Invest Like the Best with Patrick O'Shaughnessy

Almost exactly a year ago, Colossus entered into a partnership with David Senra and the Founders podcast to join the Colossus network. The show has since exploded with more devoted fans than any podcast that I've encountered. With that in mind, we are excited to share an example episode from his show here today on the director, James Cameron. It's my favorite recent episode of David's. Please enjoy this episode, and if you haven't already, subscribe to Founders. This is what he learned from reading The Futurist: The Life and Films of James Cameron by Rebecca Keegan and The Return of James Cameron, Box Office King by Zach Baron. Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you byTegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visitingtegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:04:00) - I watched Titanic at the Titanic. And he actually replied: Yeah, but ImadeTitanic at the Titanic. (00:07:10) - I like difficult. I’m attracted by difficult. Difficult is a fucking magnet for me. I go straight to difficult. And I think it probably goes back to this idea that there are lots of smart, really gifted, really talented filmmakers out there that just can’t do the difficult stuff. So that gives me a tactical edge to do something nobody else has ever seen, because the really gifted people don’t fucking want to do it. (00:07:20) - At 68 years old, Cameron wakes up at 4:45 AM and often kick boxes in the morning. (00:07:45) - Self-doubt is not something Cameron has a lot of experience with. His confidence preceded his achievements. (00:09:00) - I basically gave myself a college education in visual effects and cinematography while I was driving a truck. (00:16:00) - Every idea is a work in progress. (00:17:30) - He's been on a planet of his own making ever since. (00:18:00) -The Return of James Cameron, Box Office Kingby Zach Baron (00:22:00) - His outlook is that we can take fate in our own hands. (00:34:00) - Cameron had only been at Corman's for a matter of days, but he was already taking charge. He seems constitutionally incapable of doing otherwise. (What a line!) (00:35:30) - Your mediocrity is my opportunity. (00:37:40) - Cameron finds writing torture. He does it anyway. (00:43:00) - Cameron is willing to let ideas marinate for decades. (00:55:30) - I'd just made T2 for Carolco and I admired how they rolled, being their own bosses, mavericks, entrepreneurs. (00:57:30) - Mute the world. Build your own world. (01:04:50) - Opportunity is a strange beast. It commonly appears after a loss. Buy a book: All thebooksfeatured on Founders Podcast.

My guest today is Lee Ainslie, the founder of Maverick Capital. Lee started his investing career at Tiger Management where he worked for Julian Robertson. In 1993, he left to start Maverick and has built the firm into one of the top-performing hedge funds of the last 30 years. Lee doesn’t speak in public often so this is a fascinating insight into what it takes to build an enduring investment business - both psychologically and operationally. Throughout the conversation, we flick between his lessons building Maverick, his perspective on the market, and what he’s learned about the craft of investing. I hope you enjoy this great conversation with Lee Ainslie. Listen to Founders Podcast Founders Episode 311: James Cameron Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/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 (00:03:00) - (First question) - Lee tells us about his relationship with Steve Mandel (00:04:29) - Why he thinks Steve gave him a hand into the role he excelled at (00:07:22) - The concept behind investment talent (00:13:08) - Steps he takes to hire the right individuals for his team (00:16:14) - Why he stepped out on his own to start Maverick Capital (00:20:48) - What he thinks makes for a great investment or stock purchase (00:25:16) - How Maverick maintains its edge over other comparable firms (00:28:31) - Features of a business that get his attention in a unique way (00:32:03) - What he learned from Sol Price (00:38:21) - The difficult aspects of portfolio construction (00:42:04) - How zero interest rates affected the long short style of investing (00:47:22) - Positioning his team for success against other competitors (00:50:32) - How private market activity can affect public market activity (00:54:27) - Software companies and their strengths and weaknesses in the investment market (00:59:33) - Things he tells his team to watch for (01:04:10) - What Lee's learned about money (01:07:02) - The most important conversation he’s had in Mavericks history (01:12:38) - Advice for senior executives trying to pass on responsibilities to others (01:17:54) - What the next ten years for Maverick Capital look like (01:20:42) - Things Lee and Warren Buffett disagree on (01:24:11) - The components of a great investment pitch (01:25:08) - The hardest question anyone could ask him (01:28:48) - What he thinks is important having started Maverick Ventures (01:31:32) - The kindest thing anyone has ever done for Lee

Today, we are running a special episode from our show Founder's Field Guide. In this conversation, Nick Kokonas shares his experience of bringing a business mindset to the restaurant industry. It is one of our favorites at Colossus and there is something for everyone in this timeless conversation. Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (3:02) – (First question) – Why he thinks it’s so important to own something (4:35) – Make decisions that have outcomes (7:00) – His interest in the restaurant business (8:54) – Why restaurants are so tough  (12:05) – How their business mindset changed their running of the restaurant (14:35) – Words they would avoid in the restaurant  (16:19) – Asking the right questions in the restaurant business (20:40) – Importance in taking the right risks (22:02) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing (30:08) – Can dynamic pricing be extended to other businesses (31:20) – Origin of Tock (36:17) – Early days of Tock and identifying the right customers/challenges (41:33) – Importance of the first customer  (44:22) – The typical restaurant business model (49:23) – Lessons from Tock and the importance of knowing what your selling (53:47) – Lessons from publishing (55:44) – Other aspects of business that people know but do nothing about  (1:00:19) – Their response to Covid and lessons learned (1:07:43) – The real impact to the food delivery companies (1:09:24) – How businesses communicate their end processes to their customers (1:14:07) – Kindest thing anyone has done for him

My guest today is Des Traynor. Des is the co-founder and Chief Strategy Officer of Intercom - a customer service solution that helps businesses answer product questions, offer instant support, and automate sales. The business was founded in 2011 and its products operate within 25,000 businesses, including the likes of Amazon, Lyft and Atlassian. Our conversation is roughly split in half. First, we talk about AI and how it’s actually changing businesses like Intercom through products such as their OpenAI powered bot called Fin. We then talk about Des’s views as an investor, which includes an answer about software that I’ll remember for a long time. Please enjoy my conversation with Des Traynor. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/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 (00:03:42) - (First question) - Des's high level thoughts on Open AI and new technology (00:07:07) - Advanced AI tech for existing businesses versus start-ups ventures  (00:11:14) - Where Intercom falls on the spectrum of existing and new AI technology  (00:13:16) - Training AI to be tailored to specific fields of work (00:18:25) - The natural end point is for Intercom incorporating AI   (00:22:25) - Des's product philosophy behind this technology (00:24:03) - Choosing an AI provider that best suited his customer service industry needs (00:26:55) - The value comparison between using AI-led customer service versus human (00:29:18) - Why outsourcing automated data is not for everyone (00:31:15) - Des's advice for other companies beginning to integrate AI into their operations   (00:36:33) - What he is excited for as an investor in this area (00:37:50) - The most common discussions he’s having about this technology (00:41:21) - The inherent risks of using AI models that are not 100% accurate  (00:45:10) - Des's evolution as an investor (00:48:25) - How Intercom solved it’s AI execution problems (00:50:46) - Combating other companies that are trying to overtake the field  (00:53:44) - Counter arguments for using AI technology   (00:57:22) - His view on the best software out there (01:03:00) - The kindest thing anyone has ever done for him 

My guest today is Samo Burja. Samo is the founder of consulting firm, Bismark Analysis, and has dedicated his life’s work to understanding why there has never been an immortal society. His research focuses on institutions, the founders behind them, how they rise and why they always fall in the end. As you’ll hear, Samo has an encyclopedic grasp of history and his work has led him to some fascinating theories about human progress, the nature of exceptional founders, and the future of different societies across the world. Please enjoy my conversation with Samo Burja. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/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 (00:02:52) - (First question) - The core thesis behind the Great Founder Theory (00:06:40) - Great ideas inevitably being discovered at some point in history  (00:08:45) - The historic implications of a global adoption of the Great Founder Theory (00:10:51) - The different possible directions of future trends (00:17:08) - Distinctions between great founders versus live players   (00:22:15) - Common misconceptions about what qualifies one as a great founder (00:24:38) - Noteworthy great founders in the United States (00:28:34) - Recurring observable traits and common themes of great founders   (00:31:29) - Using caution when projecting a mythic lens onto great founders  (00:37:53) - Social technology as the upstream effects of prior material technology (00:43:32) - Whether or not institutions play a role in propagating the work of great founders    (00:49:08) - The role of power and differences between owned and borrowed power   (00:56:51) - Additional ideas that play an outsized role in shaping the world  (01:01:09) - A differing worldview to his own that he finds interesting (01:04:53) - Whether or not capital allocators can benefit from the Great Founder Theory  (01:07:37) - The kindest thing anyone has ever done for him

My guest today is Chris Paik, who is a General Partner at early-stage venture firm, Pace Capital. Before Pace, Chris spent eight years building and investing alongside last week’s guest, Josh Kushner, at his firm Thrive Capital. During that time, he sat on the board of Twitch. Our conversation explores Chris’ frameworks for investing, from atomic value swaps to business model product fit and the seven deadly sins. We also discuss different consumer trends like the rise of virtual YouTubers, Apple’s Vision Pro, and why everyone graduates off YouTube. Please enjoy my conversation with Chris Paik. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/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 (00:03:00) - (First question) - The history of humanity as a data storage and transfer problem and how that relates to new kinds of computer interfaces (00:14:47) - Investing strategies; knowing when to invest in new technology (00:16:39) - Assessing the gray areas of a potential investment (00:22:13) - CodeMiko and VTubing (00:32:51) - An explanation of atomic value swap (00:39:55) - The 7 deadly sins and the degrees to which each sin is monetizable  (00:45:05) - Evaluating the people behind new technologies (00:50:03) - The Reddit Revolt - the current changes happening at Reddit   (00:53:09) - Business model alignment; the steps to take when determining a business’ value capture mechanism  (01:03:52) - The investment decision that Chris is most proud of  (01:08:14) - The consumer investing landscape today (01:11:19) - Chris’ methods for finding new content, technology and potential investments on the internet (01:14:06) - The fundamentals of value creation   (01:15:06) - The dark side of tech, how can it be more than just friction reduction (01:17:22) - Chris’ opinion on why so many innovations come from the US (01:20:37) - Defining market places and how to start and grow a successful one (01:23:23) - Chris’ thoughts on opportunities with bad business models (01:26:19) - A breakdown of Chris’ analogy “Sculptors versus painters” (01:29:34) - The kindest thing that anyone has ever done for Chris

My guest today is Josh Kushner, founder and managing partner of venture firm, Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Thrive has gone from strength to strength since then and now manages $15 billion with a small team of 9 investors. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Josh rarely speaks in public about the firm and their philosophy so it was a blast to do this with him. Please enjoy my great conversation with Josh Kushner. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:14) - (First question) - Why do this podcast (00:06:14) - The development of taste and quality  (00:10:20) - CS Lewis tweet; The Inner Ring (00:11:53) - Founders being heroes and motivating quietly from the background (00:16:14) - Overview the founding story of Oscar Health (00:21:30) - Is a big business different from a small one (00:23:18) - Learning to identify good problems and creating a business to solve it  (00:25:43) - The birth story of Thrive Capital  (00:30:14) - Lessons learned from creating the first three Thrive funds (00:33:35) - Industry wide competition today and models for building a firm in general  (00:37:44) - Talent, recruiting and seeing potential in younger generations of people (00:45:40) - Investments he made during the early foundation of Thrive that had significant impact  (00:49:12) - His analogy for investing in early versus late stage (00:54:22) - The current macro environment (00:57:52) - Giving AI companies computing power instead of money (00:58:57) - Why he sold small stakes of Thrive  (01:03:10) - His philosophy on what makes a good product (01:05:20) - What he thinks about the models like Mobile and Cloud  (01:08:10) - His absence from crypto and why he refrained during the boom in 2021 (01:10:33) - Thoughts about the opportunity set in FinTech today writ large (01:12:04) - Other potential opportunity sets beyond what’s already been discussed (01:13:39) - Lessons learned from his time spent with Marc Andreessen, Stan Druckenmiller, Henry Kravis, and David Geffen (01:21:59) - Balancing magnitudes of capital between investment funds  (01:23:32) - Why founders choose Thrive (01:29:15) - Vision as a key ingredient for founders (01:32:19) - His view of the investment industry in the world today writ large  (01:40:19) - Other investment firms he would invest in (01:42:48) - The kindest thing anyone has ever done for him

My guest today is Josh Kushner, founder and managing partner of venture firm, Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Thrive has gone from strength to strength since then and now manages $15 billion with a small team of 9 investors. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Josh rarely speaks in public about the firm and their philosophy so it was a blast to do this with him. Please enjoy my great conversation with Josh Kushner. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:14) - (First question) - Why do this podcast (00:06:14) - The development of taste and quality  (00:10:20) - CS Lewis tweet; The Inner Ring (00:11:53) - Founders being heroes and motivating quietly from the background (00:16:14) - Overview the founding story of Oscar Health (00:21:30) - Is a big business different from a small one (00:23:18) - Learning to identify good problems and creating a business to solve it  (00:25:43) - The birth story of Thrive Capital  (00:30:14) - Lessons learned from creating the first three Thrive funds (00:33:35) - Industry wide competition today and models for building a firm in general  (00:37:44) - Talent, recruiting and seeing potential in younger generations of people (00:45:40) - Investments he made during the early foundation of Thrive that had significant impact  (00:49:12) - His analogy for investing in early versus late stage (00:54:22) - The current macro environment (00:57:52) - Giving AI companies computing power instead of money (00:58:57) - Why he sold small stakes of Thrive  (01:03:10) - His philosophy on what makes a good product (01:05:20) - What he thinks about the models like Mobile and Cloud  (01:08:10) - His absence from crypto and why he refrained during the boom in 2021 (01:10:33) - Thoughts about the opportunity set in FinTech today writ large (01:12:04) - Other potential opportunity sets beyond what’s already been discussed (01:13:39) - Lessons learned from his time spent with Marc Andreessen, Stan Druckenmiller, Henry Kravis, and David Geffen (01:21:59) - Balancing magnitudes of capital between investment funds  (01:23:32) - Why founders choose Thrive (01:29:15) - Vision as a key ingredient for founders (01:32:19) - His view of the investment industry in the world today writ large  (01:40:19) - Other investment firms he would invest in (01:42:48) - The kindest thing anyone has ever done for him

My guest today is Jeremy Giffon. I spend all my time trying to find people who have some “singularity” to them. People who seem like they can do an N of 1 something. Having spent many days with Jeremy recently, he strikes me as one of those people. He was the first employee and general partner at private equity firm, Tiny, which buys and holds internet and technology focused businesses. Prior to that, he was on the founding team of MediaCore, which was acquired by Workday. The focus of our discussion is about esoteric opportunities that exist in private markets. How misaligned incentives and co-ordination problems create special situations for people like Jeremy to invest in. The rest of the conversation is wide-ranging and covers everything from compensation advice to meeting your heroes. Please enjoy my discussion with Jeremy Giffon. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:15) - (First question) - What defines the nature of a perfect business in his mind (00:05:21) - Key characteristics he’d look for in a perfect investment (00:09:58) - Coordination problems that excite him (00:14:02) - Raising funds and ghostship companies  (00:16:17) - Examples of a special situations transaction in private markets  (00:18:55) - Building up a sourcing mechanism (00:22:18) - The biggest mistakes he’s seen in buying and selling companies  (00:25:42) - Refining the underwriting process (00:28:57) - Thoughts about minimum rates of return and multiples on capital for the investments he makes  (00:30:44) - Being lazy enough to wait for good deals on enduring businesses  (00:33:32) - Why people do things they don’t like  (00:35:47) - Whether or not he feels like he knows what he wants in life (00:40:48) - Invest Like The Best - Kevin Kelly; The reward for good work is more work  (00:42:58) - Hiring CEOs (00:44:54) - Really good respective returns in low risk companies and why those opportunities continue to persist    (00:47:05) - Tactics for negotiating with and sourcing CEOs   (00:50:37) - Binaries - pre and post fall (00:55:58) - Being hard to kill (00:59:15) - His favorite interview question  (01:06:07) - Having an audience is incredibly underpriced  (01:10:13) - What else is significantly underpriced (01:12:14) - Things he feels are overpriced today writ large (01:15:54) - Criticisms of the cult of learning (01:20:21) - The one call that everyone needs to make  (01:27:18) - Meeting your heroes and having mentors  (01:30:48) - Notable differences between the business environments of Canada and the US (01:33:13) - Lessons learned from people he admires and models for seeing the world  (01:35:35) - Views he holds that would make people scratch their heads (01:40:02) - The kindest thing anyone has ever done for him 

My guest today is Dave Yuan. Dave is the Founder and Partner of Tidemark Capital, which he started in 2021 after 15 years as a General Partner at Technology Crossover Ventures. Dave has been investing in vertical market software as long as anyone I know and he currently sits on the board of two VMS businesses, Toast and Karbon. He is the perfect guest to deliver a primer on VMS, which is exactly what we do in this episode. Please enjoy my conversation with Dave Yuan. The Vertical SaaS Knowledge Project - Tidemark Capital Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here.  ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/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. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:57) - (First question) - Vertical Market Software (VMS) offers unique business models and customer benefits (00:04:02) - Industry-specific software serving SMBs with tailored functionality (00:06:53) - Assess market based on TAM, competition, and growth dynamics (00:10:00) - Trust as a nuanced factor in evaluating market opportunities (00:11:59) - Leverage account-based marketing and local network effects for VMS solutions (00:14:22) - Vertical solutions offer tailored value and quick results for specific industries (00:16:21) - Disrupting legacy control points through integration and surrounding functionality (00:19:07) - Building demand is crucial for small merchants (00:21:31) - VMS entrepreneurs need operational experience and multi-product mindset (00:23:13) - Investors need to adapt to the specific growth stage and market dynamics (00:25:22) - Gross retention is driven by control points, individual-based retention, and distribution (00:29:43) - Multi-product vertical SaaS: Integrated solutions for efficiency and value (00:32:33) - Diverse offerings to serve merchants' needs in a multi-product approach (00:34:07) - FareHarbor's unique strategy led to success in the tour industry (00:38:43) - LA-based company revolutionized commercial casting with a free software tool (00:40:03) - Opportunities remain in VMS, with greenfield areas and specific markets (00:45:12) - Key valuation considerations for VMS businesses (00:47:27) - Time horizon is crucial for investing in VMS businesses (00:48:04) - Businesses worth studying in this category (00:51:12) - The kindest thing anyone has ever done for him