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.   ------   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 [00:13:35] - 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.   ------   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 [00:13:11] - 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  [00:49:26] - 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. ------   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.   -----   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. ------   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.   ------   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.   ------   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 [00:15:11] - 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  [00:43:24] - 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 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  [00:20:57] - Overview of building an AI learning model and applying it to loans [00:25:16] - Machine learning algorithms and interwoven programmer bias [00:28:34] - Revenue model and transactions that fund Upstart  [00:31:43] - Who the typical customer is and their user experience [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 [00:49:43] - 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.   ------   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 $1m 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 $1.5b 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.   -----   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 [00:29:02] - 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. ------   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. -----   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