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

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.  ---- 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

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

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.   ------   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 [00:02:53] - [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

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.   ------   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 

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.   -----   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.   -----   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.   -----   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

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.   ------   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 [email protected].    ------   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 

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.   ------   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 [email protected].  ------   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

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.   ------   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  

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.   -----   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

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.   ------   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.    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

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. -----   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 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.    -----   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

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. ------   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 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 [email protected].    ------   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

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.   -----   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 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.    -----   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 

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.   ------   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, 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

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.   -----   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 [00:02:47] - [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 

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.   ------   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

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.   -----   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

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 [email protected].    ------   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  

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  

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 [email protected].    ------   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  

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

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

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 

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

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

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. ------   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] - 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  

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. -----   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.   -----   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 [00:02:54] - [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  

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. ------   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 [00:03:38] - [First question] - The two companies he has owned the longest and what they’ve taught him as an investor  [00:16:37] - Discussing his investment style through the lens of simplicity   [00:24:35] - A time where he worked to try and create a simplified equation but couldn’t  [00:30:59] - Discussing his investment style through the lens of echolocation and ambiguity  [00:36:03] - Thoughts on whether buying well or holding well is more difficult [00:40:40] - Capital Group’s history and his river-rafting analogy in regards to the company [00:47:48] - What he means by “The Empire Strikes Back” and relevant market themes [00:54:50] - A brief summary of “The Empire Strikes Back” [00:58:42] - Common reasons that he may have gotten something really wrong  [01:03:34] - Impressions made on him by the poet Rilke [01:09:00] - The work of Brunello Cucinelli and the nature of quality  [01:13:08] - Advice for new investors who want to step into the field and set themselves up for success [01:13:54] - The Visual Display of Quantitative Information  [01:17:39] - What he’s learned about kindness [01:19:54] - The kindest thing that anyone has ever done for him

My guest today is Stewart Butterfield, founder and CEO of Slack. Stewart’s 2014 essay “Why We Don’t Sell Saddles Here” had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models and behavior when introducing innovative products. I hope you enjoy my conversation with Stewart.   Before we transition to the episode, I also wanted to highlight our newest series Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. For more information go to joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. -----   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.   -----   This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device.   When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply.   -----   Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:51] - [First question] - Discussing his essay We Don’t Sell Saddles Here   [00:06:19] - Important contrast between innovation and the product [00:06:46] - Who Do You Want Your Customers to Become?  [00:08:07] - His thoughts on marketing from both ends and how he’s gotten better at it [00:10:45] - What across Slack’s history has been the most successful market messaging creation strategy [00:13:43] - The 5K contest and how it taught him about the design unlock of limitations [00:17:44] - How limitations and constraints can power and incentivize innovation  [00:21:21] - Why both of his attempts to build videogames ended up as consumer software [00:27:55] - Whether or not there is still white space in digital communication software [00:30:15] - The dynamic between effective communication and building communication tools [00:34:02] - A future of digital-first companies and what that might look like [00:40:15] - Leadership and Self-Deception and what self-deception means to him [00:43:39] - Examples of self-deception he underwent that he was able to learn from [00:46:59] - Mastery and its importance in the world of business [00:48:59] - Why hippies and APIs may have a tighter correlation than we think  [00:54:01] - Whether or not technology is fundamentally amoral  [00:56:10] - Interesting and open questions about the future that remain unanswered  [00:58:33] - His current creative outlets that he engages with the most  [00:59:24] - Yahoo Resignation Letter and why he wrote it the way he did [01:00:31] - Lessons for investors and builders that he’s learned from building Slack [01:03:07] - The kindest thing that anyone has ever done for him  [01:04:27] - Why a philosophy primer would be beneficial for virtually everyone

My guest today is Steve Mandel, founder of Lone Pine Capital, one of the most successful hedge fund and investment firms of this generation. In our conversation, we discuss how the investing business has evolved since Steve’s start in the 1980s, why it’s so difficult to drive alpha by shorting stocks today versus 20 years ago, and why Steve still loves to get into the guts of a business. Steve shares his lessons through a variety of great stories, which made this such a fun experience. Please enjoy my conversation with Steve Mandel.   Before we transition to my interview with Steve, I’d also like to highlight the newest Colossus show, Business Breakdowns. If you like Steve’s idea of getting into the guts of a business, this is the show for you. Please find a list of our episodes at joincolossus.com and subscribe to Business Breakdowns on your preferred podcast player.   I hope you enjoy my conversation with Steve Mandel.    For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------   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 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 [email protected].   ------   Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:36] - [First question] - His first encounter with Walmart [00:05:51] - What about Sam Walton made him worth idolizing  [00:08:14] - The juxtaposition of business to management quality [00:10:57] - Why a career in retail influenced the lens he sees the investing world through [00:11:23] - What bad company culture in retail looks like [00:12:33] - Aspects of Walmart’s culture that could be applied to other companies [00:13:54] - Defining the core essence of retail company culture [00:15:02] - How long it used to take for a stock to properly reflect new information [00:16:40] - The nature of edge and what it looked like back then [00:21:09] - Investing behind change and assessing trends [00:23:06] - Scars and stories from just how vicious short markets can be [00:26:32] - Thoughts on building an enduring firm and how it’s evolved over time  [00:32:14] - The process and decision to remove himself from the day-to-day operations [00:33:55] - Lessons learned over time about what separates good from bad analysts [00:34:42] - Where to start looking when getting into the guts of a business [00:36:31] - What is most exciting when you’re inside the guts   [00:39:19] - Interesting aspects about payments today writ large [00:42:15] - Broad trends around change in consumer trends  [00:43:02] - How he views software businesses looking forward as an investor [00:45:14] - Great managers and their emphasis on analyzing their competitive advantage [00:48:02] - Ways that pace as a variable has changed in importance [00:49:27] - What he thinks we’ll look back on as silly in how markets currently operate [00:50:33] - Whether or not all markets becoming 24/7 will be a good thing [00:51:59] - Big iconic business stories that newcomers should study [00:56:06] - Whether or not business building is an art form [00:57:38] - Key levers that typically always matter for a business [00:59:53] - Other major aspects of the world that are important to consider [01:01:13] - How his personal motivations morphed over the years and what has changed [01:02:55] - Valuable lessons learned about the inputs and outputs of education [01:04:15] - Advice for would-be future investment analysts [01:05:46] - The kindest thing anyone has ever done for him

My guest today is Spenser Skates, CEO and co-founder of Amplitude Analytics. Spenser founded Amplitude in 2012 with a thesis that building the best product requires, deep cross-functional understanding of customer behavior. During our conversation, we discuss Spenser’s long history in programming and how his early experiences tie into his work today. We also explore the nuances of equity compensation, how different VCs can play a role in the success of a startup, and Spenser’s desire to see more direct listings vs. IPOs. While many founders follow the path of others, it is clear Spenser takes time to challenge the status quo.   Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. In this episode, you will hear how Spenser’s team worked with the meditation app, Calm, to optimize for customer growth. It was particularly interesting to hear this story after listening to the Calm breakdown. Find episodes of Business Breakdowns on your preferred podcast provider or on joincolossus.com   I hope you enjoy my conversation with Spenser Skates.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. -----   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.   -----   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 [00:03:15] - [First question] - How he won the Battlecode tournament at MIT twice [00:06:43] - A few key insights that helped him win the tournaments [00:08:34] - Lessons learned at MIT and the road to starting Amplitude [00:13:57] - A typical customer experience when using Amplitude  [00:17:17] - How their platform extrapolates key data points in user data that others don’t [00:19:03] - His most productive mistakes made while building the company  [00:21:10] - The strange history of equity and his thoughts on how it should be used  [00:28:08] - The recent changes in the vesting schedule for newly issued equity  [00:29:59] - Lessons learned from working with some of the best investors out there [00:36:20] - His thoughts on the IPO process and going public writ large [00:41:04] - The role the SEC plays and his perspective on SPACs  [00:44:01] - Differences in direct listings compared to traditional IPOs  [00:48:36] - His thoughts on dual-class structures and corporate governance  [00:50:11] - Hopes for Amplitude as he looks five years into the future [00:52:03] - The potential value unlock of smart software for end-users   [00:55:08] - The kindest thing that anyone has ever done for him

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

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. ----- 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   -----   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 [00:02:55] - [First question] - Why Berkshire Hathaway took such an interest in Nubank [00:04:46] - Key differentiators between Nubank and other incumbent banks [00:07:11] - Onboarding user experience and overview of customer acquisition [00:10:38] - The original problem Nubank wanted to solve and how they approached it [00:15:32] - Lessons from working at Sequoia about great FinTech businesses [00:19:18] - What parts of his personality and life experience worked its way into NuBank [00:23:18] - Obstacles that needed to be overcome in order to serve the Brazilian public [00:27:52] - Transparency and patience needed to overcome a complicated problem [00:31:11] - Nubank’s business economics compared to other banks [00:34:46] - Overview of rewards programs and why customers like them so much [00:37:27] - Best questions asked that explained Nubank’s market opportunity [00:42:02] - Second layer unit economics of the company and where to look for them [00:45:51] - How far we are into the Latin American technological ecosystem’s development [00:47:24] - Lessons learned from some of the worst decisions he’s made as a founder [00:51:30] - What he’s most excited about for the future [00:54:19] - The kindest thing anyone has ever done for him

My guest today is Balaji Srinivasan, a serial entrepreneur and angel investor. Balaji is known to challenge conventional wisdom, and he lives up to his reputation in this conversation. We discuss a wide variety of topics, including advancements in health tracking, ways to evaluate your own information diet, and how technology is driving decentralization and what that could mean for countries, corporations, and individuals.   Before we transition to the episode, if you enjoy this conversation with Balaji, I’d recommend the Ethereum episode on our newest show, Business Breakdowns. You can find that episode and more on your favorite podcast player or at joincolossus.com. Please enjoy my conversation with Balaji Srinivasan.   For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------   This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Marqeta, Oatly, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.   ------   This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick".   ------   Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:30] - [First question] - Thoughts on information diets and how they influence individuals [00:21:37] - Ways to optimize your diet by reading the source material and consuming less news [00:26:40] - Understanding the informational supply chain and tracing data back to the origin [00:41:07] - Modern cities, the nature of a group of individuals, and what sovereignty may mean in the coming years [00:53:52] - Key ingredients and main components needed for a successful startup city [01:11:35] - Social impacts from everyone becoming an investor and how it ties into everything [01:25:49] - Recommendations and a personal prescription for longevity, health, and wealth [01:37:32] - The kindest thing anyone has ever done for him

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

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.   ------   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

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

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

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  

My guest today is John Harris, Managing Partner of Ruane, Cunniff & Goldfarb, where the flagship Sequoia Fund has an incredible 50-year track record running a highly concentrated portfolio of equities. In our conversation, we cover John’s approach to finding businesses that can be owned for the long-term, what goes into their diligence process, and the importance of resilience for investors. I think many of the stock pickers will enjoy many of the points on good management, good businesses, and using imagination. I hope you enjoy my conversation with John.   For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.   With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.   ------ This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.   ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:48] - [First question] - How markets undervalue long-duration growth of companies [00:07:21] - Why should one even do DCFs at all [00:10:01] - Defining homework when studying a business and what getting better as you do your homework tends to look like [00:12:24] - How the market still underestimates how the quality of a company reduces risk [00:15:09] - Reinvestment opportunity and risk and why they’re important for long term returns [00:17:14] - Lessons learned owning Google stock options for over a decade [00:22:02] - Skill versus luck when it comes to investing psychology [00:24:32] - Perspectives on big market cap companies in a portfolio when success often comes from smaller-cap non-linear growth  [00:26:47] - Features of the current market landscape that he finds interesting [00:31:24] - What buying behavior looks like in the demand side of the business equation [00:34:10] - Discovering a company that served the customer and was a delight to discover [00:37:58] - Analysing getting one's hands dirty to get a competitive advantage in serving the customer [00:39:24] - The hardest episode of his investing career and what he learned from it [00:43:03] - Reasons why a company succeeded after doing a deep dive but not buying in [00:43:54] - One of the CEOs he finds most remarkable [00:47:20] - Examples of businesses where scale isn’t the driver of competitive advantage [00:49:50] - A company they owned that did well but didn’t have the strongest company culture [00:50:56] - His view on the investment industry today writ large [00:52:16] - Ways investors could expand their imagination when analyzing businesses [00:53:07] - The kindest thing anyone has ever done for him

My guests today are Florian Hagenbuch and Mate Pencz, co-founders of Loft. Based in Sao Paulo, Brazil, Loft is a digital platform designed to bring Latin American real estate into the e-commerce age. The 3-year-old startup scaled to over $150mm in annualized revenue in 2020 and is on track for multiples higher this year. We dive into the market opportunity in Brazilian real estate and how that differs from the US market, the value proposition for iBuying across the US and Latin America ecosystems, and touch on the potential for Loft to expand from real estate into adjacent services such as mortgages. Florian and Mate are second-time founders and have some great lessons shared throughout the episode. Please enjoy my conversation with Florian and Mate.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.   See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." -----   Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:52] - [First question] - Why Latin America currently presents such a unique opportunity for modern technology companies [00:04:38] - What the market looked like when they started Loft [00:07:20] - How they approached gathering data that wasn’t available or accessible in order to develop the company infrastructure [00:09:39] - How the process of buying a home used to be in São Paulo versus today [00:12:19] - What Loft’s hard work unlocks for consumers and home buyers [00:14:06] - What iBuying feels like writ large and more specifically in real estate [00:18:07] - Analysis of an iBuying real estate transaction from start to finish [00:20:09] - The role machine learning plays in property valuation and building that feature   [00:22:50] - Defining their business model and being a fulfillment center aggregator  [00:24:47] - Notable characteristics of the iBuying market in the United States  [00:27:00] - How they think about the competitive advantage extensions of Loft  [00:29:53] - Exciting opportunities for the FinTech broadly in Latin America  [00:32:47] - Deciding on what it is they want to tackle next as they grow the company  [00:34:13] - Thinking about the value proposition to customers and how they market it  [00:35:50] - Lessons learned about building businesses early on that were applied to Loft [00:40:12] - What led them to finding their early product-market fit  [00:42:48] - Calibrating and defining their ambitions for Loft out of the gate  [00:45:05] - Important and interesting trends in the business world today writ large  [00:48:43] - Further lessons and key challenges around building and scaling Loft  [00:52:24] - The kindest things that anyone has ever done for them

My guest is Gabe Leydon, who is the co-founder and former CEO of MZ, also known as Machine Zone, the company behind huge games such as Mobile Strike and Game of War. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I have talked to in a long time. In our conversation, we cover why great design can be a bad sign that we’d run out of ways to innovate, the most important lessons from human psychology for building games and products, and why products which are busted or breaking but still booming can be great investment opportunities. This conversation rewired my brain on many levels, so I’m excited for you to listen. Take the red pill with us, and please enjoy my conversation with Gabe Leydon.   For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.   With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:59] - [First question] - Thoughts on the importance of design and the role it plays in capitalism writ large [00:07:26] - Huxley’s vision of the future versus Orwell’s - Amusing Ourselves to Death [00:10:49] - A question about game design in interviews that no one can answer well [00:18:27] - What about his early experiences that allowed him to be good at answering that question when others could not [00:26:35] - Another example to further explain the nature of meta software design mechanics [00:29:44] - Characteristics of what drives players to spend money in games [00:34:46] - Defining heroic spending and the group dynamics of spending gamification [00:38:18] - Skill set required to design an economy and what makes it so difficult [00:41:27] - Cosmetic purchases as a revenue stream in North American video games [00:43:56] - What he’s learned about human psychology through his design work [00:45:48] - How the technological infrastructure developed in building video games overlap in performance marketing [00:48:44] - His experience with the RT platform and some of the technologies he’s built [00:55:49] - Celebrity NFTs and a shift to becoming virtual manufacturers in the future [00:59:58] - What businesses can do now to prepare for and adapt to NFTs [01:01:03] - Why we need AI more than think we might [01:04:32] - What he plans to do with his skillset if the world becomes increasingly gamified [01:05:40] - Companies with poor design may be indicative of an attractive acquisition [01:08:11] - How differing cultural perspectives on video game design permeate into NFTs [01:08:46] - Defining the Chinese item box approach to in-game player rewards [01:11:24] - The kindest thing that anyone has ever done for him

My guest today is Assaf Wand, CEO, and co-founder of Hippo, a homeowner insurance startup founded in 2015. In March 2021, Hippo announced a SPAC merger, valuing the business at over $5bn. In our discussion, we cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners has opened up Hippo's business model to a wide range of opportunities. I was excited to speak with Assaf, given his experience as a serial entrepreneur, and he did not disappoint. Please enjoy my conversation with Assaf Wand.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.   See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:44] - [First question] - His philosophy on business [00:04:04] - His first experience in entrepreneurship [00:05:03] - Lawyers vs entrepreneurs [00:07:03] - Major lessons taking risk in entrepreneurship [00:11:14] - Importance of speed in business [00:15:02] - Increasing urgency into the business as a leader [00:18:59] - What the insurance sector was like at the start of Hippo [00:24:49] - Steps he took to bootstrap trust [00:27:03] - Convincing partners [00:29:04] - Building the products and distribution [00:32:49] - Thoughts on innovators dilemma [00:35:00] - Flaws within the insurance industry [00:34:57] - Vision for the firm  [00:37:44] - Importance of culture in company building [00:41:19] - Storytelling as an essential piece of company building [00:41:50] - Building and managing a roadmap [00:43:19] - What does it mean to respect the customer [00:46:11] - Defensibility of the insurance industry [00:49:34] - Rewards of the trench warfare of entrepreneurship [00:53:33] - The feeling of getting wealthy  [00:55:29] - Kindest thing anyone has done for him

My guest today is Dennis Lynch, Head of Counterpoint Global, where he oversees over $100bn in AUM and boasts one of the strongest track records of any public investor. In our conversation, we cover Dennis's unique approach to building a research team, how misclassification of companies often creates the highest upside opportunities, and how Dennis has adapted his investment process over the past 20 years. I think Dennis defines what it means to be intellectually honest, and you will hear that in his answers throughout our discussion. I hope you enjoy my conversation with Dennis Lynch.   For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.   (for me-  )   ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.   With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.   ------ This episode is brought to you by MIT Investment Management Company (MITIMCo), the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term.   MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:47] - [First question] - How he would teach potential students to be investors [00:04:26] - The Money Game [00:04:40] - Moneyball [00:05:59] - Pros and cons of volatility when investing [00:08:55] - Emotional response to volatility [00:12:44] - Training to have a better temperament [00:14:20] - What is his investing game [00:15:17] - The Ethical Algorithm [00:16:44] - How time horizon impacts their investment strategy [00:20:53] - Assessing a company’s earnings power [00:26:12] - Shifting business models vs. evolving within a business model [00:32:32] - Understanding how to invest in disruptive businesses [00:35:26] - Why he’s skeptical on Growth and Value investing strategies [00:38:42] - Expectations Investing [00:38:55] - How his view of assessing businesses has changed [00:43:56] - Defining unit economics [00:45:41] - Taking on uncertainty risk in the portfolio  [00:50:38] - The business that taught him the most; Amazon [00:53:32] - Dealing with massive amounts of change [00:56:01] - The Big Short [00:59:46] - Interest in psychedelic research [01:01:02] - What has changed the most in investing from when he started [01:04:19] - Kindest thing anyone has done for him

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

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  

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  

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

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