Invest Like the Best with Patrick O'Shaughnessy

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Minh
 Aug 15, 2018
Densed, high speed, high quality knowledge. Thanks Patrick, for this.

Description

Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com

Episode Date
Julio Vasconcellos & Mate Pencz - Investing in Latin America - [Invest Like the Best, EP.296]
01:01:30

My guests today are Julio Vasconcellos and Mate Pencz, who are partners at Canary and Atlantico, leading early-stage investment firms in Latin America. They’re also both successful entrepreneurs. Mate is the co-founder and CEO of Brazilian real estate unicorn, Loft. Julio was Facebook’s first country lead for Brazil, an entrepreneur in residence at Benchmark, and the former founder of Peixe Urbano which sold to Baidu. This conversation was a great opportunity to dive into the state of investing and business in Latin America today, what it looks like on the ground, and cover the most interesting findings from Atlantico's annual report on Digital Transformation in the region. Please enjoy my conversation with Julio and Mate.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:39] - [First question] - A broad perspective on what is interesting in Latin American investing today - Latin America Digital Report 2022

[00:05:15] - What makes up the existing 1.5% tech penetration index in Lat Am

[00:06:11] - Florian Hagenbuch, Mate Pencz - Everything Will be Bought Online (Loft); David Velez - Building the Branchless Network (Nubank); How important it is to parse by country when it comes to building businesses in LatAm 

[00:08:31] - Overview of LatAm as a microcosm of fintech innovation happening really fast and what is most exciting in that sphere 

[00:12:28] - Why the adoption of PIX was so successful and how it maps onto the banking system

[00:14:27] - What PIX’s widespread adoption will enable for the coming wave of entrepreneurs 

[00:18:30] - Demographics, GDP, growth rates, and inequality in LatAm

[00:22:30] - Shifting to remote work and how it’ll affect LatAm workers and talent

[00:25:25] - Macro tailwinds that matter when it comes to returns in these markes

[00:30:06] - What it feels like for an entrepreneur today compared to when Loft launched 

[00:32:36] - Deeper themes and what needs to be unlocked for LatAm’s tech sector to look more like the US or China with big tech giants 

[00:37:04] - The opportunity set in developing a software that serves small and medium businesses in LatAm

[00:40:12] - Sources of available funding for venture and private equity  

[00:42:54] - What valuations look like and whether or not there’s an entry multiple discount

[00:45:12] - Seeking evidence that crypto is used in more valuable ways in emerging markets 

[00:48:00] - Areas where LatAm is operating in a future state more so than elsewhere

[00:50:28] - What the right amount of global firm participation in capital partnerships looks like

[00:52:38] - Big standout lessons from their operating days 

[00:55:53] - What is most exciting and concerning about their investing style and investing writ large in LatAm 

[00:58:51] - The kindest thing anyone has ever done for Julio

Sep 27, 2022
Trina Spear - Billion Dollar Scrubs - [Invest Like the Best, EP.295]
49:13

My guest today is Trina Spear, a former investor at Blackstone and the co-founder and CEO of FIGS. FIGS is a multi-billion-dollar public company that built a category-leading brand selling scrubs to healthcare professionals. It was a problem hiding in plain sight and FIGS solved it through vertical integration and customer obsession. Trina shares so many interesting, simple lessons that are often ignored in business. Please enjoy my great conversation with Trina Spear.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:28] - [First question] - The original insight that lead to founding FIGS

[00:04:28] - Why obvious opportunities can go so long before being seized 

[00:06:23] - Key dimensions needed to improve the product and the early days 

[00:09:02] - Basic overview of a clothing retailer’s financial profile

[00:10:49] - Financing the business and the early stage cash flow cycle 

[00:13:04] - Strategies to manage workflow and making sacrifices

[00:14:43] - Advice for people trying to build their brands in a hands-on way 

[00:17:14] - The biggest calculated risk she took in the first five years

[00:19:00] - Building a foundation that allowed for such explosive growth

[00:21:44] - The story that allowed FIGS to connect with their customers

[00:24:43] - Painting a picture of the size and scope of healthcare apparel

[00:26:22] - Things lazy companies do and thoughts on product variety

[00:28:54] - Defining SKU productivity and what to do with low productivity products 

[00:30:21] - Chip Wilson Book; Lessons learned from reading Chip’s story

[00:31:58] - Balancing a healthy relationship with your CFO

[00:33:59] - Where she sees the most runway to tackle and continue to execute

[00:35:46] - A women-lead industry and her time spent with Meg Whitman

[00:38:13] - The most essential jobs she feels she has and shouldn’t do as the CEO

[00:40:03] - Thoughts about relationships with investors and messaging 

[00:42:14] - What she’d be most focus on in founders if she was just an investor 

[00:43:57] - The most stressful thing that has ever come across her desk 

[00:44:41] - What types of things bring her the most joy in building FIGS

[00:45:27] - Philosophy of hiring given their small team and when it’s okay to hire

[00:46:56] - Whether or not there’s a role for non A players in businesses

[00:47:48] - The kindest thing anyone has ever done for her

Sep 20, 2022
Gabriel Leydon - How Web3 Onboards a Billion Users - [Web3 Breakdowns, EP.37]
59:25

Today, we are sharing an episode of Web3 Breakdowns with you. My Invest Like the Best conversation with Gabe Leydon last year was one of my favorites and became one of our most popular. Since that conversation, Gabe has become one of the most interesting builders in web3 that I know so I was excited to have him back to share his views of the space and how it might grow. If you enjoy this episode, subscribe to Web3 Breakdowns on your preferred podcast player.

 

My guest today is Gabe Leydon, who’s episode last year was one of our most popular ever. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I know. He was the co-founder of Machine Zone, which pioneered free-to-play hits like Mobile Strike and Game of War. Over the past year, he has been in stealth mode building a web2 meets web3 video game company called Limit Break, which is founded on a brand new business model that he calls free-to-own. We dive into his vision for the future of gaming, how it could onboard a billion users onto the Ethereum network, and why the LTVs of crypto gamers are so far higher than their web2 counterparts. Please enjoy this conversation with Gabe Leydon.

 

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 Coinbase Prime. Coinbase Prime combines advanced trading, battle-tested custody, financing, and prime services in a single solution. Clients have used our comprehensive investing platform to execute some of the largest trades in the industry because they are the only publicly-traded company with experience trading and custodying crypto assets at scale. Get started with Coinbase Prime today at coinbase.com/prime.

 

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Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 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: @Web3Breakdowns | @ericgoldenx | @patrick_oshag 

 

Show Notes

[00:02:19] - [First question] - What free-to-own gaming means and why it’s exciting 

[00:11:40] - Pre-existing behavior that sets up free-to-own for success

[00:12:32] - The progression from PFP NFTs to clubs and the road ahead

[00:14:16] - Overview of the business and monetization model for free-to-own games

[00:17:51] - The story of DigiDaigaku, their mechanics, the drops, and what lead to their creation

[00:22:14] - Balancing supply and demand in a free-to-own market

[00:24:35] - Creativity and extensions of the DigiDaigaku NFTs

[00:26:13] - Tiering, breeding and the role the Genesis series will play in the Digi universe

[00:27:32] - The level of brand marketing NFTs will unlock for businesses

[00:29:57] - How free-to-own will be the primary monetization method for brands

[00:31:21] - A future with a global marketing shift towards digital property and economies

[00:33:06] - Why most of the winning PFP projects are of unique characters

[00:35:50] - His Twitter strategy and how he’s created such a fervor around him

[00:42:40] - What will define the legendary marketers over the coming decade 

[00:43:06] - Interoperability needed to make real-world NFT uses appealing to consumers 

[00:44:44] - Whether or not we’ll see more token-gated business in the future 

[00:45:40] - Stable Diffusion and his impression of the new AI art generating bots

[00:48:56] - What great distribution looks like in a digitally native world

[00:50:03] - The emphasis of innovation taking place in the metaverse being a bad thing

[00:53:24] - Things he most admires in adjacent games and creators in his world

[00:54:25] - Unique game mechanics that Web3 technology unlocks 

[00:56:16] - NFTs will be the gateway for people to acquire crypto

Sep 15, 2022
Harley Finkelstein - Building the Entrepreneurship Company - [Invest Like the Best, EP.294]
01:05:45

My guest today is Harley Finkelstein. Harley is the President of Shopify and has been with the company since its early years. He is a lawyer by training but an entrepreneur by calling and that is the focus of our discussion. We discuss the different dimensions of entrepreneurship and Shopify’s role in promoting it, as well as exploring the company’s transition to public markets, and what the last few years have been like. Please enjoy my discussion with Harley Finkelstein. 

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:26] - [First question] - His interpretation and definition of a person’s life's work 

[00:05:50] - The story of the riverstone and the average polished executive 

[00:08:36] - The thing he can’t help but do; and focusing on our compulsions

[00:13:12] - How he would boil things down to the most simple entrepreneurial formula; Distilled

[00:16:38] - What is harder and easier about new business formation today 

[00:21:03] - The countervailing forces for small-to-medium business entrepreneurship 

[00:24:31] - What he’s learned about operationalizing ideas and mentor lessons

[00:29:08] - A piece of fortune cookie advice that he finds terrible

[00:30:49] - How Brands Grow; his philosophy on marketing & distribution  

[00:35:27] - The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses

[00:38:43] - What it was like getting their first app developer for the Shopify app store

[00:41:17] - The state of ecommerce today writ large and what trends are interesting 

[00:45:46] - Lessons learned about the digital places that people are buying 

[00:49:06] - What it’s been like as an executive working at a company that had their stock price explode over the pandemic 

[00:52:25] - Tips for communicating effectively with Wall Street

[00:54:14] - An investor that stands out in memory that really impressed him

[00:55:10] - Important aspects of his world that are worth mentioning 

[00:57:04] - Lessons learned about motivating people through DJing 

[00:59:12] - Whether or not reading the crowd can apply to business

[01:03:49] - The kindest thing anyone has ever done for him

Sep 13, 2022
Mitch Lasky - The Business of Gaming - [Invest Like the Best, EP.293]
01:13:24

My guest today is Mitch Lasky. Mitch is a partner at Benchmark and one of the leading figures in the video game industry. Over the last 30 years, he has built, led, and invested in a number of the best gaming companies in the world, including Activision, EA, Riot, Snapchat, and Discord. I couldn’t think of a better person to break down the anatomy of great gaming businesses and Mitch does not disappoint. His insights are remarkable. Please enjoy this excellent conversation with Mitch Lasky.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:31] - [First question] - Why there aren’t more famous gaming investors

[00:05:08] - The most important features of the modern gaming business model

[00:07:11] - Developing his aesthetic taste and investing decision skill

[00:08:03] - What makes a game fun 

[00:09:26] - How delivering a pleasurable active user experience differs from passive content and media

[00:11:09] - The developers of Doom being the first real modern video game company

[00:13:09] - Half-Life’s important role in the development of the gaming industry

[00:14:50] - The powerful notion of the platform-based publisher model

[00:17:54] - How some of the big game aggregators get started in the first place

[00:19:58] - What Riot can teach non-gaming businesses about business writ large

[00:21:10] - Ways that the change from physical games to downloads changed monetization

[00:25:19] - How to quantify an economic model in the new paradigm of superfan monetization

[00:28:27] - What the shift in gaming platforms has done to the business model

[00:31:47] - The impact of Apple’s privacy changes on gaming revenue

[00:34:11] - How the access to professional game engines and a lower friction environment will change the industry

[00:37:04] - Whether or not there is a step beyond mobile

[00:39:42] - Ways platforms like Twitch and Discord have influenced gaming

[00:42:26] - What he’s learned about games that allow them to seemingly exist forever

[00:45:17] - Signs of a healthy gaming community

[00:46:21] - The role of celebrities and influencers and generating retained audiences

[00:47:45] - Whether or not crypto will unlock new opportunities for in-game monetization 

[00:52:50] - Key categories of motivators that could replace a ponzi-style in-game inflation 

[00:54:36] - Contrasting League of Legends versus a Ready Player One style world

[00:58:22] - Emerging technologies and trends that may revolutionize the industry 

[01:00:29] - A future with further consolidation on distribution and power

[01:02:41] - The most genius game pattern he’s ever played

[01:04:44] - What attributes will define the great game investors in the coming decades

[01:06:59] - How much his experience lends itself to investing in other sectors

[01:11:07] - The kindest thing anyone has ever done for him

Sep 06, 2022
David Senra - Passion & Pain - [Invest Like the Best, EP.292]
01:22:57

My guest today is David Senra. David has studied history’s great founders and entrepreneurs in more depth than anyone I’ve ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. I found this to be one of the most energizing conversations I’ve had in a long time, and one I’ll return to often.

 

David’s work and extraordinary energy aligns so well with our mission at Colossus that we’re excited to partner with him. You’ll soon be able to find his podcasts and transcripts at joincolossus.com where we hope you’ll learn as much from him as we have. If you like this conversation, be sure to subscribe to David’s podcast called Founders. Now onto our discussion. Please enjoy this great conversation with David Senra.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:01] - [First question] - When he first fell in love with reading

[00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast

[00:10:34] - The first time he connected with someone as a positive role model that he was reading about 

[00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies 

[00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives

[00:22:45] - The dynamic and relationship between inspiration and perspiration 

[00:27:11] - Commonalities between the layers of leadership and support underneath founders

[00:31:52] - Where else he’s seen ego rear its head in good and bad ways 

[00:38:34] - How often do great founders break the law or enter gray areas of it 

[00:41:22] - The role constant learning and listening plays in success

[00:45:12] - Talking about how anything worth doing is worth doing to excess 

[00:52:18] - Describing the soul of founders and businesses

[00:58:39] - What he’s learned about all of these founders as it relates to marketing 

[01:04:38] - A common story that process is often art 

[01:08:10] - Who his idols are in podcasting specifically 

[01:14:55] - Major aspects of people he’s studied that haven’t been discussed yet

[01:19:55] - The kindest thing anyone has ever done for him

Aug 30, 2022
Robert Smith - Investing in Enterprise Software - [Invest Like the Best, EP.291]
56:34

My guest today is Robert Smith, the founder, Chairman, and CEO of Vista Equity Partners. An engineer by training, Robert started Vista at the turn of the millennium and built it into one of the world's most successful software-focused investment firms. We discuss the white space left in enterprise software investing, the importance of capital cycles, and what he’s learned building an iconic investing franchise. Please enjoy my discussion with Robert Smith.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:34] - [First question] - What the enterprise software market looks and feels like to him

[00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades

[00:09:42] - Bringing an engineering mindset to enterprise software investing and culture

[00:12:36] - A single change he made to a business that stands out most in memory

[00:14:33] - Qualities that are most critical in defining a good enterprise software company

[00:18:07] - How the profile of companies he’s bought has changed over the years

[00:20:33] - Categories of software he tends to gravitate towards 

[00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples 

[00:27:17] - Lessons learned about customer churn over his twenty two year career

[00:29:44] - Capital cycles and how much they truly impact the software world 

[00:31:53] - What elements of building Vista have most appealed to him over the years  

[00:34:31] - Changing their investment strategy as the world continues to change

[00:38:06] - The war for talent and what his senior team would debate most 

[00:40:01] - Biggest mistakes Vista has made and what they taught him

[00:41:09] - What has him most insecure or paranoid about the platform he’s built

[00:43:10] - The advice he’d give on having good relationships with LPs

[00:44:57] - The largest risk he or Vista has ever intentionally taken 

[00:46:15] - What he’s learned about having a winning negotiations and sales approach

[00:49:27] - Who he’d give all of his capital to outside of Vista

[00:50:06] - How he arrived at the themes he tends to be philanthropic towards

[00:53:08] - The work he does in the foster world

[00:54:49] - The kindest thing anyone has ever done for him

Aug 23, 2022
Katherine Boyle - Investing for America - [Invest Like the Best, EP.290]
54:46

My guest today is Katherine Boyle, a general partner at Andreessen Horowitz. Katherine started her career as a reporter for The Washington Post before moving into VC at General Catalyst. She now leads a practice at a16z called American Dynamism, investing in companies that are solving critical issues in areas like defense, housing, and education. In the past year, I've spoken to Marc Andreessen, Josh Wolfe, and a number of founders about this need to build societally important businesses so I was excited to explore the topic in even more detail today. Please enjoy my conversation with Katherine Boyle.

 

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

 

The content here is for informational purposes only and should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security and is not directed at any investors or potential investors in any a16z fund. For more details, please see a16z.com/disclosures.

 

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:42] - [First question] - The origin and overview of the term American Dynamism 

[00:05:01] - Why the shift to a move slow and make sure nothing breaks mentality

[00:07:31] - What about the American system today feels broken and stale 

[00:09:48] - Becoming a journalist at The Washington Post 

[00:11:35] - Describing the power landscape of media as it exists today  

[00:12:28] - Major categories of American Dynamism that matter most  

[00:14:29] - What matters more or less to her as an investor in  these categories 

[00:17:31] - Whether or not there’s anything fundamentally broken about our government

[00:19:36] - The Systems Bible; What excites her about aerospace and defense and what creates opportunity and demand in these sectors

[00:22:44] - Explanation of what it means when the factory is the product 

[00:23:47] - How much is flowing into aerospace and defense currently 

[00:26:01] - An overview of how lobbying works and who does it and why

[00:29:07] - Whether or not she considers these sectors from a bottom up perspective as in investor   

[00:30:32] - What other categories she feels pulled towards 

[00:33:09] - The biggest problems that currently exist in the K-12 school system 

[00:35:34] - Thoughts on how states are competing citizens and how it plays into American Dynamism

[00:37:34] - The role immigration will play in range of outcomes in these main categories 

[00:39:32] - Key takeaways about housing in light of American Dynamism  

[00:42:09] - Her interpretation of the chart that shows inflation in categories over time

[00:44:40] - How different the investing dynamics are in all of these categories and thoughts on valuation in this world 

[00:47:56] - Whether or not expected returns and risk profiles are different in this area 

[00:48:36] - The importance of effective a founder’s storytelling, knowledge and customer empathy

[00:49:55] - Overview of the anatomy of a great story  

[00:51:30] - The story she tells founders at this stage so establish a partnership 

[00:52:46] - The kindest thing that anyone has ever done for her

Aug 16, 2022
Ravi Gupta - Focus - [Invest Like the Best, EP.289]
01:17:15

My guest today is Ravi Gupta. Ravi spent a decade in private equity at KKR before joining Instacart as their first CFO and COO. He navigated them through a critical moment in their history and returned to investing in 2019 as a partner at Sequoia. Our discussion gets to the heart of what it means to build and invest in great businesses, and we talk a lot about the personal side of the journey, which tends to get overlooked. Please enjoy this great conversation with Ravi Gupta.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

-----

 

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:34] - [First question] - Why it’s important to keep the main thing the main thing

[00:04:59] - His first exposure to this idea; How Will You Measure Your Life

[00:07:50] - Thoughts on the conflict of the main thing for a business and a person

[00:11:45] - The most painful episode of enacting this philosophy at Instacart 

[00:16:13] - How this concept has manifested in his life as an investor at Sequoia 

[00:19:16] - Amazon’s 14 leadership principles vs. his concept of focus

[00:21:55] - What good main things share in common and their attributes; Frank Slootman Episode

[00:24:48] - Whether or not the feedback loop for things that work are very short 

[00:26:04] - The nature of joy and competitiveness in company culture 

[00:29:01] - How he assesses the depth that motivation runs through people and companies

[00:32:43] - Analysis of his own motivations in life 

[00:35:34] - Differences and shortcomings of virtuous and vicious motivators 

[00:37:15] - How to accurately figure out someones motivators in a short period of time

[00:40:22] - Being Demanding and Supportive; Why these words pair so well together

[00:45:55] - What he’s looking for in companies given all of the ideas discussed so far

[00:51:11] - How his ideology manifests inside of Sequoia 

[00:58:44] - What it’s like to mentor an apprentice and how to do it well

[01:02:40] - Adjusting behaviors to meet current markets where they’re at 

[01:06:13] - Defining what a great product is

[01:07:56] - What he did to turn around Instacart by narrowing their focus

[01:12:28] - The things that most drove the switchover at Instacart

[01:14:53] - The kindest thing anyone has ever done for him

Aug 09, 2022
Will Thorndike - The Power of Long Holding Periods - [Invest Like the Best, EP.288]
59:00

My guest today is Will Thorndike. I first spoke to Will in 2017 about his excellent book The Outsiders and his career in private equity. I titled that conversation: How Skilled Capital Allocators Compound Capital. In many ways this conversation continues where that one left off. Through the lens of his new project, a podcast called 50X, we explore the power of multi-decade holding periods and the shared characteristics of businesses that are able to compound returns at high rates for abnormally long periods of time. Please enjoy this discussion with my friend, Will Thorndike, and if you haven’t subscribed to 50X, I highly recommend doing so.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

-----

 

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

Invest Like the Best is a property of Colossus, LLC. 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

[00:02:45] - [First question] - How working on The Outsiders project shaped his thinking

[00:06:29] - His interest in long-term holding periods and dealing with multi-decade time horizons

[00:09:42] - Shared characteristics among compounding machines

[00:11:23] - Defining capital efficiency and the return on tangible capital metric 

[00:13:02] - An example of an attractive business that requires a lot maintenance CapEx

[00:14:22] - Thoughts on the measurement of intangibles and whether or not he’d avoid great businesses that are intangible heavy 

[00:15:25] - Tangible ways capital efficiency rolls into compounding capacity 

[00:17:45] - Being patient early on and things that reveal themselves after doing thorough year long research in a company like TransDigm

[00:20:32] - Lessons learned about good game selection for companies 

[00:22:47] - Common features of customers that tend to be served by the businesses he invests in 

[00:23:43] - Evaluating culture and its ability to propagate forward in the public equity markets 

[00:25:09] - An example of a decentralized structure and why it works so well

[00:27:53] - Successful decentralized companies regularly assemble general managers and compare their results and share ideas

[00:28:46] - Thoughts about software as a business model and lessons learned about this industry across his career

[00:30:00] - What the best serial acquirers do for long-term holders

[00:31:46] - Advantages of using debt for financing and acquisitions  

[00:33:39] - How different the future might be for young CEOs with capital allocator mindsets

[00:35:40] - Other forms of recurring revenue he’s seen and things that are one the line between recurring and non-recurring revenue

[00:37:42] - The biggest changes for him moving from outside client capital to just managing his own

[00:39:09] - 3 companies that Housatonic Partners has owned for more than 25 years

[00:40:29] - What made Karen Moriarty so good for so long 

[00:42:36] - The crossover between public and private investing and the virtues of each sector

[00:45:35] - How he thinks about the function of Compounding Labs and what he wants it to become 

[00:47:10] - What is at the top of his wish list of the companies he wants to explore 

[00:49:15] - Which companies he’d still be fascinated to learn about that don’t fit the criteria he’s laid out today 

[00:50:25] - The development of investor conviction over time and what he’s learned about it

[00:52:19] - Lessons learned about producing great media

[00:53:43] - What he can teach us about deep research on companies with analysts

[00:55:10] - Adjusting his thinking and investing in a high variance world

Aug 02, 2022
Alok Vasudev - Searching for White Space - [Invest Like the Best, EP.287]
01:11:42

My guest today is Alok Vasudev. Alok is an early-stage investor who has been in the crypto space for a very long time. Before co-founding Standard Crypto, he was an investor at Benchmark and S28 Capital. Given Alok's experience and the prevailing mood right now in crypto, this is a particularly interesting discussion on the ecosystem writ large. We discuss whether the bubble can be thought of as productive speculation, his views on skeptics in the space, and look at some big, potentially, underestimated ideas. Please enjoy my conversation with Alok Vasudev.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

-----

 

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:31] - [First question] - His history in venture and thoughts on the crypto ecosystem

[00:06:06] - What it means to be great at searching for white space as a venture capitalist

[00:08:00] - Things his original venture peers would say he was best and worst at

[00:09:24] - How he would address crypto skeptics broadly given today’s market

[00:13:35] - Whether or not it’s appropriate to look at each crypto token as a stock 

[00:15:32] - The pool of demand for Dai and the end use-case itself for the stablecoin 

[00:17:01] - What matters to him the most in the world of stablecoins 

[00:19:59] - Defining sound and unsound collateral 

[00:21:02] - Why the US doesn’t digitize the dollar and how being a government entity would impede some of their capabilities 

[00:23:21] - What a community operated computer unlocks compared to a standalone one

[00:27:09] - What persistence and resilience from community computers open up  

[00:29:30] - Something going on that people aren’t talking about yet in regards to blockchains

[00:33:54] - The notion of productive speculation and what it means 

[00:36:03] - One of the best historical examples of productive speculation

[00:42:29] - How things outside of the blockchain become integrated and connected to it

[00:45:43] - Ways crypto will impact the gaming world over the coming years

[00:49:10] - Handicapping a potential future where NFTs work and blockchains don’t benefit

[00:51:42] - Thoughts on the world of art, IP, NFTs, and its changing landscape

[00:54:43] - Whether or not there are companies being built that can streamline and facilitate this form of connection between artists and their fanbases

[00:58:13] - Other controversial opinions he holds in the crypto community 

[01:03:13] - What he’s most bullish and bearish on right now

[01:07:29] - The kindest thing anyone has ever done for him

Jul 26, 2022
Matthew Ball - A Manual to The Metaverse - [Invest Like the Best, EP.286]
01:20:14

My guest today is Matthew Ball. Matt is an investor, the former head of strategy at Amazon studios, and one of the brightest minds in the media industry. Through his essays and now his book, which launches today, Matt has established himself as the foremost authority on the Metaverse, which has stormed into the public eye since I first had him on the show two years ago. The Metaverse is the focus of our discussion and I hope you enjoy this encyclopedic tour through all of its details as much as I did.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:37] - [First question] - Which most represents the Metaverse: Minecraft, Ready Player One, Fortnite, or Facebook’s Horizon

[00:05:58] - Facebook trying to own the concept of the Metaverse by changing their name 

[00:09:22] - Defining what the Metaverse is and a good working definition of it

[00:11:33] - The state of the engines behind 3D output and the history of them 

[00:16:32] - The role IP played in bootstrapping the first Metaverses 

[00:18:32] - Where the ability to create digital environments will lead, and what Unreal 7 could look like compared to Unreal 5 today

[00:21:03] - Natural limits of the Metaverse compared to real-world experiences

[00:24:16] - Other sensory inputs that will need to be improved for digital immersion

[00:26:59] - Why the initial excitement of trying something like Oculus wears off over time, both for casual gamers and those excited about this new frontier

[00:31:40] - Changes in technology and new projects that have him most excited that will empower the digital infrastructure for Metaverses

[00:37:14] - What interoperability means and why it has its own chapter in his book

[00:31:52] - How Roblox connects with Fortnite and how far down we need to go to build a bridge between digital worlds

[00:46:13] - What will drive commerce in the Metaverse and the possibility for a singular currency standard

[00:51:35] - Considering the demand for the Metaverse and whether or not it will be a constraint on adoption and success

[00:57:37] - What the modern equivalent of a lemonade stand will be in the Metaverse

[00:59:58] - The lower adoption rates for more participatory media consumption
[01:03:19] - Potential pitfalls and the dark side of the metaverse

[01:06:14] - Who the categorical winners of the Metaverse might be   

[01:14:15] - The top things he would suggest exploring to best understand the Metaverse

Jul 19, 2022
TransDigm: Foundations with Nick Howley [50X, EP.1]
01:24:18

Today we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of 50X – a new series from Will Thorndike and the team at Compounding Labs, in partnership with ColossusWill’s book, The Outsiders, is one of the best business and investing books you will find. Now you will hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold.

First up is TransDigm, an aerospace components manufacturer that has returned over 1,750X since its inception nearly three decades earlier. In this episode, Will is joined by Nick Howley, TransDigm’s long-time CEO and Chairman. Make sure to subscribe to 50X in 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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This episode is brought to you by Tegus. The team at Tegus has built a full company intelligence platform aimed at streamlining the investment research process. In preparation for the 50X series, we actively used Tegus to gain qualitative insights beyond traditional reported data. To learn more and enjoy a free trial, visit tegus.co/50x

 

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50X is a podcast that dissects the anatomy of extraordinary long-term investments. The show is hosted by Will Thorndike and the team at Compounding Labs, and brought to you in partnership with Colossus.

 

In each episode of 50X, we look in detail at an investment that has appreciated at least 50-fold. From the seat of the professional investor and occasionally the CEO, we explore its origins, evolution, and eventual outcome, studying key themes around long-term value creation ranging from operations, capital allocation, and culture to pivotal buy and sell decisions. To enhance the quality and depth of our interviews, we rigorously study each asset in advance, diving into all available public and private resources.

 

Learn more and dive into our research at 50xpodcast.com

 

Follow us on Twitter: @50Xpodcast and @joincolossus

 

Show Notes

[00:00:00] – 50X Introduction 

[00:02:00] – Sponsorship: Tegus

[00:07:04] – Episode Introduction 

[00:09:05] – Nick’s Background pre-TransDigm

[00:11:56] – Original Acquisition from Imo Industries in 1993

[00:15:33] – Thesis and Performance under Kelso & Co.’s Ownership

[00:18:42] – Genesis of Three Key Value Drivers: Price, Productivity, and New Business

[00:21:07] – Building the Management Team

[00:24:05] – Early Lessons on Value Drivers

[00:27:53] – Capital Allocation under Kelso & Co.

[00:28:51] – Sale to Odyssey Investment Partners in 1998

[00:30:26] – Strategy under Odyssey’s Ownership

[00:31:51] – Early Acquisitions and Integration Playbook

[00:37:26] – Early External Crises

[00:41:13] – Snapshot at Conclusion of Odyssey’s Ownership in 2003

[00:43:19] – Building a Decentralized Culture  

[00:46:23] – Differentiated Approach to Compensation

[00:52:12] – Sale to Warburg Pincus in 2003

[00:55:51] – Shift to Inorganic Growth under Warburg’s Ownership

[00:58:08] – Evolution of M&A Process

[01:05:37] – Post-Acquisition Expectations and Post-Mortem Process

[01:09:48] – Divesting Acquired Assets to Maintain Focus

[01:11:29] – Embedding Value-Generative Culture via Hiring and Training

[01:13:54] – Quarterly Product Line Reviews

[01:20:43] – Recap of Private Investment Returns and Snapshot pre-IPO

Jul 14, 2022
Alice Bentinck - Building a Start-Up Machine - [Invest Like the Best, EP.285]
01:03:41

My guest today is Alice Bentinck, co-founder of Entrepreneur First. Entrepreneur First, or EF, invests pre-company by systematizing the way that talented individuals find co-founders, develop ideas, and scale into companies. They’re an incubator of teams and ideas on a mission to create impactful companies that, without their help, wouldn’t exist. I first spoke with Alice’s co-founder, Matt Clifford, over two years ago and have been fascinated with EF’s model of investing ever since. Please enjoy my conversation with Alice Bentinck.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:33] - [First question] - Overview of what Entrepreneur First is today

[00:05:57] - How she identifies the people to bring into each cohort and convince them to quit their job to join EF for eight weeks

[00:10:10] - Categories of the main types of people who join the EF program

[00:12:32] - What she’s learned about negative screening at the first stage of recruits 

[00:14:07] - Positive signals she looks for in early admissions 

[00:17:46] - What the program itself feels like as a participant

[00:21:29] - Reasons partners tend to fail and whether or not EF advises equity splits between founders

[00:24:49] - How important the idea is that the team will be working on 

[00:28:04] - Exercises she enjoys doing with the new cohorts around social norms

[00:30:38] - How the experience looks physically in each city 

[00:32:57] - Categories of data collected as the cohorts unfold and making investment decisions

[00:36:46] - Ways the companies mature after EF and what kinds of investors fund the next stage of their startups

[00:40:55] - Why aren’t there ten EF style initiatives or organizations

[00:44:26] - Motivations for the change in their holding company structure

[00:46:48] - The love of product and ideas she’s playing with right now

[00:51:49] - Cities she has her eye on that EF is not a participant in today and criteria that makes a city desirable for EF

[00:54:03] - A piece of software that EF could benefit from that doesn’t exist yet

[00:55:30] - The keys to her harmonious relationship with her co-founder Matt 

[00:59:01] - National and international impediments that directly impact company building

[01:01:36] - The kindest thing anyone has ever done for her

Jul 12, 2022
Jess Lee - Designing Investment Products - [Invest Like the Best, EP.284]
58:05

My guest today is Jess Lee. Jess is a partner at Sequoia Capital as well as their Chief Product Officer. Before becoming an investor, Jess co-founded fashion app, Polyvore, and was an early product manager for Google Maps. Most recently, she founded All Raise, a non-profit that is changing the gender balance in tech. Our discussion ranges from Burning Man to Marvel to Sequoia’s mobile app and I hope that Jess’s passion for delighting users rubs off on you. Please enjoy my conversation with Jess Lee.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:35] - [First question] - Why more investment firms don’t have a product mindset

[00:05:22] - How to approach building a productized version of capital 

[00:08:00] - Ways Ampersand measures success and judging their own performance 

[00:08:49] - Driving reasons that Sequoia wins deals beyond their brand name

[00:10:28] - How her work as CPO at Sequoia has changed her investing approach

[00:12:28] - Everything she’s learned about community and its relevance to business 

[00:17:48] - What the gold standards are for studying strongly built communities 

[00:19:42] - What it is about Comic-Con that works so well from a community standard  

[00:21:18] - The role that scarcity plays in communities writ large

[00:23:10] - Product mindset and customer obsession 

[00:24:33] - Knowing when it’s okay to begin expanding 

[00:25:14] - The formative experiences or lenses that inform her investing decisions

[00:28:12] - Rates of change in her investment progress and dollars going to female founders

[00:29:36] - Systemic bias and what’s driving a lack of funds towards female founders 

[00:32:26] - How she applies community building lessons to All Raise

[00:33:20] - The internal learning culture in Sequoia that others could adopt and benefit from

[00:37:01] - Which Marvel superheroes her Sequoia partners would be  

[00:39:05] - Seeds of motivation for Arc and what it is

[00:43:06] - When you should innovate and when you shouldn’t reinvent the wheel 

[00:44:31] - The best ways she’s seen companies manage and support human capital

[00:45:36] - Biggest mistakes made when managing human capital 

[00:46:42] - What working on Google Maps taught her about product development 

[00:48:42] - Someone she admires and has learned the most from in All Raise  

[00:50:02] - Measuring success at Sequoia over the next ten years  

[00:52:20] - The kindest thing anyone has ever done for her

[00:53:42] - What it was that made the people who believed in her take a chance on her 

[00:55:03] - Things in pop culture today that most has her attention

Jul 05, 2022
Kenneth Stanley - Greatness Without Goals - [Invest Like the Best, EP.283]
01:13:50

My guest today is Ken Stanley. Ken is a Professor in Computer Science and a pioneer in the field of neuroevolution. He is also the co-author of a book called, Why Greatness Cannot Be Planned, which details a provocative idea that setting big, audacious goals can reduce the odds of achieving something great. We discuss that revelation in detail and how to apply it in our day-to-day lives. Please enjoy this great discussion with Ken Stanley.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

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Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - The best way to change the world is to stop trying to change it

[00:06:26] - The kinds of goals his work addresses and the ones it doesn’t

[00:08:46] - Almost no prerequisite to any major invention was invented with that major invention in mind

[00:14:04] - Picbreeder

[00:17:21] - How looking for specific results often makes arriving at them a longer process

[00:24:00] - The importance of the individual in a web of invention and disruption

[00:28:30] - How generations progressed in Picbreeder when consensus mechanisms were inserted into the process 

[00:31:24] - Examples of stepping stones that were invented that became something even greater

[00:36:02] - What his research means for how we should conduct ourselves writ large

[00:44:17] - Thoughts on necessity being the mother of all invention

[00:50:08] - The ways that society is arranged is psychologically toxic

[00:55:14] - The role that constraints play in creative output and outcomes in general; Brett Victor - Inventing on Principle

[01:01:10] - What the constraints are that he sets for himself in AI development

[01:04:44] - To know what’s new you need to know what’s not new

[01:06:47] - The kindest thing anyone has ever done for him

[01:08:28] - How he would allocate resources to create more innovation in the world

Jun 28, 2022
Lydia Jett - Investing in E-commerce - [Invest Like the Best, EP.282]
01:07:44

My guest today is Lydia Jett, Managing Partner of SoftBank Investment Advisers. Lydia leads the team’s consumer, internet, and e-commerce investments and has worked with many of the most significant consumer platforms in the world, including as a board member of Coupang and Flipkart. We cover all aspects of e-commerce and explore Lydia’s evolution as an investor alongside Masa Son at SoftBank. Please enjoy my conversation with Lydia Jett. 

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

-----

 

Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:34] - [First question] - What curiosity thread she’s been pulling on thus far in her career

[00:05:17] - The biggest felt differences doing things one way for a decade and changing now

[00:07:08] - Learning about tailwinds and what the predominant ones are that exist today

[00:08:38] - How much room to go there is left in the world transitioning to e-commerce

[00:10:44] - Competitive frontiers that exist today in e-commerce

[00:12:14] - What drives companies that grow faster than their competitors

[00:13:15] - What areas the world’s most innovative e-commerce companies are focused on

[00:16:38] - Unique characteristics that they select for in ecommerce CEOs and founders

[00:17:44] - Which country she would send an American investor to in order to learn more

[00:19:03] - Upside down approaches to e-commerce that aren’t common in America yet

[00:20:15] - Subcategories and sub sectors she’s most drawn towards lately

[00:23:05] - Lessons learned about business models that don’t work in e-commerce

[00:27:47] - What western investors should know about Coupang 

[00:30:12] - Everything she’s learned about vertical integration

[00:33:01] - Everything she’s learned and cares about in regards to margins

[00:34:24] - Evaluating a younger company’s ability to drive margins in the future

[00:37:17] - The most extreme version of efficiency gain she’s seen deployed

[00:39:06] - Whether or not the public perception of SoftBank’s simplified approach is accurate

[00:41:27] - The role the size of assets plays at SoftBank

[00:47:42] - Focusing on efficiency and smart allocation first before trying to scale 

[00:50:33] - Companies as products that investors buy and defining what great looks like

[00:53:16] - The danger of premature optimization around a set of KPIs 

[00:55:46] - How important the specific founder is for their given e-commerce company

[00:58:18] - Why e-commerce companies tend to start from a worse place than offline ones

[00:59:45] - Ways that she’s changed from working alongside Masayoshi Son for a year

[01:03:31] - Who comes most to mind as a great investor    

[01:05:23] - The kindest thing that anyone has ever done for her

Jun 21, 2022
Josh Wolfe & Chris Power - Factories of the Future - [Invest Like the Best, EP.281]
01:09:22

My guests today are Josh Wolfe and Chris Power. Josh will be a familiar voice to many of you and is the co-founder and General Partner of Lux Capital. Chris is the founder and CEO of advanced manufacturing start-up, Hadrian. Most of our discussion centers on the need to modernize the factories that supply our space and defense industries. But given the current market environment, we also talk about capital conditions and the responsibility to build products that really matter. Please enjoy this conversation with Josh Wolfe and Chris Power.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

-----

 

Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:40] - [First question] - An overview of the precision manufacturing industry writ large

[00:08:28] - Why the manufacturing sector has so many great investment opportunities

[00:12:58] - Anduril Breakdown; What Hadrian in its final form will unlock for manufacturing

[00:16:08] - What the demand side looks like for manufacturers in its current state today 

[00:18:29] - How the nature of demand will shift for this style of manufacturing in the future

[00:22:51] - Important rare earth materials, supply chain constraints, and the revival of commodities 

[00:27:55] - The key set of jobs being done by mom and pop shops that could be innovated on and done within a Hadrian factory 

[00:30:35] - What is going on inside of a Hadrian factory and how they will evolve over time 

[00:32:10] - Prosecuting diligence on someone's ability to execute on their behalf

[00:37:14] - The PhD arrogance trap and how a Hadrian machine will be better in five years from now

[00:39:44] - Units of innovation and optimization driven by software 

[00:41:43] - Walkthrough of the bubble and anti-bubble concept and funding companies in today’s markets  

[00:48:08] - Breadth of ability versus focus and selling parts to buyers early on

[00:50:42] - Lessons learned and advice for understanding the focus problem 

[00:52:32] - Whether or not the climbing costs of experimentation is a bad thing

[00:56:39] - Fat startup vs. lean startups and making the hardest irreversible decision during Hadrian’s early days

[00:58:31] - Enduring more schlep work than less being a good signal

[00:59:06] - Chris’ thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes

[01:03:36] - Josh’s thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes

[01:07:22] - The kindest thing anyone has ever done for Chris

Jun 14, 2022
Martin Casado - The Past, Present, and Future of Digital Infrastructure - [Invest Like the Best, EP.280]
54:10

My guest today is Martin Casado. Martin is a general partner at Andreessen Horowitz where he focuses on digital infrastructure. Before joining a16z, Martin pioneered software-defined networking and co-founded Nicira, which was bought by VMware for $1.3 billion in 2012. Martin has studied, built, and invested in digital infrastructure his whole career and is the perfect person to discuss the most interesting aspects of the industry. Please enjoy this great conversation with Martin Casado.

 

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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

-----

 

Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:43] - [First question] - The state of the digital infrastructure industry today 

[00:04:02] - The major stages and eras of cloud technology 

[00:06:30] - Overview of Dropbox’s story and the two major trends at the time of its emergence

[00:10:12] - Lost margin and lost market cap from big users of the public cloud 

[00:12:14] - Whether or not there is a headwind coming for public cloud providers

[00:14:07] - The base level primitives of the digital world and innovation within those areas

[00:17:33] - How entrepreneurs might go after the biggest public cloud providers

[00:19:37] - His view on API first companies and granular monetizable units in growing markets

[00:23:20] - Developer facing tools and what works well when going to market 

[00:25:34] - Lessons learned about successfully building relationships between a company and developers as a buying class 

[00:27:12] - The difference between a front-end and back-end developer and what is changing in their responsibilities 

[00:28:45] - What he looks for as an investor when he’s processing a new API first company

[00:30:31] - Common redflags and disqualifying observations for an API first company 

[00:31:59] - Pricing usage and building a revenue model around one of these businesses

[00:33:49] - Reasons why this proliferation is happening and important parts of the data stack

[00:36:35] - Frank Slootman Episode; Snowflake’s offering for their users, their explosive growth, and primitives in their sector

[00:39:06] - The history of digital security and potential opportunities as an investor

[00:40:19] - How digital infrastructure intersects with the real world and hardware world

[00:42:14] - What he’s most excited about that digital infrastructure might unlock in the future

[00:43:33] - How to screen out people for their potential to deliver transformative technology

[00:45:38] - What he’d like to know about the future that he isn’t sure of yet 

[00:47:45] - Things he’s most intrigued about by cryptocurrencies as an infrastructure person

[00:51:36] - Where he’s most bullish and bearish relative to his peers in digital infrastructure

[00:52:49] - The kindest thing anyone has ever done for him

Jun 07, 2022
Aswath Damodaran - Making Sense of the Market - [Invest Like the Best, EP. 279]
01:55:12

My guest today is Aswath Damodaran, a Professor of Finance at NYU’s Stern School of Business. Aswath is one of the clearest teachers of investing and finance in our industry and through his blog, books, and YouTube has open-sourced his wisdom for decades. This conversation is a masterclass of key investing concepts. We discuss inflation, narratives, disruption, the evolution of alpha and edge, and his thoughts on ESG. Please enjoy this great conversation with Aswath Damodaran.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:43] - [First question] - How he thinks about inflation as a now dominant force

[00:04:33] - Why inflation is so important across the spectrum

[00:09:02] - Big lessons from other periods of historically high inflation writ large

[00:10:45] - Reasons why equities as an asset class struggle in high inflation environments

[00:15:21] - The relationship betweens goods versus services in times of high inflation

[00:16:59] - Broader economic implications especially for income inequality

[00:19:03] - The Fed taking inflation seriously now when they didn’t and thoughts on the policy response to today’s situation

[00:21:05] - How smart companies are defensively adjusting to inflation

[00:24:38] - Thoughts on returns on invested capital with emphasis on invested capital 

[00:27:46] - The importance of a capital allocation skill-set for executive team members

[00:29:32] - Further historic lessons and how he’s being defensive against inflation

[00:33:09] - Lessons learned about Amazon valuing them every year since their inception

[00:37:50] - How to figure out a new company’s narrative and the story they’re telling

[00:42:25] - Whenever he sees Thanos in the Avengers he thinks of Amazon

[00:44:51] - Thoughts on Facebook, Apple and Microsoft

[00:48:26] - The evolution of edge and the search for alpha

[00:54:37] - Whether or not there’s utility in studying other investors 

[00:57:16] - Skill versus luck and the most common valuation mistakes he’s made

[00:59:09] - Assuming long-term growth rates and changing company life cycles

[01:02:02] - Momentum and Value investing in today’s market

[01:07:24] - Differences between interest rates and discount rates in regards to inflation

[01:10:29] - Thoughts on equity risk premium in a market like this

[01:12:00] - How today’s market affects early stage equity investment

[01:14:36] - The growing popularity of ESG and his seemingly contrarian view on it

[01:24:03] - Nature of disruption as a force and companies that are protected from it

[01:28:24] - Assigning a disruption risk premium when valuing companies

[01:31:17] - Characteristics that will define the most successful leaders over the next decade

[01:32:52] - What he makes of Elon Musk buying Twitter

[01:34:24] - Other major topics he has a divergent view on 

[01:38:37] - Narrative And Numbers; The kindest thing anyone has ever done for him

[01:38:55] - Teaching with a goal of changing mindsets 

May 31, 2022
Anduril: Building the Future of Defense - [Business Breakdowns, EP. 59]
01:10:14

Today, we are running a special episode of Business Breakdowns. With geopolitics playing an increasingly important role in society again, this episode with Anduril’s CEO offers an inside look at the state of the defense industry and how it is changing. If you enjoy this episode, subscribe to Business Breakdowns on your preferred podcast player, where you’ll find past episodes on Block, Goldman Sachs, AutoZone and many others.

 

Today, we are breaking down Anduril. Anduril builds high tech defense systems for the US Department of Defense and its allies. Crucially, it does so with speed that emanates from Silicon Valley. Founded in 2017 by Palmer Luckey, who previously built and sold Oculus to Facebook, Anduril has achieved the rare feat of challenging the established order in the defense industry.

 

To break down Anduril, I’m joined by the company’s CEO and co-founder, Brian Schimpf. We discuss the history of the defense industry, how Anduril’s business is counter positioned against the legacy cost-plus model, and what Brian has learned about selling to the DoD. Please enjoy this breakdown of Anduril.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. If you're ready to go deeper on any company and you appreciate the value of primary research, head to tegus.co/breakdowns for a free trial.

 

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This episode is brought to you by Daloopa. Daloopa streamlines a major pain point for investors. By capturing all of a company's KPIs and adjusted financials into their database - Daloopa makes it easy to quickly update your models for what matters. Daloopa uses AI to find every KPI disclosed - from charts, to text, and even from footnotes of investor presentations. Daloopa updates these KPIs and data points in your existing Excel models in one click, regardless of your source or format. Test Daloopa for free at daloopa.com/Patrick.

 

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Business Breakdowns is a property of Colossus, LLC. 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

[00:02:52] - [First question] - The history of defense technology and the technological and competitive landscape when he set out to build Anduril

[00:08:22] - What the early experience was like when approaching the government and finding an early adopter

[00:12:44] - Necessity being the mother of invention when it came to developing drones

[00:16:37] - What it’s like to develop hardware and software products at the same time 

[00:20:26] - How the defense business complex works economically and overview of the detailed cost plus model

[00:24:44] - The state of military technology and military conflict today writ large

[00:31:10] - Are we heading to a future where warfare is mostly machine against machine? 

[00:33:34] - Comparing the ghost drone system to predator drones

[00:38:40] - Guiding principles as a firm and deciding on their product roadmap

[00:43:25] - An overview of their product lineup and what they’ve built so far 

[00:48:13] - Having an open innovation policy to promote competition

[00:49:37] - The nuance of politics when it comes to building and running their business

[00:51:56] - Most difficult decisions he’s had to make through Anduril’s history 

[00:53:51] - How he overcame Anduril’s lowest points and biggest challenges 

[00:58:38] - Thoughts on effectively compounding hardware innovation 

[01:02:23] - A moment he’s most proud of and regrets most in Anduril’s history

[01:04:20] - Lessons learned from observing Palantir and SpaceX 

[01:08:37] - The kindest thing anyone has ever done for him

May 26, 2022
Tobi Lütke - Embrace the Unexpected - [Invest Like the Best, EP. 278]
01:24:53

My guest today is Tobi Lütke, co-founder and CEO of Shopify. Having first spoken to Tobi at the beginning of the pandemic, just two months into it, this felt an opportune moment to revisit Shopify and the world through Tobi’s eyes. Among many things, we discuss Shopify’s evolution into the world of atoms-based building through Shopify’s fulfillment network, the value of infrastructure writ large, and the impact of market volatility on day-to-day business building. Please enjoy my conversation with Tobi Lütke.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

-----

 

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

 

Past guests include Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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 interest in infrastructure as a whole and why it’s underrated

[00:07:18] - Whether or not we’re currently building enough digital infrastructure 

[00:09:45] - Base level principles for decision making around building infrastructure 

[00:13:17] - How much room is left for innovation and whether or not we’ll just reinvent basic human instincts

[00:15:22] - Ways new ideas are fed into a product funnel at Shopify and greenlit

[00:19:34] - Solving eCommerce infrastructure and what he attributes to Shopify’s success

[00:24:23] - Overview of the Shopify Network and how it’s evolved over time 

[00:31:04] - Lessons learned in an atom-driven world in regards to fulfillment and logistics

[00:34:37] - Common ways bits thinkers are often wrong when solving atom problems

[00:35:50] - Spreadsheets tend to win meetings and how the ROI on a fulfillment network impacts its ecosystem

[00:40:26] - Navigating becoming an aggregator that sits on top of their merchants and whether or not there are plans to participate as a distributor

[00:45:45] - Fair market value, what it’s been like managing through such a volatile market, and important takeaways

[00:50:54] - Thoughts on capital allocation decisions as Shopify continues to grow

[00:53:25] - Advice for company leaders effectively communicating with their teams about stock-based compensation 

[00:59:04] - How much COVID altered their trajectory and what he’s most interested in as he looks out to the future

[01:03:45] - What he’s learned about blockchains and the crypto space given recent events

[01:08:45] - A new idea he’s encountered recently that he’s fallen in love with 

May 24, 2022
Tyler Cowen & Daniel Gross - Identifying Talent - [Invest Like the Best, EP. 277]
01:19:07

My guests today are Tyler Cowen and Daniel Gross. Tyler is an economics professor and creator of one of the most popular economics blogs on the internet. Daniel is the founder of start-up accelerator Pioneer, having previously been a director at Apple and a partner at Y Combinator. Both Daniel and Tyler are prolific talent spotters and that is the focus of our discussion and their new book, which is called Talent. Please enjoy this conversation with Tyler Cowen and Daniel Gross.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:38] - [First question] - Defining what talent is to them writ large

[00:03:34] - The differences between means and ends in regards to talent

[00:04:14] - What the Diet Coke idea is and why it’s relevant

[00:06:32] - Types of energy that are valuable and the subtle differences between them 

[00:07:40] - Thoughts on using a moneyball-like approach to acquiring and evaluating talent 

[00:11:49] - The talent market and thinking about pricing talent specifically

[00:13:14] - What is seemingly overpriced in today’s talent landscape

[00:15:50] - Relationship between experience and/or age when it comes to talent

[00:20:34] - Lessons about the utility of intelligence and where they’ve lead them wrong

[00:23:35] - What’s beneath being an outsider and why it’s important

[00:24:46] - Why what people do in their downtime is worth considering  

[00:28:27] - Whether or not references should be held in higher regard than interviews

[00:31:41] - Things to try and get out of a reference call as an objective

[00:32:40] - Disabilities and what lead them write that chapter specifically

[00:35:01] - Whether or not talented people are happier  

[00:38:40] - Lack of contentment and it’s dynamic influence over individuals

[00:41:01] - Where they think the other is most talented

[00:43:33] - Thinking about the physical side of mental performance

[00:45:49] - What was frustrating about writing the book

[00:48:25] - How they evaluate talent most differently now after having finished the book

[00:50:41] - What makes for a good bat signal and how to cast one well 

[00:53:27] - Personality inventories and what they would and wouldn’t recommend  

[00:54:15] - Geographical frictions and their role in high success rates

[00:56:08] - Antonio Gracias; Existing supply constraints on talent development

[01:00:01] - How they would redesign the current attractors of talent that we rely on today

[01:01:18] - Assembly line development and how we can improve and scale talent filters

[01:02:29] - The biggest open questions for talent today writ large

[01:05:16] - The kindest thing anyone has ever done for Tyler

May 17, 2022
Jeff Jordan - Building & Investing in Marketplaces - [Invest Like the Best, EP. 276]
01:20:08

My guest today is Jeff Jordan, General Partner at Andreessen Horowitz. Jeff has one of the most interesting set of experiences of guests that I’ve had on the show. As an operator, he has been the General Manager of eBay.com, President of PayPal, and CEO of OpenTable. As an investor, he was one of the first General Partners at a16z and sits on the board of Airbnb, Instacart, Pinterest, and other notable firms. Given his vast experience, he is the firm’s go-to-expert on all things marketplaces, which is the common thread in our conversation. Please enjoy this great discussion with Jeff Jordan.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:48] - The notion of perfect competition in marketplaces

[00:04:31] - How to build a marketplace while thinking about perfect competition

[00:05:32] - Promoting price discovery at eBay

[00:06:52] - Features of a marketplace he focuses on 

[00:08:38] - Best way to do lead generation 

[00:10:20] - Red flags for marketplace businesses 

[00:11:00] - Major business lessons learned while at Disney 

[00:12:10] - Learning to be an operator while at eBay; Leaving It All on the Field

[00:14:45] - How he got hired at OpenTable

[00:16:22] - Taking OpenTable public and being its first public company CEO

[00:17:44] - What they did well in financing OpenTable

[00:18:54] - Communications between company leaders and its investors 

[00:19:45] - Going from operator to investor

[00:22:08] - Lessons from the early years of becoming an investor and pricing companies

[00:24:12] - Power of network effects on a startup

[00:26:56] - Healthy tensions inside of a network

[00:29:23] - When the supply side is the more difficult part of the equation

[00:30:27] - Characteristics of founders when it comes to marketplaces

[00:33:30] - The importance of being a perpetual learner as a founder

[00:35:36] - When he starts focusing on unit economics and margin profile in a new marketplace

[00:37:45] - Increasing convenience for a buyer as a business strategy 

[00:42:14] - Categories that could use better marketplace solutions

[00:44:36] - Layers of growth inside a business

[00:50:26] - Lessons with the unique business model of Pinterest

[00:52:03] - Unique aspects of the Andreessen Horowitz business model

[00:55:54] - Finding and recruiting talented general partner investors 

[00:57:37] - The morning basketball game and community strengthening

[01:01:36] - Defining great mentor relationships

[01:04:54] - Kindest thing anyone has done for him

[01:06:05] - Lessons from his parents

May 10, 2022
Eric Glyman - Reimagining Corporate Finance - [Invest Like the Best, EP. 275]
01:01:23

My guest today is Eric Glyman, co-founder and CEO of Ramp. Ramp is best known for its corporate cards but it has a range of software products to help finance teams save money and time. Since its founding in 2019, the business has grown rapidly and was last valued at $8 billion. Eric and I discuss Ramp’s initial marketing wedge, how the business has dealt with such fast growth, and why they hold stablecoins on their balance sheet. Please enjoy my conversation with Eric Glyman.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:41] - [First question] - What was most notably awry about the industry before Ramp

[00:04:45] - Breakdown of Visa; The business model of the Black Card compared to the business card offering of Ramp

[00:08:40] - Causes and what he attributes their early success to

[00:11:30] - Description of Ramp’s software in the beginning and the evolution of co-building it

[00:16:34] - How he’s gone about building the company and team fast enough to handle their explosive growth curve

[00:19:47] - Approaching all aspects of recruiting and acquiring such great talent

[00:21:39] - Thoughts on the biggest mistake he’s made while building Ramp

[00:24:05] - Lessons learned about marketing that this journey has taught him

[00:26:13] - Learning to manage a senior team and advice for managing rapid growth

[00:28:58] - Unique aspects of Ramp’s approach to the financing side 

[00:32:56] - Why they are storing some of their balance sheet in stablecoins 

[00:34:47] - What the idealized end state of Ramp looks like

[00:37:26] - How the data and information he sees indicates trends in the economy writ large

[00:39:33] - Providing secondary liquidity to employees in a world where companies stay private for longer periods of time

[00:43:03] - Aspects of company building that are still unnecessarily hard

[00:44:55] - What has him most excited about Ramp in the next 12-18 months

[00:46:42] - The kindest thing anyone has ever done for him

May 03, 2022
Dmitry Balyasny - Building a Better Model - [Invest Like the Best, EP. 274]
01:12:33

My guest today is Dmitry Balyasny. Dmitry is the Managing Partner and CIO of Balyasny Asset Management, otherwise known as BAM. BAM runs a multi-strategy, multi-PM model that aims to produce consistent absolute returns. Since its founding in 2001, it has produced only one negative year and become one of the largest firms of its kind. Please enjoy my conversation with Dmitry Balyasny. 

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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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. Listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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 origin story of his firm and the key stages of evolution

[00:06:43] - Describing the difference between good and great in platform hedge funds 

[00:10:25] - How a multi-strategy, multi-investor group works and managing capital allocation

[00:13:58] - What he’s trying to solve at the end of the day as their CIO

[00:16:21] - How close they are to their idealized end-state 

[00:18:26] - Typical amounts of leverage associated with these types of models

[00:20:22] - Lessons learned about incentivizing talented investors

[00:22:39] - Ways he tends to attract risk takers and their levels of variance

[00:28:15] - Other characteristics that are common amongst great PMs

[00:30:42] - The nature and source of edge and how it’s changed most over time

[00:33:19] - Some of the hardest portfolio and business decisions he’s had to make 

[00:37:59] - One of his most important business decisions on the firm side

[00:40:09] - How they’ve thought about shorting as a firm in general and more recently

[00:43:52] - How interest rates affect this style of investing

[00:45:29] - His view on the opportunity set in private markets and what does and doesn’t excite him about it

[00:49:42] - How reading Ayn Rand most shaped his thinking

[00:50:36] - Things Ayn most got right and most got wrong in his mind

[00:51:24] - What the war in Ukraine has felt like for him as a Ukrainian-American

[00:52:08] - Ways the future still has him excited as he continues to build his firm

[00:53:53] - Where his trading instincts draw him today and areas of interest

[00:55:11] - His most memorable trade of all time

[00:56:37] - In which order the major asset classes will be affected by digital innovation

[00:58:13] - The kindest thing anyone has ever done for him

Apr 26, 2022
Henry Ward - Transforming Private Markets - [Invest Like the Best, EP. 273]
01:21:43

My guest today is Henry Ward, co-founder and CEO of Carta. Started in 2012, Carta helps companies and investors manage their cap tables, equity plans, and ownership. Last year, they launched CartaX, a platform for private companies and their employees to access secondary market liquidity. Our discussion is a detailed exploration of private market infrastructure and Henry’s views on building an enduring business. Please enjoy my conversation with Henry Ward.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

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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. Listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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 first key mental moment of how Carta came to him

[00:05:30] - Initial thoughts on how to position Carta as a business model

[00:06:47] - Historical divergence between private and public market infrastructure

[00:08:33] - What a price discovery process for primary shares could look like in the future

[00:11:09] - The end state Carta is trying to effect in their perfect state

[00:13:29] - Why it’s so hard for private company staff to manage their illiquid wealth

[00:15:45] - Lessons and challenges in the new market creation business

[00:17:57] - The nature and dynamics of supply and demand in this space

[00:20:16] - Restrictions that prevent retail investors from participating in private markets and why there’s more alpha in private markets

[00:22:45] - How Carta is mapped onto the success of its customers

[00:25:27] - Deciding on what is a good idea and what isn’t when it comes to focus

[00:28:07] - Describing the One of N versus N of One market frameworks and principles of this philosophy that manifests in how he runs Carta

[00:32:11] - How working at Carta would differ from a payroll-type company

[00:35:37] - Characterizing his leadership and management styles

[00:37:57] - The types of circumstances that bring out his tough side

[00:39:33] - Making hard decisions in a bottom up management model 

[00:44:05] - How he spends his time while building Carta

[00:45:02] - What a great product looks like to him

[00:47:10] - The Systems Bible; Defining what a great team looks like

[00:49:13] - What he’s learned about being great at Go-To-Market

[00:51:26] - Effective ways to beat competitors and build relationship pipelines

[00:53:49] - Things he likes the least about leading a company of this size 

[00:55:13] - What he fears most as he thinks about the future of Carta

[00:55:45] - Advice for entrepreneurs when thinking about data in modern businesses

[00:58:26] - The biggest missing pieces in capital market structure writ large

[01:00:17] - What’s next for CartaX and what he’ll be pushing to make it work 

[01:02:10] - Lessons learned from serving venture investors 

[01:04:25] - Whether or not investment banks are their competitors

[01:05:18] - Public market dislocation and how long it will last

[01:06:58] - The kindest thing anyone has ever done for him

Apr 21, 2022
Alexandr Wang - A Primer on AI - [Invest Like the Best, EP. 272]
01:12:26

My guest today is Alexandr Wang, the CEO and founder of Scale AI. Alexandr founded Scale in 2016, having been inspired to accelerate the development of AI through his work at Quora and his studies at MIT. Specifically, Alexandr realized there was a lack of infrastructure solutions for producing high quality data, the lifeblood for AI models. Today, Scale provides data solutions to leading AI teams at Meta, Microsoft, OpenAI, Flexport, the US Air Force, and many others. This time last year, the business was valued at over $7 billion. 

 

Our conversation is a primer on AI. We discuss the building blocks beneath successful artificial intelligence, AI’s role in both the public and private sector, and why data is the new code. We also cover the similarities and differences between AI and software from an investing perspective and what inspiration Scale takes from AWS. Please enjoy my great discussion with Alexandr Wang.



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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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 role that AI and data play in geopolitics and foreign policy

[00:07:21] - The end state of a digital arms race akin to nuclear weapons

[00:08:53] - Current state of things writ large and how the public and private sectors differ

[00:11:33] - The flow and importance of talent when scaling AI and whether it’s more important than software 

[00:14:29] - His thoughts on how to communicate categories of what AI can do well and what is still a ways out

[00:20:18] - The process of creating an AI model and the stages of development

[00:23:19] - A growing trend of data becoming more valuable than code itself

[00:27:16] - Principles of building a great engine for gathering data

[00:29:04] - The state of technology around annotating data writ large

[00:31:31] - What Scale does as a business and their product lineup

[00:35:08] - The Storage and Compute equivalents in the AI space

[00:37:08] - How Scale fills the gap in producing better and cleaner data

[00:39:52] - What Scale will look like in 10 years if their vision is fully realized

[00:41:11] - Where AI is in the S curve of acceleration and where AI and software intersect

[00:44:32] - Questions to ask about how to incorporate AI and data sets in your business

[00:46:23] - What worries him about the proliferation of technology that makes AI more accessible to the masses

[00:48:27] - The most interesting AI model he’s ever come across and collapsing the friction between human intent and programmable outcomes

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

Apr 12, 2022
Antonio Gracias - Pro-Entropic Investing - [Invest Like the Best, EP. 271]
01:11:44

My guest today is Antonio Gracias, founder, CIO, and CEO of Valor Equity Partners. Antonio is perhaps best known for his role at Tesla, as the earliest institutional investor and Director from 2007 to 2021. But he has deep operating and investing experience, having first acquired and managed a number of manufacturing and technology companies during his 20s. And it was during those formative years that Antonio and his team developed the skills that led to Valor, which provides operational expertise to the high growth private companies they invest in.

 

Our conversation is a deep exploration of the drivers behind Antonio and Valor’s success. We dive into his concept of pro-entropic investing, what he learned as a 25-year-old running a manufacturing business, and trust me when I say, you don't want to miss his answer to the kindest thing ever. Please enjoy this great conversation with Antonio Gracias.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick

 

-----

 

This episode is brought to you by Lemon.io. The team at  Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - Defining what a pro-entropic company is

[00:07:26] - Understanding external forces of chaos and why they’ll continue to increase

[00:11:32] - What he’s learned about identifying and investing in pro-entropic companies

[00:13:43] - Investing with entropy in mind can be a bet on unchanging aspects of human nature

[00:15:08] - Defining durability in contrast with resiliency and entropy

[00:17:27] - Timing and valuation matters less and less as you ascend the entropic scale

[00:18:53] - Coming from a traditional background and the origin of Valor

[00:22:05] - The theory of constraints and why it’s so powerful; The Goal

[00:26:32] - Transitioning into a private equity structure and Valor’s 2001-2005 era

[00:30:42] - Asymmetric information and developing a stage deployment of capital strategy

[00:32:51] - The importance of understanding people and psychological ideas for investing he finds useful

[00:36:59] - Understanding the psychology of founders that have successful outcomes

[00:39:07] - Vision setting, narrative building, and qualities of effective and dangerous leaders

[00:42:02] - Decision making bias and combating bias effectively in practice 

[00:44:30] - Where security and control figures into his thinking

[00:45:45] - Identity in relation to ego; the tools he uses to combat identity related decisions

[00:49:04] - Lessons learned from the Japanese language versus Western languages

[00:50:37] - What he’s gotten better at when it comes to getting to the heart of what’s actually going on in a company and accepting reality

[00:53:07] - Questions he returns to when he’s getting to know a company

[00:56:16] - An episode of operational deployment that most stands out in memory

[00:58:54] - Key concepts that most stick with him from working alongside Elon Musk

[01:01:32] - Why there aren’t more Musk’s or Bezos’ in the world

[01:04:20] - Ensuring Valor invests in the best companies going forward

[01:06:06] - How to pass the torch of what Valor is to others when his time is done

[01:08:25] - The kindest thing anyone has ever done for him 

Apr 05, 2022
David Rubenstein - Life, Leadership, and LBOs - [Invest Like the Best, EP. 270]
01:15:10

My guest today is David Rubenstein, co-founder of The Carlyle Group - one of the largest private equity firms in the world. David has worked in the White House, built a $300 billion investment institution, become a prominent philanthropist, published books, and even hosts his own TV show. It was a thrill to sit down with him and cover the whole spectrum of his experience as a father, investor, historian, and titan of American business. Please enjoy this great conversation with David Rubenstein.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

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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. Listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:02] - [First question] - What his perspective on the world today is compared to the last forty years

[00:05:35] - The long term implications of the Ukraine war on a global scale

[00:07:54] - Concerns and thoughts on the US’s role in a radically different world

[00:10:07] - How inflation and reduced globalization impacts business behavior in the US

[00:12:58] - Why he chooses to learn by listening to people who are incredibly versed in their respective fields and what started it

[00:14:11] - His method when interviewing people and how it’s changed over time

[00:15:03] - How his interest in leadership as a topic began; How to Lead

[00:17:55] - The time he was the most personally in awe of a leader

[00:19:05] - The most basic ingredients for strong leadership

[00:21:34] - Learning from Oprah and developing his own interviewing style

[00:24:25] - His leadership style while running Carlyle and key variables that drove Carlyle’s success

[00:28:41] - The ways that were most effective in terms of investment for Carlyle’s brand

[00:29:50] - How should a new investor think about the relationship between government and business

[00:31:25] - Best ways for a business to interact with the government and common traits of those who do it well

[00:32:17] - What he’s learned about leadership that he thinks is the most portable for other people

[00:34:04] - His interest in masters of leadership and what he has learned from them

[00:35:08] - How Carlyle retained their talent and building relationships with LP investors

[00:37:20] - Lessons from working in media with what worked and what didn’t; How to Invest

[00:38:55] - How he approached writing How to Invest

[00:41:13] - The importance of intuition when evaluating backers and why geniuses aren’t always chosen

[00:43:04] - Big aspects of American history and why he finds it so interesting; The American Story

[00:44:17] - Key drivers of American outcomes and biggest areas for improvement

[00:47:00] - Lessons he learned going from humble beginnings to amassing wealth and how he’s teaching his children about it

[00:49:20] - The state of private equity and what are its best and highest functions today

[00:51:03] - Experience and impressions on the emerging cryptosphere

[00:52:25] - What makes for a good chairman and why he is always drawn to that role

[00:53:42] - The most interesting system outside of the US that he’s observed

[00:55:33] - What he has learned about being a giving pledge signer and philanthropy

[00:57:02] - His interest in Monticello and the Magna Carta

[00:59:13] - View on how speeches from leaders have changed over the years; Citizenship in a Republic

[01:01:24] - What subject he would write his next book on

[01:03:58] - Thoughts on the line between giving your life for your country versus your state

[01:05:17] - The American Experiment

[01:06:10] - Looking back on his career at a time where he felt the most alive

[01:08:07] - The kindest thing anyone has ever done for him

Mar 29, 2022
Gaurav Kapadia - Everything Compounds - [Invest Like the Best, EP. 269]
01:17:11

My guest today is Gaurav Kapadia, founder of investment firm XN. Gaurav is a veteran of the investing arena. We cover his lessons while rising to partner at TPG Axon, co-founding Soroban Capital, and his decision to launch XN in 2020. We then discuss his approach to building XN around a culture of rigor and kindness, the importance of relationships in investing, and finding investments that are obvious in retrospect. Please enjoy my great conversation with Gaurav Kapadia.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

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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. Invest Like the Best listeners can redeem a $1k off coupon at vanta.com/patrick

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:05] - [First question] - What lead to kindness and rigor becoming pillars in XN’s company culture

[00:05:30] - The types of situations where it’s hardest to be kind or rigorous 

[00:07:58] - Asking one question that can stump a founder can be a display of rigor

[00:08:58] - An example of looking at a situation and reducing the problem to a single variable

[00:12:51] - How he trains investors and team members to consider outcomes that would be obvious in hindsight

[00:14:28] - Developing the art of interacting with company management

[00:17:54] - Dimensions that typically find their way into his presentations and what tends to create complexity 

[00:21:13] - Whether or not rigor has declined in public markets over the years

[00:21:55] - Why fewer talented people are going into public markets

[00:23:01] - What it felt like when he first started XN and being successful at a young age 

[00:28:58] - Being impressed with his peers and rooting for each other

[00:30:33] - The nature of public versus private investing today writ large 

[00:32:32] - How he gets to know a company when he’s never heard of them before

[00:35:20] - Reasons he won’t invest from a personal policy standpoint

[00:36:01] - Common problems he encounters that companies are dealing with

[00:37:32] - Defining the strike zone of companies to invest in where he can be best-in-class

[00:39:10] - The insane valuations of public markets in recent years especially in tech

[00:40:42] - Why there are so few great businesses and common attributes of the great ones

[00:44:12] - Biggest problems in the investment industry writ large  

[00:45:48] - The most remarkable business he’s ever seen  

[00:49:22] - How he would teach investors to deploy XN’s operating partner model

[00:51:32] - His perspective and thoughts on diversity in the investing industry

[00:56:58] - A business or institution he would own outright personally 

[00:57:37] - What outside of investing most has his attention lately

[00:59:50] - Key touchpoints of coming from Queens and going to Hunter

[01:02:15] - What stands out looking back on his relationship with his parents and how hard they worked to build a better life for their family

[01:04:10] - Two things that manifest in a system that is seemingly rigged towards the wealthy and the problem with generational wealth

[01:05:29] - What has him most excited and optimistic about the future in the investing landscape today

[01:08:16] - Investing mentors deserve gratitude for believing in their pupils

[01:09:12] - The kindest thing anyone has ever done for him  

Mar 22, 2022
Marko Papic - A Multi-Polar World - [Invest Like the Best, EP. 268]
01:09:41

My guest today is Marko Papic, partner and chief strategist at Clocktower Group, where he leads the firm’s research on macroeconomics and markets. Marko has spent his career at the intersection of finance and geopolitics, making him a perfect person to speak to about current events in Ukraine and their potential impact further afield. Along with Russia and Ukraine, we discuss the Fed, inflation, China, the green energy transition, and the US’s position in the global order. Please enjoy this discussion with Marko Papic.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

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This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:48] - [First question] - His thoughts on what’s happened so far between Russia and Ukraine

[00:06:18] - The geopolitical motivations for Russia and what they can gain from the conflict 

[00:10:52] - How his impressions of warfare have evolved watching this play out

[00:13:45] - What to consider about nuclear war and different types of nuclear weapons

[00:16:31] - The economic warfare from the West against Russia and its implications

[00:21:06] - Whether or not the world is de-globalizing and how interconnected we all are

[00:24:45] - How we should view post-covid inflation, specifically in the US

[00:30:34] - The ways the Fed’s role has evolved 

[00:33:25] - Impacts of liquidity on asset prices and why it’s such a key factor in markets

[00:34:16] - China’s positioning and how the Ukraine conflict could alter their plans

[00:40:58] - Thoughts on Taiwan and how global supply chains might change

[00:44:47] - Why so few people believe that China has peaked; Young China 

[00:48:52] - His take on income equality in the US and why it’s the number one issue

[00:53:03] - What the US could do to improve itself as a country most going forward

[00:55:35] - Having a green energy transition view is crucial and the surrounding politics

[00:59:22] - The preconditions for doing well in atoms-based innovation

[01:01:13] - What he’s watching most carefully about the conflict in Ukraine

[01:02:51] - The kindest thing anyone has ever done for him

Mar 15, 2022
Garry Tan - Unwrapping the Gift - [Invest Like the Best, EP. 267]
01:00:13

My guest today is Garry Tan, founder and managing partner of early-stage venture firm, Initialized Capital. Before starting Initialized, Garry was a partner at Y Combinator, employee number 10 at Palantir, and co-founder of YC backed blog platform Posterous. Our discussion covers what’s missing in the investment world, how to best systematize venture investments, and what he learned from Paul Graham. Please enjoy my conversation with Garry Tan.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

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This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - Why he’s interested by software and the global brain

[00:06:23] - How the shift from global to local manifests in his investing and company activities

[00:11:42] - Ways to increase throughput that would benefit everybody in the investing world 

[00:17:13] - What software he would build if there were no limitations and what happens at the systems level of securing deals at Initialize 

[00:23:33] - Why there is no objective application process for early-stage capital and how much human judgment we can remove from approving funding

[00:26:49] - Shared characteristics amongst new inventions he finds favorable 

[00:31:49] - Whether he’s able to evaluate an idea without a prototype

[00:33:33] - Why travel planning software was the worst idea of 2012 and what he sees as the bad idea of today

[00:36:06] - The most common reasons for failure in these types of businesses

[00:39:07] - Is big enabling technology shifts what manifests in successful outcomes?

[00:40:37] - The role of media and how it intersects with investing

[00:44:29] - What he attributes to the success of his firm and thriving in chaos

[00:48:11] - Would he press a button that would have made his childhood easy, and whether he’s met founders who haven’t come across adversity in their lives 

[00:50:00] - His thoughts on the world today via the lens of his portfolio

[00:53:12] - The kindest thing anyone has ever done for him 

 

Mar 08, 2022
Eric Mandelblatt - Investing in the Industrial Economy - [Invest Like the Best, EP. 266]
01:18:05

My guest today is Eric Mandelblatt, founder and CIO of Soroban Capital, a $10 billion investment firm. While many of my conversations focus on technology and emerging industries, Eric has deep roots investing in the industrial economy, which made this conversation a fun change of pace. We discuss why energy and materials represent such a small share of the market today, how the global push towards decarbonization could have massive impacts on the industrial economy moving forward, and how Eric evaluates this dynamic opportunity set. Please enjoy this deep-dive discussion with Eric Mandelblatt.

 

Editor’s note: This conversation was recorded on February 15, before last week's invasion of Ukraine.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best in class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:01] - [First question] - Soroban’s history and why Eric is qualified to discuss industrial and commodity sectors

[00:04:37] - Overview of what their portfolio looks like today

[00:05:49] - How much of the commodity exposed equity sectors are owned by hedge funds

[00:08:03] - The key history points that makes industrials more interesting today

[00:11:17] - Commodity cycles, what drives them, the role CAPEX plays and how this world works

[00:17:38] - Thoughts on natural demand and the societal push towards decarbonization

[00:22:32] - How deeply one needs to know commodities in order to hold them

[00:23:57] - Big categories to explore as decarbonization becomes more accessible to consumers and the lack of nuclear investing

[00:28:50] - The resurgence of industrial production in the US

[00:32:21] - Rail networks writ large and if we can expect new ones in the future

[00:36:17] - The market gap between rail and technology businesses

[00:41:38] - Commodities and the ways they differ from railroads 

[00:43:47] - Comparing the differences between businesses within the commodity industry

[00:46:52] - Walkthrough of Alcoa’s business and how things like a carbon tax might affect an individual business

[00:52:55] - What is the portfolio manifestation of the fact it's impossible to forecast commodities historically

[00:56:08] - His view of the world in its current state and big things that matter

[01:00:25] - Thoughts on inflation as an investor in the commodity space

[01:01:42] - Utopian to dystopian takes on what growth looks like for the world

[01:04:28] - Juxtaposed positions in big tech against the industrial story

[01:08:45] - The kindest thing someone has ever done for him

Mar 01, 2022
Sebastian Kanovich - Powering Emerging Markets Payments - [Founder’s Field Guide, EP. 56]
41:09

My guest today is Sebastian Kanovich, CEO of payments company dLocal. Sebastian founded dLocal in 2016 to bridge the infrastructure gap between payments in developed and emerging markets. Since then, the initially bootstrapped start-up has enabled global merchants like Uber, Spotify, and Google to service billions of emerging market users. And in doing so, dLocal has created $10bn of equity market value, having IPOd last year. Our discussion covers dLocal’s playbook for facilitating payments in emerging countries, what Sebastian has learned about great API building, and how he challenges himself to improve personally. Please enjoy my conversation with Sebastian Kanovich.

 

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 Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders

 

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Founder's Field Guide is a property of Colossus, LLC. 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

[00:02:13] - [First question] - His take on global payments, what is interesting about this system today, and dLocal’s role within it

[00:04:06] - Approaching a country that could benefit from low-friction payments and the playbook for helping them improve their system

[00:06:10] - Differences between being an API business versus a protocol one

[00:07:13] - What companies handle these systems outside of emerging markets and why they haven’t entered the emerging market space

[00:08:59] - A specific example of the steps involved in getting a country integrated into global payments for an app or service provider

[00:11:22] - Whether or not they interact with consumers

[00:12:09] - The trading and foreign exchange component of global transactions

[00:13:16] - Country specific product teams and consolidating their process

[00:14:52] - What he would look for in early-stage payment companies to invest in

[00:16:23] - Defining excellent when it comes to working with regulators and regulatory environments

[00:17:53] - Their role in digital globalization and trends that might arise in the future

[00:19:52] - Ways that low-friction payments have helped accelerate regional innovation

[00:21:31] - The unit economics and costs of a single payment 

[00:24:05] - What the source of cost is to process a payment or transaction

[00:25:10] - Variables in currencies that make them desirable to work with

[00:26:38] - Lessons learned from distribution and customer acquisition of their service

[00:29:23] - Advice he would give to developers building API products

[00:31:16] - An example of wanting to build a function into an API that was never built

[00:32:40] - How they’ve been able to move and scale so fast

[00:34:23] - Ways their business could most improve

[00:35:14] - The operating system he uses to run the company

[00:36:38] - Ways he’s most improved or gotten better as a CEO over the years

[00:37:58] - Why deep humility is such an integral part of his character 

[00:38:30] - The biggest mistake they’ve ever made as a business and what they learned 

[00:39:20] - The kindest thing anyone has ever done for him

Feb 24, 2022
Frank Slootman - Narrow the Focus, Increase the Quality - [Invest Like the Best, EP. 265]
51:17

My guest today is Frank Slootman, Chairman and CEO of cloud platform Snowflake. Frank has become one of the most revered CEOs in business. Over the past twenty years, he has three times taken over emerging enterprise software businesses – first Data Domain, then ServiceNow, and most recently Snowflake - and led them across the chasm into large, billion-dollar businesses. Please enjoy this great discussion with Frank Slootman.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best in class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.



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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:33] - [First question] - How he evaluates the team of a company he’s working with

[00:04:48] - The pace of decisions made around changing team members 

[00:06:10] - Understanding the potential quality of outside leaders being brought into the company

[00:08:13] - How he characterizes great and constructive confrontation

[00:09:53] - What he’s found to be most effective in convincing senior talent to join a team

[00:11:36] - Ways he personally generates energy to sustain himself in this pace of business

[00:14:17] - How he fosters and nurtures healthy communication pathways

[00:15:36] - Narrowing the focus when evaluating a new product

[00:17:58] - Is it possible for a focus to be too narrow?

[00:19:31] - An example of a dazzling customer that he’s worked with 

[00:21:04] - Working backwards from a problem and building something that solves it

[00:23:03] - Building trust between a company and its customers over time

[00:25:37] - Overview of the base layer ingredients of trust

[00:28:12] - Sequential versus parallel processing and how they affect building trust

[00:30:22] - Lessons in successfully translating between engineers and business people

[00:32:58] - Crossing the chasm and effective sales organizations

[00:35:17] - Working compensation into getting more out of an organization

[00:38:45] - How much a sales organization needs to work backwards to serve their product

[00:41:40] - Great questions for board members to ask their executive team

[00:46:07] - Where the analogy of ‘business as war’ falls down and defining the highlander concept 

[00:48:01] - What he feels he could still hone in his skillset 

[00:49:16] - The kindest thing anyone has ever done for him 

Feb 22, 2022
Tim Flannery - Simplifying Fund Closing - [Founder’s Field Guide, EP. 55]
50:56

My guest today is Tim Flannery, co-founder of venture fund administrator Passthrough. Passthrough is removing friction from the manual, time-consuming fundraising process by making investor onboarding as simple and automatic as possible. Their software helps investors fill out subscription documents in minutes rather than hours and allows GPs to easily track LP subscriptions during a fundraise.

 

In our conversation, we discuss the power of identity as a feature to build products around, the double-edged sword of solving an unsexy problem, and how Passthrough has thought about pricing their software. Please enjoy my conversation with Tim Flannery.

 

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 Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs so you can focus on what matters most — building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders

 

-----

 

Founder's Field Guide is a property of Colossus, LLC. 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

[00:02:08] - [First question] - The push and pull nature of what Passthrough is trying to solve

[00:04:17] - What the idealized end state 10 years from now looks like

[00:07:33] - A history of friction in investing and what barriers still remain today

[00:12:35] - The spark of insight that led to starting this new venture

[00:17:45] - Lessons learned from Okta and why identity is so powerful

[00:19:39] - Plans to expand this concept deeper into the tech stack

[00:22:24] - Adjacent problems that they plan to tackle as they continue to scale

[00:24:30] - What it feels like to use their product as an LP today

[00:26:10] - Working with service providers without becoming one

[00:28:06] - What great sales and distribution looks like to him at the infrastructure level 

[00:31:50] - Defining what “bring your collaborators” means 

[00:33:19] - His secret to recruiting talent to help solve an unsexy problem

[00:37:46] - His love for the intersection between process, pipelines, and efficiency 

[00:40:12] - Having a process for designing processes

[00:42:11] - How they arrived at their pricing and thoughtful pricing in software

[00:45:08] - Lessons from building Passthrough that other builders could benefit from 

[00:47:16] - The kindest thing anyone has ever done for him

Feb 17, 2022
Joey Levin - Building an Anti-Conglomerate - [Invest Like the Best, EP. 264]
01:09:08

My guest today is IAC’s CEO, Joey Levin. IAC is a unique business in that it’s a holding company which builds world-class digital businesses. Since Barry Diller created IAC over two decades ago, it has produced 11 public companies, including Match Group, Expedia, and Live Nation. Today, the business is comprised of category-leaders like Angi, Dotdash Meredith, and Care.com.

 

Joey joined IAC in 2003 and became CEO in 2015. We talk about why he tries to avoid centralization between businesses, what he's learned from Barry Diller, how he approaches capital allocation, and so much more. This conversation serves as an excellent reminder that there’s no formula to company building. Everything is idiosyncratic and requires its own best decisions. Please enjoy this great discussion with Joey Levin.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best in class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

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This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening inside our bodies. And it was the only product that has ever made me willing to log food. If you want early access to become a Member of their private Beta, (the waitlist is currently 150K+ people), use this link – levels.link/PATRICK

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:05] - [First question] - The unique nature of IAC; the business of building businesses

[00:05:27] - The first business spun out of IAC and its bottom-up philosophy

[00:06:41] - The differences of IAC and how they manifest 

[00:09:39] - Agility and history of respecting the core functions of the internet

[00:12:36] - Simplified, faster, and larger choice digital experiences

[00:15:57] - His thoughts on the shared characteristics amongst their winners 

[00:18:26] - Lessons from building competitive products in online dating simultaneously

[00:21:37] - Navigating customer acquisition cost and embracing change

[00:24:04] - What makes someone great at customer acquisition 

[00:26:26] - Fostering a unique approach compared to typical customer funnels

[00:27:48] - What most explains his move from a pip-squeak to CEO

[00:29:44] - The process he uses to get to know the critical aspects of a new business

[00:31:59] - Indications that a leader may no longer be suited to run a business

[00:33:13] - Characteristics of vertical markets that he finds attractive to get involved in

[00:34:08] - The early stages of incubating a new business and an overview of their process

[00:38:10] - Enabling new consumer experiences and infrastructure fading away

[00:40:17] - Distilling big ideas down to streamlined approachable consumer products 

[00:42:22] - High-level internal conversations around capital allocation

[00:45:06] - Quantitative versus qualitative analysis in their decision-making process

[00:46:50] - What idea felt the most right but turned out to be a disaster

[00:51:26] - Brand rollup versus brand consolidation and when either strategy is appropriate

[00:54:03] - Having a good sense of identifying, defining, and positioning categories

[00:56:23] - Which aspects of his perspectives have shifted since becoming CEO

[00:57:59] - Thoughts on the toolkit available for sourcing and the cost of capital

[01:01:08] - What personally brings him the most joy in what he does

[01:02:37] - Working with Barry Diller and what it taught him

[01:06:39] - The kindest thing anyone has ever done for him

Feb 15, 2022
Peter Chernin - Betting on Passion - [Invest Like the Best, EP. 263]
57:40

My guest today is Peter Chernin, who’s had a Hall of Fame career in the entertainment business. Peter ran News Corp and Fox for fifteen years between 1996 and 2009 before co-founding The Chernin Group, which has become one of the leading investment firms in the consumer space. Along the way, he has also produced a number of blockbuster films, including Titanic, Avatar, The Greatest Showman, and The Planet of the Apes Trilogy. Please enjoy this wonderful discussion with Peter Chernin.

 

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 20,000 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 Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies. And it was the only product that ever made me willing to log food. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - Business and investing lessons from producing Titanic and Avatar

[00:06:44] - Defining great content and why James Cameron’s franchises have done so well

[00:10:26] - Contributing factors to box-office domination of pre-existing franchises

[00:12:56] - Tailwinds in his earlier career and identifying them in time to get behind change

[00:16:07] - Identifying Showcase was a subscription business early on, unlike broadcast businesses

[00:19:40] - Signals of passion and how powerful niche audiences can be 

[00:23:24] - What a phony aggregator is and the slow dissolution of the middle market

[00:27:01] - The era of unbundling and direct relationships with superfans

[00:30:27] - Lessons learned from building Hulu

[00:34:29] - Working with Rupert Murdoch and qualities that separate him from the crowd

[00:37:07] - Defining what bravery means in a businesses sense

[00:39:22] - A movie he’s made in the past decade that he’s most proud of

[00:43:27] - The keys to being an effective partner to creative individuals

[00:49:53] - What exists today that may change the future landscape of media writ large

[00:52:19] - The kindest thing anyone has ever done for him

Feb 08, 2022
John Pfeffer - Adapt and Evolve - [Invest Like the Best, EP. 262]
01:53:07

My guest today is entrepreneur and investor, John Pfeffer. John was a partner at private equity firm KKR in the 2000s, Chairman of leading French IT company Groupe Allium in the 90s, and now invests his own money through his private family office, Pfeffer Capital.

John is one of the smartest investors I know, and our conversation spans all of John’s experience and investment ideas. We discuss the difference between value creation and wealth creation, why John has made such a big bet on one asset, and why adaptation is more important than ever. I hope you enjoy this conversation as much as I did.

 

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 20,000 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 Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:08] - [First question] - John’s background and the experiences that shaped his worldview and sparked his curiosity

[00:07:34] - Aspiring to grow with a lack of inertia 

[00:10:31] - Why he invests primarily in technology and technology dependant businesses [00:15:22] - What it’s felt like being a tech investor from 2011 leading up to today

[00:19:26] - How he defines good and bad business

[00:21:24] - Why good businesses don’t often have technology disruption risks

[00:22:26] - An (Institutional) Investor’s Take on Cryptoassets; key points from his paper

[00:35:28] - What else is interesting in the crypto space and potentially strong business models that exist outside of Bitcoin 

[00:48:46] - How capital has changed over time and what makes capital efficiency or formation superior

[00:51:51] - Value creation and why a shift in value can affect your returns

[01:01:12] - Whether or not crypto and the founding protocols will fade out of the public eye

[01:11:52] - A consensus on store of value in crypto and how it could change

[01:18:03] - Why he is so heavily allocated to Bitcoin compared to other tokens

[01:25:19] - General take on the nature of buying and selling capital and European markets

[01:35:28] - The interconnectedness of the globe and the future of globalism

[01:39:46] - Why he doesn’t ask people where they’re from and how he prefers to get to know people that can sometimes be unorthodox

[01:41:59] - Market index investing and why it may not be the best strategy going forward

[01:47:36] - The kindest thing anyone has ever done for him



Feb 01, 2022
Geoffrey Moore - Building Gorilla Businesses - [Invest Like the Best, EP. 261]
01:15:04

My guest today is the renowned tech author, consultant, and venture partner at Wildcat Ventures, Geoffrey Moore. Geoffrey has spent his career focused on the dynamics surrounding disruptive innovations and his book, Crossing the Chasm, has become a canonical work for young businesses trying to unlock mainstream markets.

 

This discussion is a masterclass on business strategy. We start with Geoffrey’s more recent work on category-defining businesses, break down his life cycle of adoption framework, and close with the ways messaging should change as a company evolves. Please enjoy this great discussion with Geoffrey Moore.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick



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This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:08] - [First question] - What he means by a gorilla business

[00:07:10] - An example of how companies self-organize into gorillas, chimps, and monkeys

[00:09:41] - Why architecture is so important and how it applies to company building 

[00:13:11] - How and when businesses should think about open and closed systems

[00:14:50] - Ways in which enabling tech companies are superior to application ones

[00:16:39] - Thoughts on approaching and hiring a singular use case company 

[00:18:23] - Markets underestimate competitive advantage periods for technological gorillas

[00:20:38] - The inertia and duration of being the creator of a space’s architecture

[00:23:28] - Advice for early-stage companies when creating or dominating categories 

[00:25:16] - What he’s learned about identifying trapped value 

[00:26:49] - Questions that can identify trapped value, factoring for time, and horizontal uses

[00:41:49] - Problems with risk exposure in B2B and applying this model for value creation

[00:33:37] - His initial discovery of the life cycles of adoption and its five categories

[00:39:29] - Perspective on venture capital funding and going from idea to the chasm

[00:44:10] - What good pragmatists in pain look like 

[00:47:29] - Successful vertical uses-case sales motions

[00:50:03] - Guarding from becoming over-specialized in a singular focused effort

[00:50:52] - The Diffusion of Innovations; Ways messages work their way through a company to keep up with category evolution 

[00:55:00] - How extensible these ideas are to non-technology businesses

[00:56:04] - The race between innovation and distribution 

[00:56:44] - What about the world today has changed or influenced his thinking

[00:59:17] - Ways big companies can stay competitive in emerging categories

[01:02:23] - The company he’s most enjoyed studying over his career 

[01:05:25] - Shared characteristics of exceptional leaders he’s met and talked to

[01:07:48] - The Gorilla Game, Crossing the Chasm

[01:08:14] - The kindest thing that anyone has ever done for him

Jan 27, 2022
Gavin Baker - The Cyclone Under the Surface - [Invest Like the Best, EP. 260]
01:19:31

My guest today is past guest Gavin Baker, managing partner and CIO of Atreides Management. Gavin’s focus is on consumer and tech growth investing, which makes him the perfect person to discuss the bloodbath we’ve seen in many growth equities over the past few months. We also cover inflation, semiconductors, and the disconnect between private and public markets. Please enjoy this conversation with the always great Gavin Baker.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:30] - [First question] - What it’s been like investing over the pandemic 

[00:06:14] - The way he thinks about multiples, how they’ve done, and where they’re going

[00:09:14] - Themes that most have his attention in our current economic landscape

[00:19:25] - The ways in which wage inflation negatively impacts the market

[00:25:39] - How semiconductors have evolved and what matters in that subsector

[00:32:47] - Software volatility and the roller coaster it's been on lately

[00:35:52] - A future state where infrastructure overtakes apps 

[00:41:03] - Key differences between internet and software and how they behave

[00:43:44] - The coming trend of the metaverse and his reaction to public adoption

[00:49:26] - Investor and business opportunities in adopting tech trends

[00:53:54] - An unfolding mismatch between private and public market multiples

[00:57:17] - How the competitive landscape of venture capital might evolve

[01:05:54] - Differences in recruiting and training talent in private and public markets

[01:10:20] - Sci-Fi novels that he’s read recently; Dune, A Wizard of Earthsea, Culture, Hyperion 

Jan 25, 2022
Sam Englebardt and Richard Kim - Investing in Immersive Worlds - [Invest Like the Best, EP. 259]
01:20:17

Today, my guests are Sam Englebardt and Richard Kim, general partners at venture fund, Galaxy Interactive. Having come from the media and finance sectors, respectively, Sam and Richard joined forces in 2018 to invest in their shared thesis that immersive digital experiences would become the dominant way people engage with each other in the future.

 

Our conversation centers around the evolution of art, finance, and gaming as they proliferate in Web3. Please enjoy my conversation with Sam and Richard.  

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.

 

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This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK

 

-----



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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:50] - [First question] - Their thoughts on the digital art market

[00:11:33] - What motivates traditional art collectors and what has been carried over into digital art

[00:17:27] - Is there an attractive beta opportunity in the digital art space?

[00:24:32] - Why investors should do more work understanding NFTs and ways to consider incorporating them into your portfolio

[00:27:55] - The history of Galaxy and their thesis writ large 

[00:33:09] - Exciting and terrifying aspects of the financialization of everything

[00:37:27] - Places where inserting markets could be beneficial with Web3

[00:45:27] - Their perspectives on gaming as a subcategory of Web3

[00:51:38] - Tokenomics and the importance of building great game communities

[00:59:18] - What we can learn from successful gaming companies and in-game monetization

[01:04:19] - How Diablo 3’s auction house detracted from the core player experience

[01:06:36] - Where they disagree with the Web3 investing community

[01:10:37] - The kindest things anyone has ever done for them

Jan 20, 2022
Ricky Sandler - Building an Investment Compass - [Invest Like the Best, EP. 258]
01:08:00

My guest today is Ricky Sandler, founder of Eminence Capital. Ricky is a hedge fund veteran managing over $8bn of assets across Eminence's strategies. We cover Ricky's evolution as an active investor, why he thinks this is a stock-picker's environment, and what keeps him competitive after a long and successful career. Please enjoy my conversation with Ricky Sandler.

 

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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.

 

-----

 

This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies - and it was the only product that has ever made me willing to log food. If you want early access to become a member of their private beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:42] - [First question] Whether or not great investment firms should be led by a single investor

[00:03:25] - Episodes where singular investment power has proven effective and powerful

[00:05:06] - Where he finds joy in the investing process on a regular basis

[00:06:19] - Ways he’s learned to become better at guiding and helping teams he works with

[00:08:14] - The most common types of fool's gold he comes across

[00:11:00] - Evolution of the pricing mechanisms in ever-evolving markets

[00:16:14] - Common features of a good mispricing opportunity

[00:18:42] - How he interacts with other hedge funds and long-only investors

[00:21:14] - An investor he often disagrees with but loves talking to 

[00:22:13] - The investment he’s most proud of historically

[00:25:11] - What the healthy draw that keeps him coming back to investing is

[00:28:31] - His opinion on crossover funds and their growing popularity

[00:32:09] - What the world in 2022 looks like to him and what both excites and worries him

[00:38:19] - Key contributors that influence liquidity and how it flows into equity prices

[00:41:26] - A macro view of the healthcare sector and why it’s so interesting today

[00:42:59] - Lessons from the Titans

[00:43:52] - Advice he’d give to younger investors for stepping into the space 

[00:46:45] - The kindest thing anyone has ever done for him

Jan 18, 2022
Orlando Bravo - The Art of Software Buyouts - [Invest Like the Best, EP. 257]
01:05:12

My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo.

 

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 20,000 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, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - His belief about an opportunity/capital mismatch in private equity

[00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities

[00:06:13] - Differences between software businesses they invest in versus traditional ones

[00:08:25] - Outline of how he runs their four-hour portfolio meetings

[00:09:53] - Overview of the very first deal he ever made in the software sector

[00:14:01] - The dissonance between the average SaaS company and the ones they try to manage

[00:18:22] - Major contributors that allow for their higher margins

[00:20:16] - Common mistakes of companies that mis-invest capital for growth only

[00:22:28] - Defining what market leader means writ large

[00:23:45] - Why the subsector of cyber security is such a good opportunity set

[00:26:25] - The evolving nature of the private equity world in general

[00:28:41] - Where returns will come from going forward

[00:31:47] - How good the opportunity for returns in this style of investing today is

[00:35:32] - Lessons learned on knowing when to exit or sell a position

[00:37:59] - How short their holding periods can be and how much influence they can have in such a short time

[00:40:04] - Surprising things about deal-making that he’s learned over his career

[00:41:20] - Difficulties and points of frictions in deals that still exist for him today

[00:43:11] - What part of the deal-making process he loves the most

[00:44:30] - If your job title has a C in it you’re not allowed to complain about it

[00:46:27] - Deeply held beliefs about operating excellence

[00:47:33] - What the word service means to him given everything we’ve talked about 

[00:50:27] - How we do a better job of inviting talent into this space

[00:52:51] - How decentralization will define the 2020s and beyond

[00:55:48] - What is most interesting about Web3 that might affect cyber security

[00:57:42] - Where there is a lack in innovation in private equity today

[01:00:45] - Advice for young talent for building their careers

[01:03:16] - The kindest thing that anyone has ever done for him

Dec 28, 2021
Nick Saltarelli - One Foot in Front of the Other - [Founder’s Field Guide, EP. 54]
01:09:01

My guest today is Nick Saltarelli, co-founder of the functional chocolate bar business, Mid-Day Squares. Nick started the company with his wife and brother-in-law a few years ago to build on a simple idea: if the big chocolate bar brands were to start today, what would they look like?

 

In our conversation, we discuss the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every day. Please enjoy this unique conversation with Nick Saltarelli.

 

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 Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders

 

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Founder's Field Guide is a property of Colossus, LLC. 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

[00:02:01] - [First question] - What Mid-Day Squares is and how he started the business

[00:04:48] - Why they’re so publicly open about their company’s goals

[00:09:05] - Major lessons he learned from his father’s early passing and being around very successful entrepreneurs at a young age 

[00:16:51] - What long term thinking unlocks for him in short term progress

[00:21:05] - Becoming unexpectedly close and learning from Rory Olson 

[00:25:44] - What Rory taught him about deal-making

[00:28:35] - Lessons from Rory about raising capital

[00:33:25] - Opportunities in a seemingly oversaturated market like chocolate

[00:42:46] - An example of doing something contrarian that worked out

[00:47:11] - Their unique approach to marketing Mid-Day Squares

[00:57:33] - Lessons learned about building a manufacturing operation after years in China

[01:02:35] - What we can expect from Mid-Day Squares in the near future

[01:06:59] - The kindest thing anyone has ever done for him

[01:08:05] - Mid-Day Squares Uncensored Podcast

Dec 23, 2021
Jenny Johnson - Seven Decades of Investing Expertise - [Invest Like the Best, EP. 256]
01:03:09

My guest today is Jenny Johnson, President and CEO of one of the world’s largest asset managers, Franklin Templeton. Jenny joined the business in 1988 and has worked in the organization ever since. In early 2020 she became CEO of Franklin, which now manages some $1.5 trillion. I should, of course, note that I met Jenny as our two firms explored a partnership, which we cemented 3 months ago when we announced that Franklin Templeton would be acquiring O'Shaughnessy Asset Management.

 

During our conversation, we discuss Jenny’s thoughts on leadership, how she manages the needle-moving problem that afflicts many large companies, and the ways in which she sees private markets becoming more accessible to retail investors in the future. Please enjoy this great conversation with Jenny Johnson.

 

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 20,000 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.



-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:19] - [First question] - The four P’s of leadership and what she thinks are the most important roles of a CEO 

[00:06:00] - The difficulty of finding and recruiting great people and keeping them invested 

[00:07:18] - Things she looks for in her senior leadership team

[00:07:59] - Knowing when to be more or less involved as a leader

[00:09:30] - Her takeaways from working in a family-owned business

[00:11:20] - Advice she’d give to families who are building businesses together

[00:12:06] - Thoughts on the role technology will play in the asset management industry

[00:16:13] - Costs and frictions that blockchains could alleviate

[00:18:17] - General views on disruption and considering ones position when thinking about the future

[00:20:09] - Knowing when to start a project internally or acquire an existing project

[00:23:10] - The hardest things about effective M&A decisions

[00:23:42] - Overseeing a hybrid model of singular focus between multiple investment groups

[00:28:26] - The pros and cons of active management against passive adoption

[00:31:15] - Costs and fees in the industry and how they might change in the future 

[00:33:04] - Talking to clients when they don’t have one specific view on strategy

[00:34:57] - When consensus is helpful and appropriate for making important decisions

[00:36:10] - Formative experiences in her career that has shaped her worldview

[00:38:34] - Managing emotions through seemingly chaotic situations

[00:39:13] - The impacts on psychology when being a top performer and an average one

[00:41:15] - Managing and adapting strategy when faced with highs and lows 

[00:42:55] - Acquiring alternative managers and defining what alternative assets are

[00:46:26] - Relevant trends on how capital is pooled and their client base over time

[00:47:52] - What is under-discussed in the world of asset management today writ large

[00:49:01] - Other leaders she’s met or knows that have had her in awe

[00:50:30] - What about Cathie Wood has made her story and approach so successful

[00:51:38] - How she runs a great board meeting and ways to improve meetings themselves 

[00:53:34] - Lessons learned about time management as the leader of a public company

[00:54:52] - What purpose means to her 

[00:56:18] - Ways we can incentivize young and new people to start investing

[00:59:10] - Her favorite things that her dad has taught her and how she’d describe him 

[01:00:57] - What has her most excited about the future  

[01:01:34] - The kindest thing that anyone has ever done for her

Dec 21, 2021
Doug Colkitt - The Evolution of Markets - [Invest Like the Best, EP. 255]
01:17:08

My guest today is Doug Colkitt. Doug has spent his career searching for and trading inefficient markets, first at Citadel’s high-frequency trading group, then for himself, and then as an operator building CrocSwap - a decentralized exchange or DEX designed to bring modern functionality to crypto markets, which is closer to what large traders have come to expect from a modern electronic market like the NASDAQ. 

 

My interest in market infrastructure has continued to grow since my great conversation with FTX founder Sam Bankman-Fried. So my conversation with Doug covers the evolution of market and trading infrastructure. We unpack the trading stack as it exists today, dive into DeFi’s innovations, and explore the new category of single contract DEXs that Doug is creating. After learning so much from Doug about how markets function and how crypto markets should function, I became an investor in his new business via my venture capital firm Positive Sum. Please enjoy this great conversation with Doug Colkitt.

 

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 20,000 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.



-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - Doug’s career and history working with markets

[00:08:55] - Defining what a trading stack is 

[00:13:41] - How HFT firms are such reliable money-making models

[00:16:27] - What’s at the cutting edge of traditional markets that provides an edge

[00:18:45] - The mechanical parts of infrastructure involved in building an exchange

[00:21:00] - Classes of data that matter for operating an exchange

[00:22:11] - Capacity and what good returns are as an HFT firm

[00:28:45] - Overview of the mechanics of an AMM

[00:31:53] - Earning a yield as a liquidity provider

[00:33:59] - Other ways to think about AMMs and liquidity providers

[00:36:42] - Key players in the AMM space and the evolution of them

[00:41:20] - How asset holders can approach DEX tools and be liquidity providers

[00:42:55] - The function of an exchange’s native token

[00:45:25] - Token distribution and how to earn them without buying them

[00:48:31] - How you receive payment for providing liquidity

[00:51:31] - What CrocSwap will do and what a single contract DEX unlocks

[00:57:36] - How CrocSwap is able to do this when other exchanges can’t

[00:59:27] - What single contracts will improve for users 

[01:00:43] - The impact CrocSwap will have for all participants writ large

[01:02:28] - Whether or not CrocSwap will cultivate an ecosystem

[01:03:30] - What’s next for CrocSwap in the near future

[01:04:58] - The promise of DeFi and the future of blockchain technology

[01:07:04] - Whether or not DeFi is a threat to centralized exchanges

[01:09:52] - Defining what MEV is and why it’s important for DeFi

[01:13:04] - Missing pieces in the DeFi world and how we can address them

[01:15:24] - The kindest thing anyone has ever done for him

Dec 14, 2021
Bill Gurley and Philip Rosedale - Back to the Future - [Invest Like the Best, EP. 254]
01:16:30

My guests today are Philip Rosedale and Bill Gurley. Philip created Second Life in the early 2000s and helped build it into the largest virtual 3D world ever created at the time. Frequent listeners will recognize Bill, who was an investor in Second Life via Benchmark Capital. During the conversation, we cover the fascinating story of Second Life and the billion-dollar economy that persists through to this day. Bill and Phillip share their key learnings from the experience, including the importance of usability, their views of the current metaverse opportunity, and what excites them most about the current focus on virtual realities. If you’re curious about what the metaverse might become, these two experts have seen much of this already and are kind to share their lessons with us. Please enjoy my conversation with Phillip and Bill.

 

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 20,000 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.

 

-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:22] - [First question] - The origin story of Second Life and why they created it

[00:05:38] - How many people were playing Second Life at its peak, the in-game economy and its growth trajectory

[00:06:49] - The interface between the in-game currency and its function for players

[00:10:53] - An example of early entrepreneurship and user-created IP in Second Life

[00:12:13] - Was technology a rate limiter to success in such an early version of the metaverse?

[00:14:35] - What was most exciting about creating it and it’s early-stage potential

[00:18:23] - Why Unity isn’t more adopted by creators and players like Minecraft

[00:24:42] - Defining what the metaverse means to each of them today 

[00:28:50] - What Discord has taught them about aggregating people digitally

[00:33:02] - Simultaneously crossing the digital chasm and the uncanny valley 

[00:38:16] - Key differences between games and platforms and the role of purpose

[00:42:04] - Why cryptocurrencies and blockchains haven’t produced experiences akin to the virtual Travis Scott concert

[00:47:13] - Why removing friction and centralizing financial structures can help growth and thoughts on play to earn gaming and user spending

[00:53:27] - Digital asset ownership and digital trustless exchanges in the metaverse

[00:57:30] - Pros and cons of today’s speculative digital asset valuations

[01:01:05] - Interesting pockets of opportunity that could benefit the metaverse ecosystem

[01:04:28] - How they’d build and construct an ETF with metaverse exposure

[01:07:18] - Thoughts on AR and VR and which holds more promise for public adoption 

[01:08:02] - Surprising findings about the role audio plays in digital worlds  

[01:10:23] - What they’re watching most closely in this emergent sector

[01:11:29] - Limitations of visual and sonic barriers when recreating real-world interactions 

[01:12:42] - The kindest things anyone has ever done for them 

Dec 07, 2021
Francis Davidson - Design-led Hospitality - [Invest Like the Best, EP.253]
53:22

My guest today is Francis Davidson, founder and CEO of the hospitality brand Sonder. Francis launched Sonder in 2013 as an alternative to traditional hotels and rentals with a specific focus on technology and design. During our conversation, we discuss where Sonder fits into the hospitality ecosystem and why design is so key to their offering. We also touch on Francis’s unique views around customer-centric focus, the nuances of hiring a team, and how they approach decision-making. Please enjoy my conversation with Francis Davidson.

 

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 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.

 

-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----



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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:38] - [First question] - Thoughts on the obligation of a business to deliver the best possible customer experience

[00:03:43] - Making a decision that actively went against improving the customer experience

[00:06:00] - What Sonder is and the key insight that led to building the business

[00:08:43] - Ways they cut down costs by leveraging technology available today

[00:10:44] - The economic model of the business and where it differs most from other hotels

[00:12:15] - The journey of $100 coming in to Sonder and working through the company

[00:13:20] - How the building or asset owner is integrated into the business model

[00:14:18] - Network density and how he thinks about it when it comes to scaling Sonder

[00:16:18] - His philosophy on design and why he thinks it matters in hospitality

[00:18:05] - What you can overspend on and underspend on to keep a guest happy

[00:21:05] - Making decisions on building in house or partnering to provide a new solution

[00:22:29] - Do property owners dress up their own hotels or are there guidelines and retailers

[00:23:51] - Lessons learned from working with overseas manufacturers

[00:24:44] - The key levers that will drive the growth of Sonder

[00:26:59] - What a typical occupancy rate is for them versus other hospitality options

[00:28:23] - Category creation and design that influence and change how people behave

[00:29:45] - Qualities of a new market and what drives success in attacking it

[00:31:15] - His contrarian viewpoint on building a business and talent density

[00:33:40] - The features of his job’s product and the interview process

[00:36:21] - Does everyone at a company need to be an A player?

[00:38:00] - His philosophy on team culture and developing synchronicity

[00:41:01] - Ways to build strategic competitive advantage inside of Sonder

[00:43:22] - What the most successful version of Sonder will look like ten years from now

[00:45:16] - New features and tech improvements that are coming soon he’s excited about

[00:46:48] - Trends in hospitality that have been accelerated and changed by COVID

[00:48:36] - Growing changes in the glamping and nature-forward guest experiences

[00:51:04] - The kindest thing that anyone has ever done for him 

Nov 30, 2021
Niraj Shah - Developing Every Skill - [Invest Like the Best, EP. 252]
01:04:09

My guest today is Niraj Shah, the CEO and co-founder of Wayfair. Wayfair started life in 2002 as a collection of independent websites selling category-specific home furniture but became a one-stop-shop for the home category in 2011 when, at $500 million in sales, the team consolidated their 240 websites into Wayfair.com. Today, the business offers 22 million products from 16 thousand suppliers to more than 30 million customers.

 

During our conversation, we discuss how the competitive frontiers in e-commerce have changed, what it was like to build out a proprietary logistics operation, and what makes the home goods market more attractive than other physical goods markets. Please enjoy this great conversation with Niraj Shah.

 

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 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.

 

-----

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:02:50] - [First question] - The global supply chain and its issues today in 2021

[00:05:13] - Why he finds the ocean leg such a problematic area and how to resolve it

[00:07:04] - Overview of the physical goods market around the world

[00:10:50] - The role of magazines and devout subscribers in certain sectors 

[00:11:50] - Are physical goods trends in flux or fairly steady and less geared to change

[00:13:06] - From 240 separate websites into what became Wayfair as we know it today

[00:16:36] - The competitive frontier of eCommerce in its early days and why they won 

[00:18:29] - Expanded logistics control, developing their brand, and becoming Wayfair

[00:21:40] - Aggressively building for the future as a public company with investors involved

[00:27:23] - Key differences between Wayfair, IKEA, Restoration Hardware and others

[00:34:22] - Other areas of interest and drivers of future investment opportunities for Wayfair

[00:38:39] - What excellent marketing means to him and why Netflix does it so well

[00:42:02] - The margin profile of Wayfair and all of its major components 

[00:47:13] - Lessons learned from major mistakes while building the business

[00:49:54] - Company culture and deliberately investing time and money into it

[00:51:50] - Evaluating the importance and success of their adapt and grow philosophy

[00:53:18] - How he would measure his own improvement as a CEO over time

[00:55:17] - Thoughts on the dimension of competition as they scaled

[00:56:57] - The most stressful episode of growing the business and what he learned 

[01:00:16] - What the best outcome for Wayfair would look like in the future

[01:01:38] - The kindest thing anyone has ever done for him

Nov 23, 2021
Bored Ape Yacht Club -  [Web3 Breakdowns, EP. 1]
51:56

Today, I am excited to share our newest show, Web3 Breakdowns. Similar to our Business Breakdowns series, Web3 will have it's own dedicated feed so make sure to hit this subscribe link or find it on your preferred podcast player. The first episode of Web3 Breakdowns covers Bored Ape Yacht Club. You will hear from guest, Eric Golden, who will also be coming back to host his own Web3 Breakdowns moving forward. We are sharing this first episode to make sure no one misses this launch. 

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Welcome to our new show, Web3 Breakdowns. We want to be your on ramp into this new decentralized world, and through conversations with builders, creators, and investors, we will do our best to help you understand and navigate this emerging ecosystem.

First up, we are breaking down the NFT project and cultural phenomenon, Bored Ape Yacht Club. To help break down Bored Apes, I am joined by Eric Golden, former Portfolio Manager at Fidelity and current Bored Ape owner. Eric and I start with an overview of the Bored Ape Yacht Club and his path to owning an NFT in the collection. We then use Bored Apes as a lens to understand how NFT projects are not just creating rare art but strong membership communities too. Beyond the cultural differences between NFT communities, it was fascinating to hear how projects are differentiating themselves with IP ownership, roadmaps, and DAOs. Please enjoy this breakdown of the Bored Ape Yacht Club.

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 Coinbase Prime, an integrated solution that provides an advanced trading platform, secure custody, and prime services so you can manage all your crypto assets in one place.

 

Coinbase Prime fully integrates crypto trading and custody on a single platform while giving clients the market's best all-in pricing through their proprietary Smart Order Router and algorithmic execution. Coinbase Prime extends beyond individuals - with companies like Tesla and Microstrategy using the investing platform to execute some of the largest trades in the industry. 

 

Coinbase is the only publicly-traded company with experience trading and custodying crypto assets at scale - build a unified investment portfolio with the most trusted name in crypto. Learn more by visiting coinbase.com/prime to get started.

 

-----

 

Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 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: @Web3Breakdowns | @patrick_oshag | @JoinColossus

 

Show Notes

 

[00:02:30] - [First question] - What the Bored Ape Yacht Club is

[00:03:39] - Motivations for owning a Bored Ape compared to traditional art 

[00:07:46] - The scope of prices, hierarchy, turnover, and trading overview of these NFTs

[00:09:51] - Distribution of rarity and why it matters 

[00:11:29] - How the project roadmap is managed by the member community

[00:16:23] - Who are the members and the key stewards of steering the ship

[00:18:08] - An example of a project where the owners don’t own the IP of their NFT

[00:20:56] - Underlying fundamentals and utility behind owning a Bored Ape 

[00:26:36] - Thoughts on fungible tokens inside of non-fungible projects

[00:29:06] - Ways to think about the value proposition of owning an Ape and an Ape token 

[00:30:36] - Different options for minting NFTs and their pros and cons

[00:34:36] - Literal mechanics of the minting process

[00:36:59] - Smart contract mediating of combining NFTs to generate rare ones

[00:39:20] - Building a bottom up brand and other examples of this trend

[00:41:50] - Are NFTs just gambling, or will they become investable assets like physical art

[00:46:09] - Blockchain infrastructure of the NFT space and whether it’ll stay on Ethereum

[00:48:48] - What makes the Bored Ape Yacht Club so innovative compared to other projects

Nov 18, 2021
Will Marshall - Indexing the Earth - [Invest Like the Best, EP. 251]
49:52

My guest today is Will Marshall, the co-founder and CEO of Planet. Will founded Planet in 2010 with a small team of NASA scientists to build a constellation of satellites that would image the entire Earth every day. Since then, Planet has successfully built and deployed 450 satellites into space, which the company is using to create a time series of images for every place on Earth.

 

Our conversation covers the untold space story. How space is going through an internet moment where cost reductions and performance enhancements have led to a seismic shift in what’s possible above our atmosphere, and how that can drastically improve life on Earth through unique datasets like the one Planet is piecing together.

 

Once you listen to Will speak about Planet’s progress and mission, it’s hard to think of a more underappreciated company in business today.

 

Please enjoy this great conversation with Will Marshall.

 

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 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.

 

------

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

------

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - His thoughts on the renaissance of the space industry

[00:05:09] - The earliest days of Planet and why he started the business

[00:09:22] - Unique data units captured by their satellites

[00:11:21] - What might we know in fifteen years using satellite data that we don’t today

[00:13:35] - The real estate of space and interesting angles to consider 

[00:15:59] - How customers interface with Planet and their early use cases

[00:20:57] - Thoughts on the sovereignty of space and the laws that exist currently  

[00:23:43] - Figuring out the dynamics and pricing of Planet’s business model

[00:27:34] - Examples of stress and tensions when working in space

[00:29:08] - The future of privacy and concerns we should have there collectively

[00:30:29] - Five different types of satellites and their functions

[00:31:39] - The most sci-fi potential futures that Planet may unlock someday

[00:32:54] - Indexing the Earth and using data to train machine learning algorithms

[00:34:02] - What he’s learned about Earth that is most surprising

[00:37:12] - Contributing factors to a 70% decline in life on the planet in 40 years

[00:38:35] - Ways that going public might impact Planet’s long term goals

[00:40:23] - The hardware story of building various prototypes of satellites

[00:42:18] - How much is built in house versus outsourced to fabricate their satellites

[00:43:48] - Complimentary space trends that are compounding beyond imagery

[00:45:32] - Whether or not they plan on making their data open-source

[00:47:15] - Democratizing their data and allowing other companies to build on top of it

[00:48:30] - The kindest thing anyone has ever done for him

Nov 16, 2021
Roelof Botha - Sequoia’s Crucible Moment - [Invest Like the Best, EP. 250]
01:07:32

My guest today is Roelof Botha, a partner at one of the world’s oldest and most successful venture firms, Sequoia Capital. A few days ago before I sat down with Roelof, he announced Sequoia’s boldest innovation since the firm was founded by Don Valentine in the early 1970s. Going forward, the firm will break from the traditional VC mould of fund cycles and instead restructure around a single, open-ended, permanent structure named The Sequoia Fund.

 

In our conversation, we first discuss the details of this change from all different angles and then dive into Roelof’s career. We talk about what’s changed over the past twenty years, his days at PayPal, what legendary investors he’s worked with have had in common, and what he’s learned from being involved in businesses like Square, YouTube, and Unity.

 

Please enjoy this great conversation with Roelof Botha.

 

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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At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

------

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - What led Sequoia to change their structure

[00:05:53] - Parallels between their approach and the problem Square set out to solve

[00:07:36] - The mechanics of the new fund and how it’ll affect their clients

[00:10:42] - How much discretion LPs will have when choosing to participate in sub-funds

[00:13:11] - What the future looks like and how public securities could be a dominant force

[00:15:02] - Benefits and value-unlocks that the new fund offers that weren’t available before

[00:16:55] - Comparing their structure to the current crossover funds we see emerging

[00:18:21] - What alignment looks like in this new structure for LPs

[00:22:02] - Cost of capital, interest rates, and their impacts on rates of return

[00:25:39] - Changes in the industry and founders that he’s noticed

[00:28:56] - What matters to him when meeting with young companies for the first time

[00:31:47] - The importance placed on value creation over value capture in the early days

[00:33:09] - Things that would dissuade him from partnering with a company

[00:34:18] - What the growth and leadership at Square has taught him over the years

[00:35:44] - Things he’s most excited about for payments looking forward

[00:37:34] - How often a company lowering friction with technology appeals to him 

[00:38:38] - Thoughts on Unity and its role in the growing trend of the metaverse

[00:40:28] - Why the open and decentralized nature of the future is so beneficial

[00:42:05] - Lessons learned about content and internet from working with YouTube

[00:44:08] - The landscape of developers today and MongoDB's role in it 

[00:45:24] - Commonalities between companies who have a successful second act

[00:48:16] - Good board members support founders during their pivotal moments

[00:49:26] - Learning to identify and hunt for crucible moments

[00:50:50] - Curiosity is the key ingredient of a great investor

[00:52:05] - What makes for a fantastic investment memo

[00:53:20] - The most memorable investment memo he’s ever read

[00:54:07] - Honing his leadership as his role has changed at Sequoia these past years

[00:55:51] - Thoughts on Sequoia’s brand and the scope of his ambition

[00:58:05] - What he’s most curious about in the world today

[00:58:46] - What technology wants most from people today

[01:01:13] - The difference between an accountant and an actuary's mindset and when each one is appropriate to inhabit

[01:02:38] - Differences between talent and genius 

[01:04:12] - Closing principals about business building he finds important to consider

[01:06:17] - The kindest thing anyone has ever done for him

Nov 05, 2021
Sarah Friar - Building the Local Graph - [Invest Like the Best, EP. 249]
01:13:26

My guest today is Sarah Friar, the CEO of Nextdoor, which connects people in local neighborhoods together. Sarah’s CV sparkles with impressive achievements at interesting businesses, and we spend a lot of time in this conversation thinking through what excellence looks like as a CEO, CFO, equity analyst, and board member. The rest of our discussion is focused on Nextdoor and how the soon-to-be public business is fostering connections between people and businesses in their local areas.

 

I do this podcast so I get to meet and learn from people like Sarah. I could have talked to her for hours. I hope you enjoy this great conversation with Sarah Friar as much as I did.

 

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.



------

 

At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick

 

------

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - What makes an excellent equity analyst

[00:05:51] - Things Sarah does differently as an operator because she was an investor

[00:08:29] - Key factors that make a great CFO

[00:09:31] - The role of the CFO in regards to capital allocation as a company grows

[00:11:50] - What convinced her to join Salesforce and Square

[00:14:45] - The initial spark and appeal that led her to join Nextdoor

[00:17:35] - Existing problems with ‘community’ and how they approach fixing them

[00:21:36] - Interesting and compelling data points about in-person interactions

[00:23:54] - Network density as a driving factor of product quality

[00:26:43] - What gives Nextdoor a unique angle against some of its existing competitors 

[00:28:51] - Thoughts on platform leakage and user retention

[00:30:57] - Successful strategies for deploying Nextdoor in a new country

[00:35:32] - Having a feed and trying to avoid creating echo chambers

[00:37:04] - Some of the biggest mistakes they’ve made while trying to grow

[00:38:49] - Options for a business model and thoughts on advertising 

[00:43:25] - The importance of scale, advertising, and their relationship dynamic

[00:45:55] - Ways she’s learned to effectively steer the businesses strategy

[00:49:48] - Why she doesn’t like titles 

[00:51:07] - Key levers that will allow Nextdoor to succeed in the future

[00:53:35] - How advertisers evaluate platforms like Nextdoor compared to Google or Facebook

[00:57:19] - What a successful board member looks like and how she’s learned to be one

[00:59:34] - Leading with transparency and empathy

[01:02:00] - An overview of what Ladies Who Launch is and what they do

[01:03:57] - Way to educate our children about finance and encourage financial literacy

[01:07:51] - Making your platforms welcoming and guiding users away from conflict

[01:10:30] - The kindest thing anyone has ever done for her 

Nov 02, 2021
Universal Music Group: The Gatekeepers of Music - [Business Breakdowns, EP. 32]
01:16:19

Today, we are running a special episode of Business Breakdowns on our Invest Like the Best feed. When we launched Breakdowns, we hoped to cover industries and businesses that we were “well known but poorly understood.” This deep-dive on UMG and the music industry is just that - you will walk away with a whole new appreciation for artists, labels, and what streaming technology has done for a historic industry. If you enjoy this episode, please be sure to subscribe on your preferred podcast player and check out our growing catalog of episodes.

 

Today we’re breaking down Universal Music Group. As one of the largest music businesses in the world, UMG is home to many of the world’s greatest artists, including Taylor Swift, U2, and The Beatles catalog. A discussion on UMG requires a deep dive into the history of music itself, how it was historically monetized, the shift from physical to digital, and what streaming has meant for the various pieces of the ecosystem. Our guest, Arman Gokgol-Kline, a partner and investor at Ruane, Cunniff & Goldfarb, walks us through that evolution of the music industry before we dive in on UMG.

 

In our discussion, we first break down the industry pre and post Napster, looking at the ways music was sold historically, and how that led to both record profits and a consumer revolution. We then assess streaming’s impact on the industry and how, contrary to what you might think, labels may be more important in a marketplace where it’s easier than ever for creators to record and release music. Finally, we finish with UMG’s place in the ecosystem. The primary drivers of the business, how they’re able to attract the world’s superstars, and how they think about deploying dollars to acquire new artists and timeless catalogs.

 

Please enjoy this fantastic breakdown of Universal Music Group.

 

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 Quartr. With Quartr, you can access conference calls, investor presentations, transcripts, and earnings reports – straight from your pocket. Quartr is 100% free and includes companies from 12 markets including the US, the UK, Canada, India, and all the Scandinavian countries. Quartr is available for both iOS and Android, so check out the app today.

 

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This episode is brought to you by Brex. Brex began as the first corporate card for startups and now offers a full financial stack built for scale. Get 10-20x higher credit limits, uncapped rewards, easy deposits and payments, and expense management all in one. Grow your business faster with Brex.

 

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Business Breakdowns is a property of Colossus, LLC. 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

[00:04:01] - [First question] - How technology disrupted the music business and it’s evolving history

[00:12:44] - What the industry of music labels looks like from the 90s to today

[00:21:19] - How it feels as a high-tier artist to engage with a label directly today

[00:28:20] - The revenue and business model of an artist akin to Taylor Swift

[00:30:44] - The differences between UMG's main sources of revenue; music publishing and recording

[00:35:08] - General margins and trends for music publishing

[00:36:22] - Ownership and mechanics of monetizing an artist’s Intellectual Property 

[00:40:57] - How streaming revenues are divided among stakeholders

[00:46:23] - History of the bargaining power of labels and streaming platforms

[00:51:25] - Capital allocation, ROI, and acquiring IP and catalogs

[00:57:39] - Thoughts on the growth profile of the industry as an investor

[01:02:23] - Potential risks to UMG in emerging technology and new creator trends 

[01:08:50] - Reasons why an artist would pick UMG over other major labels

[01:12:42] - Diversity and how artists are sometimes treated by labels

[01:14:02] - A growing increase in music consumption across the world

Oct 28, 2021
Alex Rampell - Investing in Operating Systems - [Invest Like the Best, EP. 248]
01:17:31

My guest today is Alex Rampell, General Partner at Andreessen Horowitz. Alex has a long history in fintech, having co-founded six companies in his career, including Affirm and TrialPay. During our conversation, we cover Alex’s framework for positive selection in investing, why the best investments are often operating systems or systems of record, and Alex’s views on the future of fintech. For those that have listened to our Business Breakdown on Visa with Alex - you know the intellectual horsepower he brings to every discussion. This conversation is no exception. 

 

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 20,000 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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 

 

------

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - Lean into positive selection and avoid adverse selection

[00:07:48] - Thoughts on growing capital formation in private markets

[00:14:01] - Why it’s useful for investors to think in terms of bonds and call options instead of equity

[00:18:39] - Doing more with less and hunting for operating systems to invest in

[00:28:08] - His views on infrastructure and the presentation layer conundrum

[00:33:32] - The sequencing involved in building an operating system over time

[00:40:11] - Rise of the creator class and the coming tailwind post-cloud technology; the rise of the solopreneur 

[00:43:32] - The pig joke and his thoughts on the FinTech space

[00:47:47] - Big financial services functions that will be embedded in non-financial businesses

[00:51:07] - Deciding which functions and financial services models are most attractive

[00:57:01] - What a shift towards data and FinTech might unlock for the world writ large

[01:02:40] - How to improve payment profits by reducing credit rates

[01:04:12] - The threat that Buy-Now-Pay-Later companies pose to Visa and Mastercard

[01:12:17] - How the struggle between distribution and innovation continues to change

[01:15:04] - The kindest thing that anyone has ever done for him 

Oct 26, 2021
Sam Bankman-Fried - Creating a Perfect Market - [Invest Like the Best, EP. 247]
01:14:56

My guest today is Sam Bankman-Fried, founder and CEO of leading cryptocurrency exchange, FTX. In a little over two years, FTX has registered 1.2 million users, grown to facilitate $10.9 billion of daily trading volume, and reached an $18 billion valuation. Prior to FTX, Sam worked at Jane Street Capital before founding a quant trading firm of his own, Alameda Research. At just 29, Sam has packed a lot into a short period of time, and as I’m sure you’ll hear, he has a special ability to harness uncertainty and think deeply across a range of topics.

 

In our discussion, we cover the building blocks of a perfect market, the key areas of inefficiency in today’s exchanges, and Sam’s north stars of product design and effective altruism. We also talk about fairness in crypto markets, how FTX thinks about user acquisition, and derivatives as key enablers of properly functioning markets.

 

Please enjoy my great conversation with Sam Bankman-Fried.

 

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 20,000 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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 



------

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:57] - [First question] - What motivates him and what the true north of his vision is

[00:07:12] - Evaluating the impact of well-functioning markets and philanthropic spending

[00:11:55] - The key functions and building blocks of a perfect market

[00:14:59] - Who pays $50 million to access fiat market order books

[00:21:49] - What is valuable about having access to order book data

[00:25:41] - Assessing and understanding the state of fairness in crypto markets today

[00:31:51] - Can crypto only move as fast as the fiat system keeps up

[00:32:43] - The advantages and disadvantages of stablecoins and USDT

[00:34:46] - How much fiat inflow there is into crypto markets and exchanges today 

[00:37:36] - What it is about cryptocurrency exchanges that are so appealing to him 

[00:42:21] - Building in a dynamic world and deciding the sequence of problems to solve

[00:45:12] - Whether or not the US is on the wrong side of crypto and countries competing for healthy regulatory environments in this emerging asset class

[00:47:25] - Thoughts on centralization and what being decentralized unlocks

[00:50:22] - Why derivatives are such a key function of properly functioning markets

[00:52:38] - The competitive landscape between derivatives and exchanges

[00:54:35] - Spending marketing dollars and paid acquisitions for FTX

[00:57:30] - The growing trend of user-generated content becoming user-generated assets 

[01:02:24] - How many layer one blockchains we’ll need and the competition for dominance

[01:05:18] - Thoughts on Bitcoin as the pioneer of the space and how relevant it still is

[01:06:26] - Possibly reaching a state where everything happens on-chain

[01:08:23] - What he means when he says he has more RAM than hard drive space

[01:09:39] - Amassing wealth insanely fast and whether or not it affects him

[01:10:26] - Important things to consider in this rapidly growing space

[01:12:02] - A decision he made while respecting the power laws that govern us

[01:13:10] - The kindest thing anyone has ever done for him

Oct 19, 2021
Nick Neuman - Becoming Your Own Bank - [Invest Like the Best, EP. 246]
01:03:57

My guest today is Nick Neuman, CEO and co-founder of Casa. Casa helps bitcoin investors and owners keep their digital assets safe from loss or theft by providing managed self-custody services. In our discussion, we cover the history of asset custody from ancient temples to decentralized ledgers, look at the mechanics of how private keys work, and explore why people are better off holding the keys themselves. We then dive into the future of digital wallets as gateways into our virtual lives, what’s interesting about identity authentication more broadly, and whether these innovations may lead to unintended consequences. Please enjoy this great conversation with Nick Neuman.

 

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 20,000 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 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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:23] - [First question] - The history of asset custody

[00:07:56] - What private keys are and their role in financial security 

[00:12:21] - Overview of storing a token in a wallet and accessing with a private key 

[00:15:28] - Thoughts on private keys through the lenses of convenience and safety

[00:18:49] - Solving both self-custody of assets and peace of mind

[00:21:39] - How the user experience will feel once self-custody is properly developed

[00:24:11] - Why asset custody is so interesting and what a perfect scenario unlocks

[00:27:05] - Is the DeFi ecosystem an early manifestation of a self-custody financial system 

[00:28:57] - Ways Casa is planning to become a convenient and diverse platform for users

[00:32:16] - The role wallets will play in the future of a digital world

[00:34:56] - Forms of authentication that are most appealing in creating a seamless user experience

[00:37:39] - Overview of what hardware wallets are and how they work

[00:40:17] - Different security options that Casa offers from the simplest to the most secure

[00:44:51] - How many crypto holders there are and how many use self-custody

[00:47:31] - The craziest security set up around Bitcoin he’s ever heard of 

[00:48:49] - What the most ideal outcome for Casa looks like in the coming decade 

[00:51:26] - Thoughts on the competitive landscape and potential growth challenges 

[00:53:07] - Important aspects of the crypto ecosystem other than security  

[00:55:49] - How empowered people feel when they successfully adopt self-custody

[00:57:13] - Whether or not there are ways that the current centralized system is more secure

[00:59:58] - Thoughts on offering a way for users to display they are protected by Casa 

[01:01:31] - The kindest thing anyone has ever done for him

 

Oct 12, 2021
Devin Finzer - An Everything Store for Digital Assets - [Founder’s Field Guide, EP. 53]
50:58

My guest today is Devin Finzer, co-founder and CEO of OpenSea, the world’s largest NFT marketplace. In a journey that started like many other founders in the space, Devin went deep down the crypto rabbit hole in 2017 and became particularly fascinated with the potential behind digital assets.

During our conversation, we touch on the origin story of OpenSea, how Devin differentiates between the spectrum of NFTs in the market, and what he sees as the opportunity in the future for the industry. We also talk about the various risks within a blockchain, from security dynamics to market speculation. I hope you enjoy this great conversation with Devin Finzer.

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 Robinhood, Marqeta, 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".

 

-----

 

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

[00:02:56] - [First question] - When he first thought up the genesis of OpenSea

[00:06:00] - What is listed on OpenSea, assets and volume, and the scope of the platform

[00:07:26] - Thoughts on potentially becoming the current era “everything store”

[00:09:22] - How they managed to become the main NFT trading platform

[00:12:28] - What NFTs are, their various classes, and ways they’re stored on the blockchain

[00:15:25] - How much transaction and auction volume happens on-chain

[00:17:07] - Profile picture style NFTs and what’s exciting about them

[00:19:24] - ArtBlocks and the mass interest in AI-generated art

[00:21:22] - What he’s learned and seen about the emerging crypto gaming space

[00:24:38] - The user experience of buying an NFT on OpenSea

[00:26:45] - How the ownership transfer works between wallets

[00:28:04] - Whether or not they have plans to partner with other companies

[00:30:32] - How they think about what gets placed on OpenSea and why

[00:32:09] - Thoughts on take rate and their 2.5% take rate of transactions

[00:33:22] - Why their take rate is so low compared to other sale platforms online

[00:34:47] - OpenSea’s relationship with the Ethereum blockchain and other integrations

[00:36:50] - Perspective on wallets both as businesses and products

[00:39:16] - Potential risks and the dark side of the unregulated NFT space

[00:40:48] - The massive boom and bust cycles of crypto and the high prices of NFTs

[00:41:59] - Interesting areas of Web3 that are in development today

[00:44:19] - The project he’s enjoyed watching grow the most in the crypto world

[00:46:42] - What OpenSea might look like in the future if the best-case proves true

[00:48:59] - The kindest thing that anyone has ever done for him

Oct 07, 2021
Jenny Lefcourt - The Go-to-Market Motion - [Invest Like the Best, EP. 245]
01:01:32

My guest today is Jenny Lefcourt, an equal General Partner at seed-stage venture firm Freestyle Capital, where she manages $450 million in seed investments. Jenny has been engrained in the tech world since the early days of the internet. She dropped out of her Stanford MBA program to co-found online wedding registry startup WeddingChannel.com with classmate, Jessica Herrin, which was subsequently acquired by The Knot. During our conversation, we cover Jenny's investment frameworks, why she believes a deep understanding of the customer is key for founder success, and what makes great go-to-market strategies. We also touch on some of Jenny's favorite market themes around technology for the aging population, the future of work, and the growing low-code/no-code market. Please enjoy my conversation with Jenny Lefcourt.

 

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 20,000 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 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".

 

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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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - Her background and some formative experiences that lead her to where she is today

[00:08:38] - Common patterns of desirable founders when it comes to customer focus

[00:09:50] - Her investing framework for evaluating and deciding which companies to invest in

[00:12:32] - Innovation and adoption in the technology sector for the older generation

[00:15:11] - The biggest jobs to be done in this space currently today

[00:17:33] - Cultural differences in how the West views and treats their elderly

[00:21:02] - Business model options for turn-key apartments offered by UpsideHoM

[00:22:48] - Other categories and potential opportunities in tech geared towards the elderly

[00:24:59] - What you need to do differently when building products for the elderly

[00:27:32] - How she learns about a new prospect’s go-to-market approach and reverse engineering an action plan to execute it

[00:32:03] - Founders, You Want to Sell Viagra

[00:33:33] - Selling transformation and an overview of this idea with BetterUp

[00:36:30] - Her thoughts on how the world and the future of work might change 

[00:41:14] - Interesting approaches to improving the onboarding and recruiting process

[00:43:24] - The emerging movement of low code/no code tools

[00:46:58] - How she as an investor adjusts as the world becomes more digitally connected

[00:49:02] - Ways her life has most dramatically changed over the past few years

[00:51:33] - Lessons learned from her time at All Raise

[00:53:40] - Outstanding and remaining barriers to inclusive and diverse teams

[00:58:47] - The kindest thing anyone has ever done for her

Oct 05, 2021
Dave Girouard - Making Better Loans - [Founder’s Field Guide, EP. 52]
01:07:05

My guest today is Dave Girouard, co-founder and CEO of Upstart, a lending platform that leverages AI to make loans more accessible and affordable. Dave started in Silicon Valley as a Product Manager at Apple and later spent eight years at Google, where he built their suite of cloud apps. In our discussion, we cover the lessons Dave has learned about building speed into a habit, the intricacies of training an AI model to predict the future, and what it was like to start a fintech business as an outsider. We also discuss the past, present, and future of lending, why Dave and his team have no plans to build a super app and the differences between public and private market investors from a founder’s perspective. One of the tropes you hear these days is that lending has become a customer acquisition tool for FinTechs, but as Dave explains, the market and opportunity set in lending itself should not be underestimated. Please enjoy this great conversation with Dave Girouard.

 

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 brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.

 

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This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.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

[00:02:54] - [First question] - Lessons learned about adopting speed as a habit

[00:05:39] - Knowing which decisions require your attention and are worth it as a CEO

[00:07:00] - What slows down decision-making execution and overcoming it

[00:09:34] - Ways to persuade partners to move as fast as you do

[00:10:44] - One of his most valuable lessons learned from his time at Google

[00:12:20] - The key insight that first lead him to the idea of creating Upstart

[00:15:10] - The early days of learning about the financial lending space

[00:16:49] - Figuring out how to improve on an age-old rigid and regulated system 

[00:18:42] - Credits scores, what drives them, and why they’re suboptimal

[00:20:57] - Overview of building an AI learning model and applying it to loans

[00:23:24] - Surprising findings on predictions and evaluating loan applicants

[00:25:16] - Machine learning algorithms and interwoven programmer bias

[00:26:49] - The role interest rates play in their business model

[00:28:34] - Revenue model and transactions that fund Upstart 

[00:31:43] - Who the typical customer is and their user experience

[00:33:09] - Ways in which they can compound their AI models for other services

[00:35:10] - The biggest hurdle encountered when building Upstart

[00:36:55] - How he’s seen the FinTech space in his area change over time

[00:38:39] - A pie chart on revenue for financial services today

[00:40:24] - Why there are more profits in lending than payments 

[00:41:25] - Major loans types and how they might change in the future

[00:44:12] - Disruptive aspects of the buy now pay later consumer movement

[00:46:09] - How much Upstart could change the future of lending over a decade

[00:48:17] - Inefficiencies of the lending space that still exist today

[00:49:43] - The most important decisions he’s made while building Upstart

[00:51:59] - Things to know when building a business that sells to banks

[00:52:49] - How it feels to interact with hired CEOs versus founder CEOs

[00:55:05] - Thoughts on cryptocurrency and AI writ large

[00:57:00] - Areas that have his attention and get him excited lately in FinTech

[00:58:58] - State of the art AI growth and what lingers over the horizon

[01:00:36] - What he’s learned about being a public market CEO versus a private one

[01:02:38] - Differences between public market and private market investor philosophies

[01:03:53] - Major battle scars from raising capital for Upstart

[01:05:12] - The kindest thing anyone has ever done for him

Sep 30, 2021
Jay Hoag - Calibrating Market Adoption - [Invest Like the Best, EP. 244]
01:15:50
My guest today is Jay Hoag, co-founder of TCV. If you look at Jay’s investment track record, it’s a “who’s who” of tech giants with Airbnb, Netflix, Peloton, Zillow, and a list that does not stop there. Needless to say, Jay has a Hall of Fame career. During our conversation, we talk about his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors. Jay has such a wealth of experience that is on display throughout this episode. Please enjoy my conversation with Jay Hoag.

 

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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com

 

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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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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

[00:03:13] - [First question] - Some of his early key formative experiences that shaped his worldview as an investor

[00:06:29] - How much software businesses have changed since he started investing in them

[00:08:28] - The key insight that led him to create TCV

[00:11:36] - Generating returns by swinging less and raising your average

[00:15:06] - Understanding and evaluating a value proposition in its early stages

[00:22:08] - What slightly crazy founders look like and why it’s important for a company

[00:25:47] - Whether or not we’re in the golden age of content already 

[00:28:27] - Why Peloton was rejected so many times before TCV invested in them

[00:32:32] - Things founders often need from him and how he helps them succeed

[00:36:15] - Lessons learned from investing in public markets versus private ones

[00:41:35] - Advice for founders when it comes to conveying their ideas to investors

[00:44:55] - The social dimension of interactive and network building content

[00:46:18] - How important maintaining a focus in the early days is for a new company

[00:48:07] - The most challenging aspect of executing his strategy today

[00:50:48] - One of the most emotionally stressful episodes while launching TCV

[00:53:44] - Supporting your founders during the good and tough times

[00:55:16] - New potential headwinds and tailwinds in the tech space writ large

[00:59:14] - Things people might be overlooking today that could be great opportunities later

[01:02:58] - Whether or not internet companies are threatened by the crypto boom

[01:04:32] - What most has him most excited about the world today

[01:06:20] - Advice for company building in the investing world in general 

[01:09:48] - The kindest thing anyone has ever done for him



Sep 28, 2021
Gina Bianchini - Helping Creators Build Communities - [Founder’s Field Guide, EP. 51]
55:35

My guest today is Gina Bianchini, founder and CEO of Mighty Networks, which gives creators a platform to start, grow and own their social communities.

 

In our conversation, we cover the differences between leadership and management, the lessons Gina learned building a similar business in the 2000s with Marc Andreessen, and the elements that make up a thriving community. We talk about community design, finding ways to connect like-minded people, why it’s so important to create movement, and what the future may hold for creators.

 

Please enjoy this great conversation with Gina Bianchini.

 

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 brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.

 

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This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.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

[00:02:35] - [First question] - A period in Gina’s career of deep intensity that she learned from

[00:04:28] - Solving ways to preserve her energy as a high performing entrepreneur

[00:08:19] - How much of her day is spent doing things she wants to do 

[00:11:24] - What is unique to leadership that differs from management

[00:14:49] - The insight that led to what eventually became Mighty Networks

[00:27:19] - Enabling features of a community that Mighty Networks offers creators 

[00:31:51] - Key symptoms of a healthy online community

[00:37:35] - Differences between their emerging communities and the power of belonging

[00:41:38] - Turning movement and accomplishment into a software platform

[00:47:32] - Tying passion into purpose and the structure of a movement

[00:50:20] - The biggest potential risks and challenges that Mighty Networks faces

[00:52:56] - The kindest thing anyone has ever done for Gina 

Sep 23, 2021
David Fialkow - Paint Outside the Lines - [Invest Like the Best, EP. 243]
01:03:35

My guest today is David Fialkow, co-founder of General Catalyst. If you are looking for a dose of fun, charismatic energy from a very unique investor then this is the conversation for you. David has a diverse background not only as an investor but also as a philanthropist and filmmaker. He won an Academy Award for his role as the producer of the 2018 documentary Icarus. During our conversation, David and I dive into what makes a great founder, the importance of storytelling, and the value of effectively convening people within your network. After listening to all of his great stories, I think you’ll see why David has so much fun and success helping founders. Please enjoy my great conversation with David Fialkow.

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

 

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] - How the process started that led to filming Icarus and becoming a VC 

[00:16:01] - Lessons learned about identifying creativity in potential founders

[00:19:26] - What it looks like when a founder doesn’t clearly love their product 

[00:24:35] - Different aspects of building a successful investment firm

[00:28:22] - Features of Ken Chenault that differentiates him from other CEOs

[00:30:12] - Applicable lessons for the effective convening of people

[00:35:20] - Whether or not he cares about the business model of new companies they back 

[00:40:57] - The story of Icarus

[00:47:24] - What is David drawn to at the moment

[00:51:13] - Key ingredients required to tell a powerful and convincing story

[00:53:16] - The kindest thing anyone has ever done for him

Sep 21, 2021
Justin Waldron - The Future of Social Gaming - [Founder’s Field Guide, EP. 50]
01:03:05

My guest today is Justin Waldron, co-founder and President of Playco. Justin is a pioneer of the social gaming industry after he co-founded Zynga at age 19, and he has continued to build games ever since. In our conversation, we cover how Justin sees the future of gaming as social platforms evolve, how gaming may be the next tool for content creation, and how Playco has approached aligning incentives for game creators and players. As talk of the metaverse becomes more mainstream, it’s fascinating to hear directly from those around it. I hope you enjoy my conversation with Justin Waldron.

 

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 brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.



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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

[00:02:47] - [First question] - His thoughts on the metaverse and why it’s so interesting

[00:06:07] - The ways hardware and software will shape the future of digital worlds

[00:08:23] - Examples of how these digital experiences might look in the years to come

[00:10:45] - His background, history, and his life before founding Playco

[00:16:31] - Ways content creates human interactions and its role in user retention

[00:18:43] - How successful social media platforms encourage user interaction 

[00:20:51] - Games becoming a way to create content and being a creation tool

[00:23:06] - This history of user-generated content for pre-existing games

[00:27:32] - Defining what instant gaming is and how it’s different from traditional gaming

[00:30:24] - The technological problems and hurdles in creating games that load instantly

[00:34:00] - Parallels between instant gaming and cloud-powered processing

[00:36:43] - What types of games are most desirable for games shared via links

[00:38:58] - The feel of this model working in real-time and the project that’s furthest along

[00:41:37] - Lessons learned about working with and structuring partnerships with social media and content creation giants

[00:45:06] - Ways in which social network platforms are evolving

[00:48:04] - Playco’s business model and smart approaches to generating revenue

[00:50:28] - The role NFTs might play in instant gaming and making crypto mainstream

[00:53:03] - Crypto wallets and building one in house versus using a 3rd party wallet

[00:54:17] - What the best case scenario will look like for Playco in a decade from now

[01:00:44] - Other companies to go check out that leverage and empower individuals 

Sep 16, 2021
Daniel Ek - Enabling Creators Everywhere - [Invest Like the Best, EP. 242]
01:26:26

Today is a special episode because it marks five years since I released the first episode of Invest Like the Best. Over those years, I’ve learned so much from so many investors and builders, but today’s guest may have taught me the most.

 

Daniel Ek is the CEO and founder of Spotify, and I find him to be one of the most thoughtful business leaders in the world. Daniel is the perfect guest for this special occasion because he exemplifies the curiosity, humility, leadership, and dogged determination that I think characterizes the best investors and operators.

 

In our conversation, we discuss the differences between the world of bits and atoms, how Daniel gets up to speed in challenging new fields, and why Europe might be a sleeping giant about to wake. We then bring the discussion back to Spotify, the evolving creator ecosystem, and Daniel’s frameworks for leading the business into its next chapter of growth.

 

Over the past 5 years, we’ve produced more than 300 of these shows and reached nearly 30 million people. I am deeply thankful to the guests who’ve been willing to share their knowledge with us all and even more thankful to everyone who has taken the time to listen and learn alongside me. This has truly been the greatest pleasure of my career, and I don’t plan on ever stopping this journey.

 

Now, Please enjoy my conversation with a great friend, Daniel Ek.

 

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.

 

------

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, and Ben Thompson.

 

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

[00:03:37] - [First question] - Building atoms versus bits and if we’re destined to return to atoms

[00:08:04] - What makes early-stage atoms companies more challenging to build

[00:10:20] - Whether or not we’re starting to see cross-pollinating of infrastructure companies into other sectors

[00:13:00] - His process for learning about new fields when he knows nothing

[00:16:12] - Big and interesting problems that we will need to solve 

[00:19:35] - The nature of healthcare’s technological adoption compared to other sectors

[00:24:13] - Downstream unlocks of collecting and observing big pools of data

[00:30:00] - What he has found effective about taking an idea from 0 to 1 

[00:33:40] - Lessons learned about compounding change and staying patient

[00:37:17] - History of European technology and its unique regional characteristics

[00:42:40] - Cultural and continental traits that may make Europe a technological leader 

[00:45:42] - Characterizing the major lessons learned from his time at Spotify 

[00:50:31] - How artists are changing the ways they connect with their fans via Spotify

[00:55:44] - What he would change about the legacy music industry given today’s tools

[01:00:15] - The influence global exposure has on internet companies and creatives 

[01:03:02] - Interesting observations about the recent explosion of podcast popularity

[01:07:36] - Working with, carrying, spreading, and maintaining Spotify’s sacred source

[01:12:37] - Ways we can improve and sharpen our decision-making skills

Sep 14, 2021
Gabby Dizon - Mapping the Metaverse Economy - [Founder’s Field Guide, EP. 49]
56:46

My guest today is Gabby Dizon, co-founder of Yield Guild Games or YGG. In 2020, Gabby and his co-founders built YGG around the growing “play-to-earn” economy within blockchain-based games. Based in the Philippines, YGG effectively backs players - who might not otherwise be able to afford to play - in exchange for a share of their profits. Today, YGG is paying out over a $1mn US dollars a week to players within its community - largely concentrated in their home country of the Philippines.

 

The play-to-earn model has seen its most rapid growth in the popular NFT-based game “Axie Infinity”. Players earn tokens within the game which can be exchanged into local currencies or be used to purchase more digital assets. For a sense of how this market has expanded, Axie Infinity has already reported over $1.5bn in sales over its history- and nearly $900mn over the last 30 days.

 

The speed at which these games and the ecosystems around them are growing is remarkable. In our conversation, Gabby explains YGG’s decentralized structure, the unit economics of their business model, and how he deals with the volatility of crypto assets when trying to build a durable, long-term business. We also discuss the broader metaverse landscape, how it might evolve, what might derail it, and the technicalities of building a token-based, as opposed to equity-based, business.

 

I hope you enjoy this wild conversation with Gabby Dizon.

 

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 brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.

 

-----

 

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

 

-----

 

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

[00:03:34] - [First question] - What Yield Guild Games is and what they do

[00:04:30] - The growing popularity of play-to-earn games in the metaverse 

[00:06:07] - Major categories of digital assets that exist today 

[00:08:11] - How players can earn money playing Axie Infinity

[00:10:47] - The business model of YGG and what they offer to players

[00:12:42] - Potential earnings of playing Axie Infinity

[00:15:03] - Possible risks to demand and what the Axie economy could be in a few years

[00:17:54] - Evaluating games that are worth investing in

[00:19:55] - The kinds of things that will be most valuable across games in the future

[00:21:37] - Differences in value between cosmetic and utilitarian in-game purchases

[00:23:04] - Key focuses of YGG over the near future

[00:24:47] - What’s different about labor and capital in the metaverse

[00:27:11] - How tokenomics works and value grows for a DAO

[00:29:02] - Ways DAOs are better or worse than traditional equity tables

[00:30:11] - The state of YGGs economics today

[00:31:16] - The Guild’s player retention and growing their scholars

[00:32:54] - Barriers to entry for building a competitive DAO like YGG

[00:34:14] - What made Gabby so interested in crypto originally

[00:36:38] - His personal journey to crypto games

[00:37:53] - Jobs that may carry over from the real world into the metaverse

[00:39:36] - Companies that will arise focusing solely on in-game item creation

[00:41:18] - Base layers of infrastructure needed to create the best future for crypto gaming

[00:44:32] - Shared qualities between games that have a high replayability rate

[00:46:40] - Good and bad tokenomic ecosystem designs

[00:48:17] - What the biggest risks are for the future success of crypto gaming  

[00:49:26] - What factors will ensure the future growth and adoption of crypto gaming  

[00:50:25] - How much fiat flows through Axie and the growing value of in-game assets

[00:52:05] - Whether or not we’ll see purchasable utility items in the future

[00:53:21] - What he’s most excited about for the future of the metaverse

[00:54:52] - The kindest thing that anyone has ever done for him

Sep 02, 2021
Scott Malpass - Building a Great Endowment - [Invest Like the Best, EP. 241]
01:02:05

My guest today is Scott Malpass. Scott was the CIO of Notre Dame's endowment for 32 years and has always been a pioneer at the forefront of the endowment investing world - leading Notre Dame's early investments into Sequoia as well as some of the premier fund managers in China decades ago. Scott built the endowment into a powerhouse, scaling it from $400 million to over $12 billion of assets under management across 175 managers. In our conversation, we talk about the qualities he looks for in great investors, how asset classes have evolved over his 30 years of investing, and how Scott recruited top talent to work at Notre Dame’s endowment. Scott is clearly on the Mt. Rushmore of institutional investors, and I’m lucky to consider him a mentor and a friend. I hope you enjoy this great conversation with Scott Malpass.



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 20,000 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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 

 

------

 

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

[00:03:54] - [First question] - Finding his way to investing and Notre Dame

[00:06:11] - Key milestones of running their endowment for so long

[00:07:58] - What an endowment model is and how it’s evolved

[00:10:30] - The ingredients that unite their shared successes

[00:11:46] - His philosophy on building a differentiated investing team

[00:13:11] - How he approached talent identification when hiring new managers

[00:15:39] - The importance of understanding who someone was before they became an investor

[00:17:12] - Episode: Steve Mandel, Investing Behind Change

[00:17:28] - Whether or not someone has a reliable and solid core

[00:19:03] - Differentiating between self-confidence and an over-inflated ego

[00:20:27] - Evaluating real investing skills in an individual

[00:21:44] - The most memorable major early partner he brought on to the endowment

[00:23:14] - What made Don Valentine and Sequoia so special

[00:24:21] - Forcing good long-term incentive alignment with a firm

[00:26:35] - What makes a GP exceptional in how they treat LPs

[00:28:01] - How many managers actually have the ability to create alpha

[00:29:24] - His thoughts on venture capital and how he’s seen it evolve

[00:32:40] - The role private equity played in his success and how it’s changed over the years

[00:34:36] - Why diversify when managing such a large pool of capital

[00:35:58] - Public equity as an area of opportunity relative to private and venture capital

[00:38:08] - Bonds in an endowment and high net worth family offices

[00:39:32] - Whether or not equities are still appealing

[00:40:20] - Lessons from investing in China so early in his career 

[00:42:59] - What he’s learned about effective leadership from leading the team at Notre Dame

[00:44:54] - Advice on building your own basic portfolio

[00:47:03] - Portable classroom lessons that lend themselves to effective teaching

[00:48:28] - Why it’s important to do team-building exercises and off-sites

[00:50:07] - His thoughts on cryptocurrency and how others should think about it

[00:51:52] - Students that he’s most proud of across his career

[00:54:56] - Ways you should spend your 20s if you want to become a great investor

[00:55:49] - What’s on the horizon for him over the coming years

[00:57:55] - The kindest thing anyone has ever done for him

 

Aug 31, 2021
Mike Maples, Jr. - A Playbook for Startups - [Founder’s Field Guide, EP. 48]
01:05:26

My guest today is Mike Maples, co-founder and partner of Floodgate. As a child of the computer revolution, Mike was deconstructing calculators in grade school, writing video games in high school, and inevitably found himself building businesses in Silicon Valley after college. After his success as an operator, Mike eventually transitioned to become a full-time venture investor in the 2000s, and has since built a track record that includes Twitter, Twitch, Lyft, Octa, and a long list of successful tech businesses.

 

I'm not sure I've recorded a conversation with more applicable ideas and advice for company builders. We discussed early insights and secrets, value hypothesis testing, customer development, growth, team orchestration, and a lot more.

 

This is a masterclass from somebody who has seen it all. Also, do not miss his answer to the kindest thing question at the end of the conversation. I hope you enjoy this great talk with Mike Maples.

 

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

-----

 

This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. Learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

 

-----

 

This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambiguous problem, then Versett is the firm to call. To check them out, visit versett.com/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

[00:03:08] - [First question] - His philosophy on the power of forcing a choice

[00:04:43] - How he knows when he comes across a team that has an apple quality

[00:07:39] - Exploring and hunting new inflections in ever-changing systems

[00:10:37] - Why recognizing winning insights allows you to not have to predict the future

[00:12:23] - Whether or not the evolving nature of the funding landscape changes his thinking

[00:14:18] - An example of his insight framework and stress testing a team’s potential

[00:17:21] - Practice reckless optimism

[00:18:54] - Commonalities between teams and their ideas when they get inflections wrong 

[00:20:12] - What the value hypothesis is and how to test it

[00:22:15] - Ways that effective startup teams operate compared to big corporations 

[00:25:36] - His involvement post-investment and where outsiders can be most helpful in a companies’ early days

[00:28:34] - Lessons learned about finding, convincing, and marketing to their first customers 

[00:32:13] - An example of early customer selection done phenomenally well

[00:34:09] - Why it was possible for companies like Justin.TV and Lift to pivot so dramatically from their original ideas 

[00:38:49] - Customer development and using good customers to your advantage

[00:42:31] - Who went from founder to the best growth executive 

[00:43:05] - What he thinks his firm will need to do to continue offering an apple to founders

[00:46:08] - The most useful stress tests his firm can offer founders

[00:46:52] - Defining category design and what the process of category design looks like

[00:50:33] - Inflections he’s currently paying the most attention to

[00:52:07] - His experience with an HP35 calculator and how it shaped his life 

[00:54:41] - What venture capital may look like in the future

[00:56:30] - The most difficult things he faces in his career

[00:57:52] - Ways he’s learned to manage failure more effectively

[00:59:06] - The kindest thing that anyone has ever done for him

 

Aug 26, 2021
Renata Quintini and Roseanne Wincek - Investing at the Supercritical Stage - [Invest Like the Best, EP. 240]
01:01:47

My guests today are Renata Quintini and Roseanne Wincek, co-founders and managing directors of Renegade Partners. Before launching Renegade, Renata and Roseanne were partners at high-profile VC firms, Lux Capital and IVP. 

 

During our conversation, we explore their careers and what led them to launch Renegade. We cover what it means to invest at the “Supercritical Stage” in venture and dive into a variety of topics around this theme. We then discuss their investing philosophies more broadly, covering what best-in-class talent pipelines look like, what quality revenue means to them, and what worries them most in search of businesses with outsized potential returns. I think this episode highlights that even as competition in venture has intensified - the best VC partners can offer more than just capital.  I hope you enjoy my conversation with Renata and Roseanne.

 

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 20,000 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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 

 

------

 

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

[00:03:57] - [First question] - What the process of starting a new investment firm was like

[00:05:22] - Why the world needs another venture firm

[00:06:48] - The biggest takeaway from Renata's experience at a start-up Venture firm

[00:07:51] - The inspiration for Renegade

[00:11:48] - The most common mistakes made in the early stages of a company

[00:15:14] - Key items to look into first when evaluating companies 

[00:18:04] - Internal superpowers: helping a founder use their strengths

[00:23:46] - Superforecasting: The Art and Science of Prediction

[00:24:04] - What makes a good customer call

[00:25:44] - How more than one Operating Partner changes the conversation and reveals more

[00:27:59] - How businesses have changed in the past few years

[00:30:31] - What companies that have good talent pipelines do to set themselves apart

[00:35:36] - Lessons learned from working with Coda and its CEO, Shishir Mehrotra 

[00:38:12] - Lessons learned from working with MasterClass

[00:41:21] - Differentiating between high and low-quality revenue when evaluating a company

[00:47:39] - What scares them about investing in outliers

[00:51:07] - Improvements made as investors and catalysts for those changes

[00:53:48] - Building an organization that will disrupt itself

[00:56:43] - The kindest thing anyone has ever done for them

 

Aug 24, 2021
Max Simkoff - Redesigning the Home Buying Experience - [Founder’s Field Guide, EP. 47]
01:09:25

My guest today is Max Simkoff, Founder and CEO of Doma. Max founded Doma in 2016 after experiencing the pain and manual process associated with title insurance and real estate transactions. With a background in predictive analytics, Max built Doma to bring a digital-first approach to a historically manual and labor-intensive process. 

 

In our conversation, we cover the history behind mortgage closings, where title companies fall into that process, and how Doma is using technology to improve the client experience. We also discuss Max’s formative experiences at his previous venture, Evolv, and the lessons he’s learned from taking Doma from an idea to a public company. There are many great lessons in this episode, and Max’s entrepreneurial energy shines throughout. Please enjoy this great conversation with Max Simkoff.



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

-----

 

This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

 

-----

 

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

 

-----

 

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

[00:03:17] - [First question] - What Doma does and what they do for customers

[00:04:38] - What Title is and why it sits at the center of such a large transaction

[00:08:41] - Overview of the business economics of this space 

[00:13:55] - How the ecosystem works writ large

[00:18:05] - The formative business experiences he had that led him to today

[00:23:03] - What it means to be great at this whole process

[00:26:53] - The thing Doma tries to predict and the inputs that allow them to do so

[00:32:50] - Defining his biggest roadblocks and how they’ve changed over time

[00:36:02] - Managing stakeholder expectations and perception

[00:40:22] - Learning to walk to the line of having a large vision and communicating it

[00:42:51] - What his loose screw is as a founder

[00:45:06] - The square-peg-round-hole they encountered during the pandemic

[00:51:20] - What the counterproductive byproduct of his genius is

[00:53:35] - Figuring out where to take the company next 

[00:56:52] - The big lessons learned from interacting with capital markets

[00:59:30] - Other entrepreneurs he feels are maniacs that he respects

[01:00:55] - What will be the biggest contributing factors to their success over the next decade

[01:02:44] - The key ingredients for building a winning team

[01:04:34] - The kindest thing anyone has ever done for him




Aug 19, 2021
Suzanne Ciani - Exploring the Creative Process - [Invest Like the Best, EP. 239]
56:34

The intro music you just heard is from my guest today, Suzanne Ciani, an early pioneer of electronic music dating back to the 1970s. As a 5-time Grammy-nominated composer, Suzanne’s music can be heard on her solo albums as well as films, games, and countless commercials. Many have argued her Coca-Cola “pop and pour” changed the sound of advertising forever. 

 

During our conversation, we discuss what it means to be an artist, how to evolve away from the need for approval and validation, and the importance of mentors during the creative process. While many of our guests strive to be lifelong learners - Suzanne seems to take this a step further as a lifelong learner and a lifelong creator. I hope you enjoy my conversation with Suzanne Ciani.

 

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 20,000 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 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

[00:03:53] - [First question] - One of her proudest moments early in her life

[00:05:18] - What she’s learned about originality and its role in the creative process

[00:07:24] - Advice for breaking out of a derivative impulse and finding your character

[00:09:27] - Going from a classically trained pianist to exploring modular synthesis

[00:13:47] - Performing on David Letterman

[00:17:55] - What the Buchla is and the sounds it can make

[00:23:03] - How much of playing a modular synth is improvisational versus pre-made

[00:24:36] - Ways she would design a creative system for other creatives

[00:27:38] - What her interface allows her to do and the mechanics of it

[00:29:07] - Describing what the core sound elements are that she manipulates

[00:32:30] - The role of women in music and how it’s evolved over time

[00:35:06] - What stands out from her mentorship with Ilse Bing

[00:38:16] - Later career creative freedom and what it unlocks for artists

[00:39:25] - Her thoughts on the creative process writ large and its components

[00:42:10] - Commercial sound design and working with Coca-Cola and Atari

[00:44:46] - Observations from a creative life that other artists could benefit from

[00:46:11] - Unifying factors across her best performances

[00:47:53] - What the future might hold for technology and music

[00:50:18] - Where to start when exploring her discography

[00:51:17] - The kindest thing that anyone has ever done for her

Aug 17, 2021
Sameer Shariff - Breaking Language Barriers - [Founder’s Field Guide, EP. 46 ]
54:17

My guest today is Sameer Shariff, co-founder and CEO of Cambly. After starting his career at Google, Sameer founded Cambly in 2013 as an on-demand service to learn English. At the touch of a button, Cambly connects its global user base into a 1-on-1 conversation with an English speaker.

 

During our conversation, we cover the origin story of the business, what Sameer views as the core functions of the two-sided marketplace, and how the team approached scaling a product that was international from day one. Once you hear Sameer talk, you quickly realize the size of Cambly’s market opportunity and why it may have been easy to overlook this problem. I hope you enjoy this great conversation with Sameer Shariff.

 

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

 

-----

 

This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

 

-----

 

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

 

-----

 

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

[00:03:05] - [First question] - What led him to the original concept of Cambly

[00:05:21] - Beginning to learn the scope of the problem and what solving it unlocked 

[00:07:58] - What Cambly is and how they started tackling the problem 

[00:09:15] - Lessons learned about the challenges of building an alive marketplace 

[00:11:41] - Technical challenges and the enabling technologies that allowed it to happen 

[00:12:59] - Deciding on what to focus on first when it comes to students 

[00:15:24] - Figuring out the formula for unit economics and the pricing structure

[00:17:02] - Learning what doesn’t work in their business model

[00:18:07] - Setting up quality control measures and moderation

[00:21:01] - Tools and services that will improve their experience in the future

[00:23:18] - What the 11-star version of Cambly would look like in a decade

[00:26:56] - Ways in which their software and concept could be applied elsewhere

[00:28:30] - Setting themselves up for success and fine-tuning the matchmaking component

[00:30:37] - Driving users to the platform and audience building strategies

[00:33:46] - Making the platform feel native to each country it serves

[00:35:59] - Surprising lessons learned around distribution and market penetration

[00:37:13] - The biggest boss battles faced as a business

[00:40:17] - Advice he would give to founders in a similar situation 

[00:41:32] - How he’s personally changed the most across this journey

[00:43:32] - Ways he’s shifted to a state of letting go and trusting his team more

[00:45:14] - Lessons learned from studying Airbnb

[00:47:22] - The kindest thing anyone has ever done for him 



Aug 12, 2021
Sridhar Ramaswamy - The Past, Present, and Future of Search - [Invest Like the Best, EP. 238]
01:17:00

My guest today is Sridhar Ramaswamy, co-founder and CEO of Neeva and Venture Partner at Greylock. After a 15-year career building Google’s ad business, Sridhar launched Neeva as an ad-free search engine with a focus on personalization and privacy. During our conversation, we dive into the early days of search and what led to Google’s dominance. Sridhar shares his view on the potential end state for ad-based search engines, and how all of his experiences led him to found Neeva. Beyond a great deep dive into the origins of search, this discussion is filled with great lessons about data-driven decisions, the value of partnerships, and balancing revenue opportunities against user experience. I hope you enjoy my conversation with Sridhar Ramaswamy.

 

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 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

[00:03:39] - [First question] - Major chapters of the history of search engine technology 

[00:09:21] - The early days of the page rank revenue model prior to ads 

[00:16:27] - Reputation and quality and how they were applied in Google’s early days

[00:21:10] - Driving variables of Google’s ad model that will drive their business going forward

[00:26:48] - Lessons learned about the importance of partnerships while at Google

[00:33:26] - What is Neeva and what motivated him to start it in the first place

[00:39:11] - Variables in building an ad-free search engine that can compete with Google

[00:44:57] - Thoughts on tracking and privacy in the tech world today writ large

[00:50:09] - Lessons he’s learned about pricing when it comes to software

[00:52:58] - Figuring out finding customers when your addressable market is everyone 

[00:56:20] - What he’s learned about leadership over the course of his career writ large

[00:58:05] - What he’s learned about identifying candidates and winning them over when it comes to recruiting new talent

[01:00:27] - His philosophy on product development in general

[01:02:19] - Framing problems in a way that allows you to reach milestones as you build 

[01:04:43] - His biggest professional mistake and what he learned from it

[01:06:08] - The kindest thing that anyone has ever done for him

[01:07:49] - What Bill Campbell brings to mind when he thinks about him

Aug 10, 2021
Ernie Garcia - Disrupting the Auto Buying Experience - [Founder’s Field Guide, EP. 45]
01:13:52

My guest today is Ernie Garcia, co-founder and CEO of online used car platform, Carvana. Ernie launched Carvana in 2012, and less than a decade later, the business commands a $60 billion valuation while selling a used car every other minute.

 

Our conversation covered a lot of ground. We discussed effective decision-making, what it means to be a long-term thinker, and what Ernie sees as the defining features of attractive markets. We then went deep on Carvana itself, covering the original insight, logistics operations, and counter-intuitive decisions Carvana took as they set about building the brand. I think you’ll find Ernie’s insights and energy infectious. I hope you enjoy this great conversation with Carvana CEO, Ernie Garcia.

 

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

-----

 

This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

 

-----

 

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

 

-----

 

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

[00:03:10] - [First question] - Defining average decision quality and he weaves it into his business

[00:05:40] - How he would assess average decision quality in another company

[00:07:04] - What company culture means to him and building it at Carvana

[00:08:45] - Key features of a market that is desirable to step into as an entrepreneur

[00:10:06] - Various levels of complexity faced in automotive retail

[00:13:51] - Reality Has A Surprising Amount Of Detail; The genesis idea that led to Carvana

[00:17:52] - Critically new things delivered to customers when buying a used car

[00:20:43] - Dealership unit economics vs logistics platform economics and what drives gross profit per unit

[00:24:47] - What is an IRC center, the hub and spoke model, and the skeleton of Carvana

[00:28:44] - The size and scope of one of their fulfillment centers and cost savings involved

[00:30:29] - How the spoke component works and ways it will be improved over time

[00:32:39] - Defining what being a long term thinker means to him

[00:35:50] - The story behind the Carvana car vending machine

[00:39:49] - His thinking on the dual-layer nature of customer experience and communication

[00:41:59] - Mistakes and failures made while learning to become good communicators

[00:44:21] - Great companies get a lot done very fast

[00:48:56] - Infrastructure set in place to maintain their pace as they scale 

[00:51:50] - The embedded formula used for teams to communicate what they want to do

[00:52:50] - What it felt like as a leader going through the pandemic

[00:58:24] - Whether or not COVID-19 has permanently impacted the consumer landscape

[01:00:03] - Businesses, leaders, and things he’s studied that others could learn from

[01:01:55] - Surprising new things arising in the automotive and transport industries

[01:05:23] - The kindest thing anyone has ever done for him



Aug 05, 2021
Karen Karniol-Tambour - All Things Macro - [Invest Like the Best, EP. 237]
01:19:02

My guest today is Karen Karniol-Tambour, Partner and Co-CIO for Sustainability at Bridgewater Associates. You will quickly understand why Ray Dalio described Karen as a “vacuum cleaner of learning” - our conversation covered a variety of market themes, and Karen goes deep on each of them. We touch on inflation, monetary policy, currencies, retail investors, ESG, and how each of these levers has become more important for investors to understand. Karen has a rare skill for making complex ideas seem simple, and I love the frameworks she uses to deconstruct big, important issues. She does such a good job of explaining what’s changed, why it matters, and what to do about it. I hope you enjoy my great conversation with Karen Karniol-Tambour.

 

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 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

[00:03:39] - [First question] - How Bridgewater invests and the experiences that led her there

[00:06:47] - What working with Daniel Kahneman felt like and learning his perspective

[00:08:09] - An example of holding herself to accumulating and stress testing data

[00:10:17] - Important variables to consider when seeking returns in large-scale bets

[00:14:18] - What we should be thinking about in terms of inflation as we look to the future

[00:20:07] - How she thinks about inflation and how she defines it

[00:22:57] - Relevant asset classes that can protect or help diversify against inflation

[00:26:14] - What still largely confuses her about inflation and its many facets

[00:28:05] - Her philosophy and model for understanding the system of currency

[00:33:21] - How investors should think about the US dollar 

[00:35:50] - Whether or not owning an unhedged global equity index gives you currency exposure

[00:37:07] - The fundamental nature of equity markets and household balance sheets

[00:41:37] - Ways the growing wave of retail investors will impact prices and returns 

[00:43:53] - How she’s evolved her valuation approach given our new investor landscape

[00:45:43] - The good and bad roles ESG might play for investors going forward

[00:50:36] - Potential concerns around the growing trend of ESG writ large

[00:53:51] - Thoughts on the 60/40 portfolio and whether or not it’s still worth using

[00:55:32] - Designing a default diversified portfolio in light of markets today

[00:57:45] - Aspects of the global market economy today people should be talking about more

[01:01:15] - Ways she investigates a new topic and how it has evolved over time

[01:04:14] - Variables that matter in investment teams and company cultures

[01:06:53] - How she would approach cryptocurrency and what’s interesting about them

[01:09:08] - A rosey and gloomy take of what the world could look like in a decade

[01:12:37] - The kindest thing that anyone has ever done for her

 

Aug 03, 2021
Sebastian Mejia - Mastering On-Demand Convenience - [Founder’s Field Guide, EP. 44]
56:13

My guest today is Sebastian Mejia, co-founder and president of Rappi. Founded in Bogota, Colombia in 2015, Rappi set out to create an on-demand convenience store and has expanded into nine countries and over 200 cities. In our conversation, Sebastian and I discuss what differentiates Rappi from US-based delivery apps, how the company evolved early by understanding their customers’ behavior, and how the business balances growth vs. unit economics. I loved hearing Sebastian’s views of the value of brands in an increasingly app-based world, the importance of being hyper-local for any delivery-based business, and how fungibility is a key characteristic of any rewards program. I hope you enjoy this great conversation with Sebastian Mejia.

 

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. 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 mentioned content, check out the episode page here.

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This episode is brought to you by Dell Technologies. When you call a Dell Technologies Advisor, they’re focused on you - ready to give advice on everything from laptops to the cloud to keep your small business ready for what’s next. Call an advisor today at 877 ASK DELL, and do more with modern devices and Windows 10 Pro.

 

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This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambiguous problem, then Versett is the firm to call. To check them out, visit versett.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

[00:02:54] - [First question] - What the Rappi is their current scale and user base 

[00:05:30] - The early-stage problems they encountered when building their platform 

[00:08:43] - Building the initial network dynamics and unit economics of couriers  

[00:12:35] - Solving the data collection and integration needed to power Rappi 

[00:15:22] - Defining what local means  and the difference between units and zones

[00:17:33] - Other active companies that offer a similar service  

[00:18:27] - Thoughts on making money in such a diversified supply chain

[00:22:57] - The moment they realized they were starting to feel scale effects for the first time

[00:25:11] - Questions they’re asking themselves as they continue to grow

[00:28:20] - Streaming consumer goods and how they’ll change consumer behavior

[00:31:45] - Impacts on brands Rappi might have with larger user adoption

[00:34:34] - Unique attributes and opportunities in Latin American markets today

[00:38:45] - Observations of early investors and questions investors as him often

[00:40:17] - The value unlock of having a subscription model akin to Amazon prime

[00:44:47] - How crypto and blockchain technology might benefit Rappi users

[00:47:16] - His perspective on crypto in Latin America today compared to the US 

[00:48:09] - Their work in financial services

[00:47:30] - Possible reasons why Rappi might not succeed in the future

[00:50:30] - The kindest thing anyone has ever done for him

 

Jul 29, 2021
Carl Kawaja - Wisdom from Decades of Investing - [Invest Like the Best, EP. 236]
01:28:11

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

Jul 27, 2021
Stewart Butterfield - We Don’t Sell Saddles Here - [Founder’s Field Guide, EP. 43]
01:06:48

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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This episode is brought to you by Dell Technologies. When you call a Dell Technologies Advisor, they’re focused on you - ready to give advice on everything from laptops to the cloud to keep your small business ready for what’s next. Call an advisor today at 877 ASK DELL, and do more with modern devices and Windows 10 Pro.

 

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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.

 

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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

Jul 22, 2021
Steve Mandel - Investing Behind Change - [Invest Like the Best, EP. 235]
01:10:23

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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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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com.

 

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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

Jul 20, 2021
Spenser Skates - Challenging Big Ideas - [Founder’s Field Guide, EP. 42]
58:16

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

Jul 15, 2021
David Sacks - How to Operate a SaaS Startup - [Invest Like the Best, EP. 234]
01:01:33

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.

 

------

 

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

Jul 13, 2021
David Vélez - Building the Branchless Bank - [Founder’s Field Guide, EP. 41]
56:44

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

Jul 08, 2021
Balaji Srinivasan - Optimizing Your Inputs - [Invest Like the Best, EP. 233]
01:45:32

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.

 

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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] - 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

Jul 06, 2021
Michael Mayer - Business Boss Battles - [Founder’s Field Guide, EP. 40]
01:01:49

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

 

-----

 

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

 

Jul 01, 2021
Marc Andreessen - Making the Future - [Invest Like the Best, EP. 232]
01:19:42

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.

------

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.

 

------

 

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

Jun 29, 2021
Will Ahmed - Optimizing Human Performance – [Founder’s Field Guide, EP. 39]
01:11:26

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.

-----

 

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

Jun 24, 2021
Howard Marks - Embracing the Psychology of Investing - [Invest Like the Best, EP. 231]
58:10

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.

------

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

Jun 22, 2021
Christina Cacioppo - Building the New Standard in Security – [Founder’s Field Guide, EP. 38]
01:03:46

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.

-----

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] - 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

 

Jun 17, 2021
John Harris - Resilience and Imagination - [Invest Like the Best, EP. 230]
59:40

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

Jun 15, 2021
Florian Hagenbuch and Mate Pencz - Everything Will Be Bought Online – [Founder’s Field Guide, EP. 37]
57:02

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

Jun 10, 2021
Gabriel Leydon - Designing Digital Economies - [Invest Like the Best, EP. 229]
01:17:46

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.

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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

[00:03:59] - [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

Jun 08, 2021
Assaf Wand - Innovation in Static Industries – [Founder’s Field Guide, EP. 36]
57:46

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.

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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

[00:02:44] - [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

Jun 03, 2021
Dennis Lynch - Delivering Alpha in Adapting Markets - [Invest Like the Best, EP. 228]
01:10:59

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.

 

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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

[00:03:47] - [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

Jun 01, 2021
Henrique Dubugras - Building the Financial Center of Gravity – [Founder’s Field Guide, EP. 35]
01:00:25

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.

-----

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

[00:02:53] - [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

May 27, 2021
Justin Fishner-Wolfson - Secondary Investing in Private Markets - [Invest Like the Best, EP. 227]
01:07:07

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.

------

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.

 

------

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

[00:03:47] - [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

 

May 25, 2021
Peter Reinhardt - Learning How to Sell – [Founder’s Field Guide, EP. 34]
01:02:27

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.

-----

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] - 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

 

May 20, 2021
Brent Beshore - Learnings from a Year of Unexpected Events - [Invest Like the Best, EP. 226]
01:08:36

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.

------

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.

------

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

[00:03:52] - [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

May 18, 2021
Jeremy Cai - Manufacturer to Customer – [Founder’s Field Guide, EP. 33]
50:50

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.

-----

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

May 13, 2021
Eli Dourado - Frontiers for Productivity - [Invest Like the Best, EP. 225]
56:11

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.

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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 – 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

[00:03:28] - [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




May 11, 2021
James Reinhart – Lessons in Process Power – [Founder’s Field Guide, EP. 32]
52:43

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.

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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] - 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

May 06, 2021
Andrew Sugrue - Investing in Paradigm Shifts - [Invest Like the Best, EP. 224]
01:02:18

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.

------

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

[00:03:31] - [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

May 04, 2021
Alyssa Ravasio - Supply, Demand, and the Outdoors - [Founder’s Field Guide, EP. 31]
01:02:50