In our conversation, we discuss the parallels between today and the Roaring ’20s of the last century, the misunderstood risk curve of seed investing, and dive deep into how Kanyi evaluates founders and businesses at the earliest stage of company formation. We also discuss Kanyi’s experience teaching the Design Your Life class at Stanford and how some of those principles convinced him to take the leap to start his own fund. I hope you enjoy my conversation with Kanyi Maqubela.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:04:11] - [First question] - Understanding the roaring 20s and their potential resurgence

[00:06:14] - Seed-stage investing today compared to a few years ago

[00:09:02] - Lessons learned from studying the 1920s 

[00:11:52] - Supply chain infrastructure in the 21st century

[00:14:49] - His investment philosophy and what influenced it

[00:17:47] - Defining the risk curve and early-stage divergence

[00:21:31] - Assessing risk in seed-stage investing

[00:23:32] - Other moments that influenced Kanyi’s investment philosophy

[00:26:50] - Assisting early-stage companies as a VC 

[00:29:31] - How he approaches VC differently than traditional US VCs

[00:31:55] - Non-consensus ways and unique views when evaluating founders

[00:35:19] - Domain insight and its importance

[00:36:53] - What he looks for in a company when considering investing in them

[00:38:17] - Assessing a team in whether or not they have characteristics of longevity

[00:40:59] - Questions he most enjoys asking people

[00:42:24] - What makes for a good problem space

[00:44:26] - Early-stage crypto investing

[00:47:27] - How the crypto space and NFTs will change and influence other sectors

[00:50:37] - Emerging trends that are catching his attention

[00:54:20] - The potential for upward mobility in the coming decade

[00:56:30] - Teaching the Design Your Life course

[01:01:21] - Advice for modern investor-operators

[01:03:26] - If he could change one major thing in the industry

[01:06:57] - The biggest lesson learned from Obama’s campaign

[01:07:44] - The kindest thing anyone has ever done for him

My guest today is Roxanne Petraeus, co-founder and CEO of Ethena, a modern compliance platform for businesses. Roxanne’s background is pretty incredible, before starting Ethena she was a Rhodes Scholar, served in the US Army, and worked at McKinsey. In our conversation, we cover the lessons Roxanne ported over from her military career to building a business, how she’s trying to make compliance training not suck, and the woeful state of funding female founders in VC today and what can be done about it. Far from a boring conversation about compliance, this was an incredible discussion with one of the best founders I’ve met recently. I hope you enjoy my conversation with Roxanne Petraeus.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. 

See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial, check out klaviyo.com/founders. 

-----

This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers.

If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:29] - [First question] - What Ethena does

[00:06:31] - Lessons from her military career

[00:09:13] - Good and bad elements of leadership training from the military 

[00:11:35] - The problem of what sucks in compliance training

[00:14:33] - The enablement of bad behavior among people with power

[00:17:56] - The original idea for Ethena and bringing it to market

[00:21:15] - Determining who is the right person to serve first 

[00:24:03] - Lessons for building good software 

[00:26:21] - How they have adapted to working in and around regulation

[00:29:31] - Getting other companies to buy into the product

[00:34:45] - Creating effective content and measuring that effectiveness

[00:38:13] - Darker sides of growing the business and raising money

[00:39:57] -  How ‘the Motherhood Penalty’ Plays Out for Startup Founders

[00:43:12] - Fixing the problems with bias in venture capital investing

[00:46:57] - What is the outlook and long-term vision for the business

[00:50:38] - What has her most excited for the future

[00:51:53] - Most interesting about the Rhodes Scholar program

[00:54:02] - Kindest thing anyone has done for her

My guest today is Jesse Walden, the founder of Variant, an early-stage venture firm investing in crypto networks and platforms building the ownership economy.

With all the hype surrounding NFTs, I wanted to talk to Jesse about them, given his background in the music industry and his focus on the creator and ownership economy. The conversation did not disappoint. We discuss the basics of what an NFT is, what new creative paradigms they might unlock, and where we are in the NFT hype cycle.

This episode is the first in what will likely become its own show we are calling Primers. Our goal for primers is to bring investors and operators from a zero to a seven understanding of a topic, concept, or industry. The goal here is for the education around these topics to be fast and entertaining. I hope you enjoy this discussion with Jesse Walden and hopefully the first of many Primers to come.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:04:19] - [First question] - Simple definition of an NFT

[00:05:22] - What distinguishes NFTs from each other [00:06:24] - The value chain of a song, and who owns it

[00:12:07] - Monetization and royalties on traded tokens

[00:15:02] - Consumer incentives for purchasing NFTs

[00:19:19] - Long-term passive income and media legos

[00:22:23] - Technical breakdown of minting, hosting, and storing tokens

[00:24:28] - Verification of token ownership on the blockchain

[00:25:58] - NFT marketplaces and aggregators

[00:27:06] - Opensea.io 

[00:27:21] - Foundation.app 

[00:29:46] - Innovations inspired by the NFT explosion

[00:31:01] - Mirror.xyz 

[00:32:26] - NBA Topshot

[00:32:57] - Crypto Punks

[00:23:24] - Nifty Gateway

[00:34:30] - Physical cultural assets in the digital landscape

[00:36:02] - Legacy brands exploring digital goods and tokenized ownership

[00:38:37] - NFTs becoming the port of entry of all media [00:39:39] - An ownership economy in second generation internet platforms

[00:41:02] - Uniswap[00:42:41] - The “hype cycle” of NFTs and incoming market correction[00:44:18] - Lessons for investors in the NFT space

[00:45:15] - Lessons for buildings in the NFT space

[00:45:54] - Resources to continue learning about NFTs[00:45:54] - NFTs make the internet ownable by Jesse Walden[00:46:20] - NFTs and a thousand true fans by Chris Dixon[00:46:13] - A beginner’s guide to NFTs by Linda Xie

My guest today is Jonathan Goldberg, the founder, and CEO of Carbon Direct, a company focused on advising and investing in carbon removal at scale. Jonathan started his career in the commodities division of Goldman Sachs and then went on to start a commodity hedge fund, BBL Commodities. In our conversation, we cover the state of the carbon problem today, the importance of global carbon standards and carbon taxes, and the future of carbon capture and removal technologies. This was a masterclass on all things carbon-related. Please enjoy my conversation with Jonathan Goldberg. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. 

See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial, check out klaviyo.com/founders. 

-----

This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers.

If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders.

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:25] - [First question] - Overview of his career

[00:06:02] - The start of his commodities trading strategy and its evolution 

[00:09:08] - Key strategies for making money as a commodities trader

[00:10:41] - Opportunity to trade commodities today 

[00:11:39] - Making the shift to carbon capture work

[00:15:04] - Range of consequences for elevated carbon emissions and biggest buckets of carbon

[00:18:52] - An outline of the Paris Climate Accord and other agreements on climate change

[00:20:26] - Ways to remove carbon from the atmosphere

[00:23:46] - The technology to remove carbon and incentives to invest in this technology

[00:26:19] - Corporate participation in the carbon trade 

[00:28:35] - Balance of natural vs man-made solutions 

[00:31:53] - Making money without the altruistic goals

[00:33:43] - Trends in the fossil fuel industry 

[00:36:41] - Convenient ways for consumers to switch to clean energy products

[00:39:57] - The geopolitical will to shift towards cleaner energy

[00:41:58] - Primary consequences of not making this shift

[00:44:25] - The important role of regulation 

[00:46:01] - Thinking through the investing side of combating climate change

[00:48:59] - Kindest thing anyone has done for him

My guest this week is Marissa King, a professor of organizational behavior at the Yale School of Management. I was fascinated by Marissa's work after coming across her book, Social Chemistry: Decoding the Elements of Human Connection, earlier this year. Our conversation covers the three types of social networking styles, the surprising impact of COVID on social networks, and what her research tells us about building high-performing teams. This episode covers many topics I haven't explored before that I find fascinating. I hope you enjoy my conversation with Marissa King.   

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:04:04] - [First question] - Origin of her career and topics she is focused on

[00:04:06] - Social Chemistry: Decoding the Patterns of Human Connection

[00:04:09] - Priya Parker Podcast Episode

[00:05:41] - Why the focus on Autism and some of the trends around it

[00:08:07] - Prevalence of mental health and substance abuse vs. raised awareness

[00:09:16] - The eureka moment for her in this research

[00:10:16] - Pattern in growing large social movements

[00:11:43] - The Expansionists group and their role in large social movements

[00:14:31] - Acid test for the Brokers group

[00:15:35] - How she developed the categories of people that drive social movements

[00:17:35] - Most memorable moments of discovery in the development of these categories

[00:18:58] - Important categories for overall network science

[00:20:20] - Behavioral changes we can make to improve the nature of our social connections

[00:23:21] - The pitfalls for each group and how they can invest in their own network

[00:25:29] - Conveners and what they need to improve 

[00:26:34] - Downside of being a broker

[00:27:58] - The attachments styles of secure, anxious, or avoidant

[00:30:07] - Velocity of interactions possible today and what it means for research

[00:32:02] - How men and women develop networks differently

[00:33:55] - What is unique in organizational behavior through the lens of her research

[00:36:19] - Best practice for creating high output interactions

[00:37:33] - Putting together the perfect team

[00:38:42] - Largest pitfalls in putting together a good team

[00:40:00] - Role of conversation in effective network building

[00:41:15] - Being a great listeners and distractions

[00:42:47] - Eric Maddox Podcast Episode

[00:43:41] - Good policy for running a network, being attentive to the network

[00:46:40] - The power of touch

[00:48:39] - How movements become societal and what role technology has played

[00:52:46] - How this applies to a business

[00:53:34] - Biological underpinnings of Dunbar’s number

[00:57:13] - Kindest thing anyone has done for her

My guest this week is Jonathan Neman, the co-founder and CEO of Sweetgreen. Sweetgreen is a fast-casual restaurant chain that Jonathan co-founded in 2007 during their senior year at Georgetown when he realized they couldn't find a healthy, affordable, and convenient place to eat. Today, Sweetgreen operates in 11 markets and will have about 160 restaurants across the US by the end of 2021. In our conversation, we cover the origins of Sweetgreen and how it builds a direct relationship with its customers, how Jonathan thinks restaurants should work with marketplaces like DoorDash, and the economics of operating restaurants. While Sweetgreen is primarily a restaurant concept, Jonathan brings a tech-first mindset to the food industry, focusing less on single-store economics and more about customer lifetime value and the importance of owning the relationship with the customer. I hope you enjoy my conversation with Jonathan Neman.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. 

See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial, check out klaviyo.com/founders. 

-----

This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device. 

When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply. 

-----

Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:04] - [First question] - The origins of Sweetgreen

[00:05:47] - Something they did from a position of naivete, working their supply chain

[00:07:18] - Most common reason restaurants go wrong

[00:08:35] - Building the first restaurant and lessons along the way 

[00:12:22] - Effective menu building

[00:14:36] - The Sweetgreen network and how they view the restaurant as a network

[00:21:05] - What their digital business means compared to other restaurant businesses

[00:23:55] - How they have improved at converting people into their ecosystem

[00:27:40] - Creating win-win partnerships

[00:29:12] - The pros/cons of the marketplaces in the food industry

[00:32:58] - The general economics of a restaurant

[00:36:58] - Allocating capital differently when the focus is the customer and not the store

[00:39:36] - How tech trends aimed at improving personal health plays into Sweetgreen’s plans

[00:45:11] - Their focus on sustainability for the business

[00:47:56] - The core values of ‘Add the Sweet Touch’ and ‘Live the Sweet Life’

[00:50:18] - Kindest thing anyone has done for him

[00:51:38] - Never Eat Alone: And Other Secrets to Success, One Relationship at a Time

My guests today are Josh Wolfe and Tony Thomas, better known as T2. Josh is the co-founder and General Partner at Lux Capital. T2 is now a venture partner alongside Josh at Lux Capital, after serving for almost 40 years in the US military and becoming a 4-star general and the 11th Commander of US Special Operations Command. Our conversation focuses on the technology frontier in defense as well as the geopolitical threats that the US faces. We talk about everything from semiconductors and autonomous weapons systems to the moral dimensions of investing in defense technology. I hope you enjoy this fascinating conversation with Josh Wolfe and Tony Thomas.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

------

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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This episode is brought to you by MIT Investment Management Company – also known as MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo doesn’t care how small, new, or un-institutional your firm is if you have the potential to generate amazing results that support MIT’s pursuit of world-class education, cutting-edge research, and groundbreaking innovation.

Despite their willingness to invest early, they do not ask for GP economics and they commit their initial capital for ten years.  

Visit www.mitimco.org and their new emerging managers page to learn more.

------

Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:46] - [First question] - Overview of Tony Thomas’s career

[00:06:36] - His focus on the information wars and truthiness

[00:08:50] - How Josh and Tony met

[00:12:27] - Experiencing the slow pace of technology growth within the Department of Defense

[00:15:51] - History of businesses selling to and engaging with the government

[00:23:52] - Consensus of the threats we face today 

[00:28:55] - Most important competitive frontier today 

[00:35:09] - The lessening of kinetic warfare

[00:46:51] - State of the drone technology and industry 

[00:52:56] - Mapping the arctic and the geopolitical ramifications

[00:54:31] - The frontier of space 

[00:59:26] - What shouldn’t be unmanned technology 

[01:02:31] - The cutting edge of simulation technology 

[01:06:50] - The most important thing to know about the future of semiconductors

[01:11:36] - The moral lens of working with and investing in defense companies

[01:20:53] - Traits of the most exceptional soldiers he’s served with

[01:23:53] - Kindest thing anyone has done for Tony

My guest today is Matteo Franceschetti, the founder and CEO of Eight Sleep, a smart mattress company. I’m a customer of Eight Sleep and this was one of the most unique founder conversations I’ve had on the show, in both the focus on the product and the exploration of sleep. We talk about which biometrics matter, how hard it is to start a hardware company and launch manufacturing overseas, how Matteo manages his own sleep, and the massive potential for preventative health companies like Eight Sleep may have in the future. I hope you enjoy this conversation with Matteo Franceschetti. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:36] - [First question] - Origins of the Eight Sleep business

[00:03:21] - Designing and testing the original product

[00:04:17] - Goal of the product

[00:05:19] - How temperature can improve sleep

[00:06:28] - Accuracy of the sensors in this product

[00:08:30] - Valuable inputs for health that they measure, HRV (heart rate variability)

[00:09:59] - Amount of research on the variables they measure and impact on health

[00:11:45] - Hardest data for them to measure in their mattress

[00:14:03] - Early challenges to launching the business

[00:15:27] - Lessons from the early manufacturing process

[00:16:50] - Working through the potential business models

[00:17:56] - Goal of less sleep and reducing light sleep

[00:19:45] - Behavior changes he’s made as a result of understanding his sleep more

[00:21:08] - How alcohol/caffeine impacts sleep

[00:22:01] - How food impacts sleep

[00:23:01] - Why glucose spikes are bad for sleep

[00:23:40] - Challenges in the business after the crowdfunding stage

[00:25:34] - Marketing lessons from a high price point and infrequently purchased product

[00:26:42] - Most exciting day in the researching phase

[00:27:48] - Turning an infrequent purchase into a frequent sale

[00:28:54] - What it’s like to work with his wife

[00:30:03] - Future of the quantified self-movement

[00:31:23] - The hardest challenge in the business

[00:32:13] - Most valuable things he’s learned as a fan of Formula 1 racing

[00:33:41] - Future of the mattress business

[00:35:28] - Other businesses he has learned from

[00:36:40] - Lessons from the data part of the business

[00:38:26] - Collecting more data from their customers without being intrusive

[00:39:56] - What he’s learned through Apple Health 

[00:41:39] - What has him excited for the long term future of Eight Sleep

[00:42:32] - Kindest thing anyone has done for him

My guest today is Jack Clark, head coach of the University of California Varsity Rugby team. Jack has one of the highest winning percentages not only at the collegiate level but in sports history, winning an incredible 90% of games since his start as a coach in 1984. That includes a 98 game winning streak from 1990 to 1996 and a 115 game winning streak from 2004 to 2009. In our conversation, we dive into how Jack builds high-performing teams, the shared vocabulary he creates across his organization, and his work with companies applying what he's learned on the field to operating businesses. Please enjoy this conversation with Jack Clark. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

------

This episode is brought to you by MIT Investment Management Company. MITIMCO is the endowment office of MIT. New and small investment funds listen up. MITIMCO is looking to find investors starting funds today.

MITIMCO is partnership-driven, long-term focused, and has an extensive history of backing investors early in their careers. These partners are key in delivering the outstanding investment returns required to support MIT's pursuit of world-class education, cutting-edge research, and groundbreaking innovation. MITIMCO is focused on finding and partnering with the best investors across the globe, no matter the market environment. No firm is too small, too young, or too non-institutional.

If you or someone you know is currently in the process of starting a fund or recently launched, please email partner@mitimco.org or discover more on their website at mitimco.org/partner.

------

Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:44] - [First question] - Overview of his playing and coaching career

[00:06:02] - The importance of creating a set of values for a team

[00:07:53] - Why selflessness is such an important trait he looks for in teams

[00:09:20] - Examples of selflessness in the teams

[00:10:06] - The Winner Within: A Life Plan for Team Players

[00:10:24] - Lessons on gratitude and entitlement

[00:11:34] - Being a meritocracy on the team

[00:12:55] - Rewarding merit as a coach

[00:14:18] - Improving a team today, the power of the basics and fundamentals

[00:15:29] - Defining toughness for players and teams

[00:17:29] - Mark Bingham, the epitome of toughness

[00:18:33] - Why he created and how he uses a glossary

[00:22:09] - Creating a high rate of conversion in recruiting

[00:25:01] - What qualities did the teams that beat him share

[00:27:22] - Take on pride and something he is exceedingly proud of

[00:29:17] - Translating the concepts from the court into the business world

[00:32:20] - Where companies have room to improve

[00:33:16] - Changing a company culture

[00:34:21] - Coaches he has learned from 

[00:36:00] - The power of non-cognitive grit

[00:38:45] - Advice for companies creating a value set

[00:40:40] - Kindest thing anyone has done for him 

My guest today is Ryan Petersen, founder and CEO of Flexport. Flexport is a technology platform for global trade. In this conversation, Ryan takes us through the fragmented world of international freight shipping, and we dive deep into the history and inefficiencies of the system. We also cover how shipping containers were standardized, how new protocols get adopted internationally, and the challenges of doing business in the “no man's land” of international waters. Ryan is the type of entrepreneur I enjoy talking to most: he has incredible domain knowledge, high energy and is tackling an enormous global problem. I hope you enjoy my conversation with Ryan Petersen.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies, on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders.

-----

Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:24] - [First question] - Overview of what Flexport does

[00:04:49] - His introduction into the world of shipping

[00:06:49] - Difference between parcel and freight

[00:08:53] - Market cap of the overall shipping industry

[00:12:52] - Worst parts of the shipping world

[00:15:34] - Improving the tech behind the shipping container

[00:19:06] - Why the shipping container changed the world

[00:19:07] - The Box: How the Shipping Container Made the World Smaller and the World Economy Bigger

[00:21:27] - Teams and outsider perspectives in solving problems

[00:22:34] - How their business could make shipping more efficient and reduce costs

[00:25:24] - Where the margins and profits are made in shipping

[00:25:49] - Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger

[00:27:11] - The finance side of shipping

[00:28:56] - Maritime law and the ocean

[00:30:57] - How much is left in the digitization of shipping

[00:32:48] - The perfect state of shipping using Flexport

[00:38:19] - Investing in hard assets to expand the business

[00:41:03] - Lessons about building a business and global coordination

[00:43:15] - Multidisciplinary thinking among their team

[00:44:04] - Global supply chain issues in light of Covid and ocean policing 

[00:44:15] - Peter Zeihan Podcast Episode

[00:47:59] - Testing out demand in the beginning

[00:50:28] - The process of testing out new ideas and killing off losers

[00:52:33] - Important lessons/themes for founders

[00:54:51] - Hardest learned lesson, fundraising

[00:58:06] - Other opportunities in shipping

[00:59:47] - Lessons for creating a new standard

[01:02:22] - Using their standardization to improve global relief work

[01:04:40] - Creating synchronicity in a company

[01:07:09] - What he’s excited about for the future

[01:07:53] - Kindest thing anyone has done for him

My guest today is Jeremy Grantham. Jeremy is the Long-Term Investment Strategist and Co-Founder at GMO. Jeremy has an encyclopedic knowledge of the history of markets, which made it such a pleasure to have him back on the show. In this conversation, we discuss the three key signs of a bubble, why Jeremy believes we are in a bubble right now and how it’s being led by retail rather than institutional investors. We close with the important role that demographics and productivity will play over the next few decades across the world. Please enjoy my conversation with Jeremy Grantham.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Koyfin, one of the fastest-growing fintech startups. I discovered Koyfin earlier this year when I asked Twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com. 

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This episode is brought to you by MIT Investment Management Company. MITIMCO is the endowment office of MIT. New and small investment funds listen up. MITIMCO is looking to find investors starting funds today.

MITIMCO is partnership-driven, long-term focused, and has an extensive history of backing investors early in their careers. These partners are key in delivering the outstanding investment returns required to support MIT's pursuit of world-class education, cutting-edge research, and groundbreaking innovation. MITIMCO is focused on finding and partnering with the best investors across the globe, no matter the market environment. No firm is too small, too young, or too non-institutional.

If you or someone you know is currently in the process of starting a fund or recently launched, please email partner@mitimco.org or discover more on their website at mitimco.org/partner.

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Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:03] - [First question] - His view on the markets today 

[00:03:07] - Jeremy Grantham’s Podcast Episode

[00:08:00] - Proliferation of SPAC’s and how he views them as a potential bubble

[00:10:20] - Could SPAC’s help to improve the IPO process

[00:14:30] - How he viewed the Gamestop story through his historical context 

[00:18:24] - Is investor education possible 

[00:19:50] - How the increasing role of retail investors impacts bubbles

[00:24:15] - Attitudes towards market bears in bubbles

[00:28:52] - Long term view on the economy and the forces pushing it higher

[00:41:50] - Returning to a hard money standard for the US economy

[00:49:39] - Would a finite supply of money change market trajectory

[00:51:02] - Best ways to improve the infrastructure of the economy and people’s willingness to work

[00:53:52] - What should one do if they believe we are in a bubble

[00:58:14] - What he is excited about in his green investments

[01:02:28] - Advice to young investors  

My guest today is Carlos Brito, CEO of Anheuser-Busch InBev. AB InBev is the world’s largest brewer of beer and maintains a portfolio of hundreds of beer brands across the globe. Our conversation focuses on AB InBev’s culture of ownership, how Carlos balances organic growth with acquisitions and managing disruption as an industry incumbent. I loved hearing about Carlos’ story from growing up in Brazil to now running one of the largest businesses in the world. I hope you enjoy my conversation with Carlos Brito.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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This episode is brought to you by NetSuite. NetSuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly.Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at netsuite.com/invest.

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Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:12] - [First question] - His career path and how he got to where he is today

[00:11:02] - Culture building lessons throughout his career

[00:14:52] - Maintaining ownership of company culture as businesses grow 

[00:16:47] - How and why they avoid wasted resources

[00:18:49] - Why conserving resources is so beneficial for a company

[00:21:18] - Spreading culture into new members of a team

[00:25:26] - Lessons from managing a large portfolio of different brands

[00:27:58] - Biggest mistakes he has seen within brands

[00:29:38] - Navigating changes/threats in the beer industry, starting with craft beers

[00:32:56] - Lessons from the production and distribution side of the business 

[00:36:02] - How to assess and decide to move into a new market

[00:37:12] - Role of data in deciding how to allocate resources and capital

[00:40:34] - The evolution of marketing over his career

[00:44:32] - Implementing the meritocracy to keep the right people in the company and move them around

[00:47:59] - Feedback he needed to hear

[00:49:16] - How other leaders can decide on whether to focus on inorganic or organic growth

[00:51:41] - What he’s most proud of from his career

[00:53:13] - Passion for the product

[00:54:12] - Most memorable beer in his life

[00:54:56] - Kindest thing anyone has done for him

My guest today is Scott Belsky. Scott was the co-founder and CEO of Behance, the world's largest creative network, and a prolific angel investor, having made early-stage investments in Pinterest, Uber, Carta, and Airtable. His company was acquired by Adobe in 2012, where he is currently the chief product officer. In this conversation, we cover the importance of focusing on the first mile of a customer's experience with your product, why every user is (at first) either lazy, vain or selfish, and what the rise of creativity tools means for creators and investors in the future. We also cover the major trends that Scott thinks will dominate for the next decade. This was one of those conversations where I was left with 10 great lessons that will stick with me for a long time. Please enjoy my conversation with Scott Belsky.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:24] - [First question] - Philosophy for building great products

[00:04:52] - Starting the journey of building a great product 

[00:06:08] - Making the first mile better

[00:08:12] - Understanding user progress in product building 

[00:10:25] - Getting to awareness and attention and interest in a product 

[00:12:41] - The concept of window dressing

[00:14:24] - Taking an idea and turning it into a high-value product 

[00:14:42] - The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture and Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality

[00:16:49] - Keeping rewards structure in place for teams to stay engaged

[00:19:56] - Using his knowledge in product building to invest in other companies

[00:24:00] - The concept of object model

[00:25:52] - User psychology concepts they keep in mind when designing a product

[00:27:51] - Implementing all of these strategies into a product

[00:29:25] - The era of eduployment

[00:31:05] - How this will impact colleges

[00:33:27] - The evolution of the talent/audience relationship

[00:35:32] - Decentralization and the companies of 1

[00:37:44] - How that decentralization will impact his investment thesis

[00:39:21] - How increased productivity tools could help with more creativity in the workplace

[00:42:04] - Training people to be more creative in the workplace

[00:44:33] - Future of user interfaces

[00:44:58] - The Interface Layer: Where Design Commoditizes Tech

[00:48:10] - Good design principles

[00:49:51] - The future coming out of Covid

[00:52:09] - Kindest thing anyone has done for him

My guest today is Matt Mullenweg, co-founder and CEO of Automattic, the company on top of the open-source project WordPress that Matt helped start. Today, WordPress powers 40% of all the websites in the world. Our wide-ranging conversation covers the state of the internet when Matt first started WordPress, the symbiotic relationship between open source and proprietary projects, and how the most successful companies are really master world builders. I hope you enjoy this great conversation with Matt Mullenweg.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.

With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. 

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Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:15] – [First question] – What the internet felt like when he first started building Wordpress

[00:05:11] – What was wrong with his impression of the internet then

[00:06:50] – Being a connoisseur of things overlooked 

[00:08:34] – How permission less publishing and open source software shaped the internet

[00:12:30] – Balance between centralization and decentralization and where we are in the cycle

[00:14:08] – The cycle between direct-to-consumer and having intermediary

[00:16:32] – New opportunities and challenges of the internet today

[00:18:49] – Potential of cryptocurrency to enable big changes on the internet

[00:21:22] – The idea of distributed work via the internet and the utopia of it

[00:21:38] - Sam Harris podcast with Matt Mullenweg

[00:24:31] – Advantage of having a team distributed across geographies and timezones

[00:26:46] – What he learned from the Amazon’s API mandate

[00:29:12] – Landmines of distributed work

[00:31:13] – Interesting lessons learned building Wordpress

[00:34:55] – Company building as world building

[00:35:52] – Lessons from Microsoft on platform building

[00:38:53] – Key ingredient to world building within your company

[00:41:09] – Lessons from Wix and Shopify 

[00:42:23] – How to decide what to do next in resource and capital allocation

[00:47:00] – How to engage with other stakeholders in a platform business

[00:50:06] – The continued connectivity created by the internet

[00:53:14] – Kindest thing anyone has done for him