Invest Like the Best 503n24

My guest today is John Zito. John is the Co-President of Apollo Global Management. He shares how they've quietly built one of the most important financial institutions of our time, originating over $250 billion annually. John's thesis on the convergence of private and public markets - and Apollo's positioning to capture 100% of client portfolios rather than just alternatives allocations - offers a fascinating glimpse into where institutional investing is heading. We discuss the cultural and strategic elements that drive John, Apollo’s merger with Athene, the idea of artistry at scale, and the evolution of capital markets. Please enjoy my conversation with John Zito.  For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠ here.⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠ Ramp⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠ Ramp.com/invest⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠ to learn more about the platform. –  This episode is brought to you by⁠⁠⁠ AlphaSense⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:55) The Rise of Apollo and Credit Markets (00:08:05) Innovations in Asset Management (00:11:42) The Role of the US in Global Capital Markets (00:15:26) The Future of Asset Management and Investment Strategies (00:21:03) The Impact of Interest Rates on Investment (00:25:27) Apollo's Business Model and Growth (00:25:17) The Changing Landscape of Private Markets (00:46:03) Apollo's Culture and Vision (00:47:54) The Importance of Company Culture (00:52:52) The Future of Private and Public Markets (00:57:50) Building a Great Origination Platform (01:02:03) Exciting Deals and Personal Stories (01:14:47) The Role of AI and Future Opportunities (01:22:16) Maintaining Company Culture Amidst Change (01:24:06) The Kindest Thing Anyone Has Ever Done For John

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. In the midst of her transition to OpenAI, we are spotlighting the force that is Fidji Simo. She is the former CEO of Instacart and grew up in a small town in the South of and was the first person in her family to graduate from high school. Since then, she has had a dazzling career with stops at ’s leading university, eBay, and Facebook. Fidji spent the better part of a decade at Facebook where she led the Facebook App before ing the online grocery platform, Instacart, in mid 2021. We talk about Fidji’s consumer product experiences, Instacart’s role within the grocery ecosystem, and delve into her personal philosophy on leadership. Please enjoy this wide-ranging discussion with Fidji Simo. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠WorkOS.com⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit colossus.com/episodes.  Stay up to date on all our podcasts by g 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 | @Colossus Show Notes (00:00:00) Welcome to Invest Like the Best (00:03:51) Comparing her experiences with Facebook and Instacart (00:06:22) The dimensionality of creating great consumer products online (00:07:50) How Instacart uses AI now and her advice to other companies who are ready to incorporate AI into their business (00:15:41) What being a pragmatic technologist means to her (00:18:02) Influences in younger years that led to her career path in technology (00:21:00) The landscape Instacart seeks to build and how major key players within the industry are involved (00:27:09) Data algorithms and their role in helping consumers (00:29:24) Scale around the original core business (00:32:12) The functional difference between Instacart shoppers and delivery drivers  (00:34:59) Issues with fully automated grocery store facilities (00:37:32) Insight into working with brands and consumer brand loyalty  (00:43:16) Her vision for the future of Instacart (00:46:58) The possibility of becoming the major software platform for most retailers (00:49:34) Her principles for capital allocation (00:52:34) Common misperceptions about Instacart from prospective investors (00:54:21) Her philosophy of seeing the magic in team (00:56:46) Expanding knowledge while managing a complex business environment   (01:01:01) When she felt the most helpless in her career (01:03:46) Insight into generative AI and how it could shape the online grocery experience (01:08:00) The role of content and its importance for businesses like Instacart (01:11:10) The future of AI personalities and customizing your shopping experience (01:12:35) The kindest thing anyone has ever done for her

My guest today is Graham Weaver. My guest today is Graham Weaver. Graham is the founder of Alpine Investors, a large private equity firm targeting an interesting market inefficiency. Alpine focuses on the thousands of $20 million revenue businesses whose baby boomer owners want to retire, but lack succession plans. Alpine buys companies and installs 28-year-old military veterans and top MBA graduates as CEOs, leveraging 25 years of intellectual property on how young executives can successfully run established businesses. Alpine's CEO-in-training program is now the most applied-to job at Harvard, Stanford, and Kellogg business schools. We discuss the past, present and future of their unique approach. Please enjoy my conversation with Graham Weaver. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠ here.⁠⁠ ----- This episode is brought to you by⁠⁠ Ramp⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠ Ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by⁠⁠ AlphaSense⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠ Alpha-Sense.com/Invest⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠ Ridgeline⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠ ridgelineapps.com⁠⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠https://thepodcastconsultant.com⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:13) The Journey to Private Equity (00:06:59) Early Influences and Personal Growth (00:09:54) The Power of Wrestling and Rowing (00:11:45) Choosing Your Path and Making Decisions (00:14:48) College Goals and Rowing Success (00:18:05) Lessons from Early Business Ventures (00:26:24) Founding Alpine and Early Challenges (00:34:46) Core Beliefs and Talent Development (00:39:07) Fun Board Meetings and Team Dynamics (00:40:42) Platform Building 101 (00:44:08) Talent and Training Programs (00:49:12) Employee and Customer Engagement (00:52:27) Financial Outcomes and Asymmetric Returns (00:55:52) Incentivizing Young CEOs (01:00:26) The Role of Emotional Intelligence (01:02:45) The Alpine CEO in Training Program (01:03:40) Teaching at Stanford and Influential Mentors (01:07:58) Helping Students Find Their ion (01:10:22) Visualizing Your Future Self (01:11:19) Scalability of Coaching (01:12:15) Personal Growth Through Teaching (01:16:16) The Role of Executive Coaching (01:24:45) Lessons from a Bad Deal (01:31:50) Daily Routines and Success (01:36:13) The Future of Private Equity (01:35:24) Unleashing Heroes at Alpine (01:38:09) The Journey of Building Alpine (01:41:31) The Kindest Thing Anyone Has Ever Done For Graham

My guest today is Gustav Söderström. Gustav is the Co-President, Chief Product Officer & Chief Technology Officer at Spotify. Gustav lets us behind the scenes on how Spotify thinks about the future of audio and video, and what leadership lessons he's learned from making mistakes and taking risks in a rapidly changing technological landscape. He shares fascinating insights on their synchronized team structure and how they have positioned themselves as "the R&D department" for the entire music industry. We discuss their integration of AI, their unique "bets board" process for allocating resources, and how they've evolved from a music service into a multimedia platform with over 650 million s. Please enjoy my conversation with Gustav Söderström. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ ----- This episode is brought to you by⁠ Ramp⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠ Ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by⁠ AlphaSense⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠ Alpha-Sense.com/Invest⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠ Ridgeline⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠ ridgelineapps.com⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:27) Spotify's Journey Through Technological Shifts (00:06:28) The Impact of Generative AI on Consumer Products (00:09:36) AI in Coding and Productivity (00:11:11) Consumer Engagement and AI Playlisting (00:14:43) Strategic Frameworks and Decision-Making at Spotify (00:19:39) The Bets Process: Structured Innovation (00:31:11) The Future of AI and Business Models (00:44:31) The Future of AI and Inference Costs (00:46:21) The Concept of Computronium and Infinite Computing (00:47:02) David Deutsch and the Beginning of Infinity (00:48:55) The Power of Explanations and Human Understanding (00:54:03) Spotify's Free Tier and Consumer Needs (00:56:45) Spotify's Relationship with the Music Industry (01:03:03) The Rise of Podcasting and Audiobooks (01:15:45) Personal Interests and Continuous Learning (01:20:32) The Kindest Thing Anyone Has Ever Done For Gustav

Today, we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of ⁠50X⁠ Season Two – a series from Will Thorndike and the team at Compounding Labs, in partnership with Colossus.  This episode is the first in a series of three on Asurion, the world’s leading tech care company with more than 300 million customers. In an interview with Co-Founder and Chairman ⁠Kevin Taweel⁠, we explore Asurion’s scrappy origins in roadside assistance, acquisitive entry into handset insurance, contentious capital allocation decisions, and much more.   In each episode of 50X, we look in detail at an investment that has appreciated at least 50-fold. From the seat of the professional investor and occasionally the CEO, we explore its origins, evolution, and eventual outcome, studying key themes around long-term value creation ranging from operations, capital allocation, and culture to pivotal buy and sell decisions. To enhance the quality and depth of our interviews, we rigorously study each asset in advance, diving into all available public and private resources. Make sure to subscribe to ⁠⁠50X⁠⁠ in your preferred podcast player.⁠   For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠ here.⁠ —- This episode is brought to you by⁠⁠ Ramp⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠ Ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. — This episode is brought to you by⁠ ⁠System Six⁠⁠, a searcher-owned outsourced bookkeeping and ing services firm that has been a great partner to us at Compounding Labs.  With the right modern tools and a strong team, System Six will eliminate headaches for you and give you time back so you can focus on growing your business. Whether you're a CEO or CFO stuck in the weeds, or an investor trying to your CEOs and portfolio companies, reach out to [email protected] and mention the podcast for your first month of ongoing bookkeeping free. —- 50X is a property of Colossus, LLC. For more episodes of 50X, visit⁠ colossus.com/episodes⁠. Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠). Follow us on Twitter: @50Xpodcast | @colossus Show Notes (00:00:00) Welcome to 50X (00:01:59) Sponsorship: Ramp (00:03:16) Sponsorship: System Six (00:04:24) Introduction to Kevin and Asurion (00:05:55) Kevin’s Background Pre-Asurion (00:13:31) Origin of Kevin’s Search Fund (00:19:51) Acquiring Road Rescue (00:28:03) Operating Road Rescue (00:39:21) Early Success: Hold or Sell — a Critical Early Decision? (00:44:51) Entry into Handset Insurance: Acquiring the Merrimac Group (00:52:31) Vertical Integration (00:58:31) Capital Allocation in the Search Fund Period (01:02:31) TA Investment

My guests today are Rick Ruback and Royce Yudkoff. Rick and Royce are Harvard Business School professors who teach their students how to search for, acquire, and run small business directly after graduation. It has been almost a decade since our first conversation, and unlike many past interviews that have become outdated due to technology or market changes, the core principles they shared about entrepreneurship through acquisition remain remarkably relevant today. They explore fascinating developments in the search-fund ecosystem, including the bifurcation between funded searchers targeting larger companies and self-funded entrepreneurs finding success with smaller businesses. Rick and Royce share their accumulated wisdom on what makes a company worth buying, why the "magic is in the multiples," and how their students consistently achieve impressive returns through patient, value-oriented business acquisition. Please enjoy my conversation with Rick Ruback and Royce Yudkoff. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ ----- This episode is brought to you by⁠ Ramp⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠ Ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by⁠ AlphaSense⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠ Alpha-Sense.com/Invest⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠ Ridgeline⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠ ridgelineapps.com⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:23) Changes in the Small Firm Acquisition Space (00:06:52) The Impact of SBA Loans on Acquisition Entrepreneurship (00:08:55) The Evolution of Entrepreneurship Through Acquisition (00:10:09) Risk and Return in the Search Fund Model (00:13:38) The Role of Investors in Funded and Unfunded Searches (00:19:33) Criteria for a Good Acquisition Target (00:28:36) The Growing Popularity of Self-Funded Searches (00:43:21) Challenges and Red Flags in Small Firm Acquisitions (00:49:47) Exploring Margin Expansion and Growth (00:51:02) The Impact of Practical Teaching in Business Education (00:52:12) Keys to a Successful Business Class (00:53:30) The Role of Theory in Practical Business Education (00:55:29) Challenges and Rewards of Teaching Business (00:57:46) Capital Allocation in Small Businesses (01:00:50) Advice for Aspiring Business Searchers (01:03:45) Value Creation and Business Lifecycle (01:08:20) Deciding to Leave Private Equity (01:11:20) The Future of Higher Education in Business (01:16:06) Ongoing Relationships with Former Students (01:18:45) Favorite Business Cases to Teach (01:24:46) Encouraging More People to Pursue Business Ownership

My guest today is David Senra. David is the host of Founders podcast and a dear friend. This is our third time doing Invest Like the Best together and we have conversations like this one all the time. In today’s episode, David distills wisdom from 400 entrepreneur biographies into a single word: focus. He reveals why exceptional builders like Todd Graves and James Dyson create billion-dollar empires through obsessive dedication to simple ideas—whether perfecting chicken fingers or deg vacuum cleaners—while rejecting conventional growth timelines and investor pressure. David challenges us all to find the one thing we’d pursue even without recognition or reward, or what I like to call your life’s work. We discuss the concept of “anti-business,” raising capital as a founder, and decades-long commitment. Please enjoy this discussion with David Senra.  For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:43) The Essence of Focus in Entrepreneurship (00:09:20) The Value of Long-Term Commitment (00:17:41) The Importance of Simplicity and Mastery (00:37:11) The Miracle of Entrepreneurship (00:44:56) James Dyson's Journey to Success (00:47:03) The Importance of ion in Business (00:49:12) Critique of Modern Consumerism (00:52:18) The Value of Craftsmanship (00:56:36) The Drive for Excellence (01:04:06) The Importance of Hiring Top Talent (01:09:54) Creative Financing Strategies (01:19:35) Defining a Founder

My guest today is Cliff Sosin. Cliff is the founder of CAS Investment Partners, a fund he started with $5 million in 2012 and has grown to $1.7 billion as of the last reported numbers at the end of 2024. At the time, CAS had only four positions. This conversation is different to our typical episodes. We start by talking about Cliff's investing philosophy but the bulk of this long discussion is a case study into his remarkable investment in Carvana. Cliff is one of the biggest investors in the business, which had a market cap over $60 billion in 2021, then fell 99%, survived, and now has a market cap approaching $50 billion again. While I hosted Carvana's CEO, Ernie Garcia, last year to get the inside perspective on managing through such turbulence, today we hear the investor's side of this extraordinary story. It is a singular episode and there are so many lessons in this rare opportunity to hear a major investor describe his decision-making process at every stage of the journey. Please enjoy my great conversation with Cliff Sosin. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. –  This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:00:32) Early Career and Discovering Investing (00:01:18) Journey Through Financial Firms (00:01:49) Starting the Firm and Initial Challenges (00:03:41) Investment Philosophy and Market Realities (00:05:07) Building the Firm and Investor Relations (00:07:23) Defining a Good Business (00:12:31) Contained vs. Uncontained Businesses (00:15:30) Mental Models and Market Insights (00:30:13) The Role of ESG in Investing (00:34:26) The Carvana Investment Story (00:41:01) The Complexity of Car Transactions (00:41:43) Carvana's Real Estate and Logistics Network (00:44:12) Reconditioning and Selling Cars (00:45:16) Carvana's Financing and Customer Service (00:46:43) Economies of Scale and Trust (00:49:40) Challenges and Management Insights (00:59:07) Operational Issues and Market Challenges (01:18:56) Questioning Carvana's Sales Strategy (01:19:17) The Role of Word of Mouth in Carvana's Growth (01:20:28) Identifying Early Adopters (01:21:00) The Impact of Market Conditions on Carvana (01:22:10) Carvana's Operational Challenges (01:23:10) Cutting Costs and Organizational Efficiency (01:27:19) The Apollo Deal and Debt Restructuring (01:28:23) Personal Reflections on Investment Decisions (01:34:21) The Psychological Toll of Investment (01:45:16) Future Investment Strategies and AI (01:49:48)The US Market and Investment Opportunities (01:54:51) The Kindest Thing Anyone Has Ever Done For Cliff

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. There aren't many people like Cyan Banister. Her life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke. Yet, in spite of everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel investors of this era, having invested early in SpaceX, Uber, Postmates, and Deepmind to name a few winners. She became the first female investing partner at Peter Thiel’s Founders Fund and now invests at Long Journey Ventures. Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits. It is also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this great conversation with Cyan Banister. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit colossus.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 g 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 | @Colossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: [00:00:00] Welcome to Invest Like the Best [00:04:06] Contrarian Thinking in Investing [00:05:30] ing Founders Fund and Learning from Peter Thiel [00:11:15] Investing in Companies that Change Lives [00:14:00] The Importance of Overcoming Adversity for Founders [00:16:02] Personal Journey and Choosing Hope [00:20:56] Embracing Curiosity and Wonder in the Face of Adversity [00:21:20] Reconnecting with Our Inner Child [00:24:46] The Interruption and Resumption of the Conversation [00:27:20] The Power of Intuition in Business Decisions [00:32:28] The Story Behind the Investment in Uber [00:38:46] Conclusion: Following the White Rabbit of Curiosity [00:39:08] Investing in Uber: The Beginning [00:41:50] The Impact of Success: Personal Wealth and Privacy [00:50:22] The Intersection of Spirituality and Investing [00:59:34] The Bill Murray Experience: A Lesson in Presence [01:09:54] The Violin Kid: A Tale of Curiosity and Generosity [01:12:43] The Evolution of Investing: A Personal Journey [01:16:34] The Philosophy of Giving: The Universe's Return [01:17:36] The Spirit of a Venture Firm: Founders Fund [01:23:09] The Power of Integral Family Systems [01:28:41] The Trillion Dollar Question: Disrupting Hollywood [01:36:05] The Future of Artistry: AI and Creativity [01:41:39] The Power of Kindness

My guest today is Matt Huang, co-founder of Paradigm, a leading crypto investment firm with over $12 billion in assets under management. Before launching Paradigm in 2018 with Coinbase co-founder Fred Ehrsam, Matt was a partner at Sequoia Capital, where he led many of the firm's crypto investments. It’s widely reported that Michael Moritz called Matt “the only regrettable loss in Sequoia’s history.” In our conversation, Matt shares his framework for navigating the often illegible frontier of crypto, how his early investment in ByteDance (now worth 10,000x his initial capital) shaped his approach to identifying exceptional founders, and why he believes so deeply in crypto’s long-term potential. His firm, Paradigm, not only invests in many of the leading companies in the industry, it also builds open-source tools used by most of crypto. Matt has a rare blend of IQ and EQ that allows him to understand technical complexity, bring together unique talents, and ride out crypto’s notorious volatility. Whether you're crypto-curious or crypto-skeptical, I think you'll find his perspective valuable. Please enjoy my great conversation with Matt Huang. Matt Huang's Profile in Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. –  This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:15) Matt Huang's Early Life and Career (00:08:13) College Years and Early Career (00:12:27) The Failed Startup and Lessons Learned (00:25:58) The Journey to Sequoia Capital (00:32:51) Discovering Bitcoin and Crypto (00:39:33) Founding Paradigm (00:45:40) Building a Unique Investment Team (00:46:37) The Role of Engineers and Researchers (00:48:03) Challenges and Volatility in Crypto (00:52:11) The FTX Investment and Its Aftermath (00:58:40) Crypto as a New Financial System (01:05:19) The Importance of Stablecoins (01:09:54) AI and Crypto: The Next Frontier (01:16:19) Personal Motivations and Mission (01:29:23) The Role of Regulation in Crypto (01:32:27) The Kindest Thing Anyone Has Ever Done for Matt

Today's guest is Neil Mehta, founder of Greenoaks Capital. In 2012, aged 27, Neil left D.E. Shaw to start Greenoaks with his friend Benny Peretz. One of their first investments was in Coupang, a South Korean e-commerce company led by founder Bom Kim. Neil was so convinced of Coupang's potential that he invested 40% of their initial $50 million fund into the company—a bet that eventually returned about $8 billion. Over its first 13 years, Greenoaks has backed legendary companies like Figma, Wiz, Carvana, Stripe, Discord, Rippling, and Toast—generating over $13 billion in gross profits with a 33% net IRR. Henry Kravis, one of Neil's early investors, describes him as "extremely disciplined" with "exceptional timing" who has "gone against the tide many times." Greenoaks operates with remarkable concentration: just 55 core companies across nearly $15 billion in assets, managed by only nine investment professionals. Their approach reflects their singular pursuit: finding companies that will become a meaningful part of the S&P 500. In our wide-ranging conversation, Neil shares this mission along with his framework for identifying exceptional founders, his concept of "jaw-dropping customer experiences," and how his grandfather's gun shop in India shaped his appreciation for builders of all kinds. Please enjoy my excellent conversation with Neil Mehta. Neil Mehta's Profile in Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. –  This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:32) Connecting Craftsmanship to Career (00:07:45) The Concept of Jaw Dropping Customer Experience (JDCE) (00:09:48) Building a Successful Business: The Coupang Case Study (00:17:26) The Importance of Founders & Business Models (00:30:05) Greenoaks' Unique Approach to Venture Capital (00:37:54) A Memorable Encounter with Henry Kravis (00:40:52) Early Career and Lessons from Hong Kong (00:44:53) The Partnership with Benny (00:50:28) Navigating the Competitive Landscape (00:59:14) High Conviction Investments: TripActions, Rippling, and Carvana (01:07:00) Investment Strategy and Company Evaluation (01:13:23) Adventures in Emerging Markets (01:17:09) Challenges and Lessons Learned (01:26:16) Personal Values and Community Impact (01:32:16) The Kindest Thing Anyone Has Ever Done For Neil

My guest today is Michael Ovitz. Michael is the legendary talent agent and Co-Founder of CAA or Creative Artists Agency and he is ing me on Invest Like the Best for a second time. Michael started CAA in 1975 and over the next 20 years, he built it into the world's most formidable talent agency, changing Hollywood forever. He shares insights into how he identifies exceptional people across diverse fields - from Hollywood directors like Steven Spielberg to tech founders like Alex Karp of Palantir and venture capitalists like Marc Andreessen. Michael is a force whose expertise extends beyond just people, as he has also become a master in creating institutional momentum, which you’ll hear in his involvement with the MoMA, Gulfstream, and more. We discuss his "pilot's checklist" for evaluating talent, the importance of time as his most valuable resource, and why he believes maintaining excellence is critical in any field. Please enjoy my conversation with Michael Ovitz. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. –  This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:56) Spotting Talent and Building Institutions (00:08:01) The MoMA Story: Transforming an Art Institution (00:19:35) The Importance of Relationships and Time (00:24:32) Building Successful Boards and Teams (00:34:02) Insights on Leadership and Momentum (00:44:49) Building Blackstone and CAA (00:56:32) The Power of Momentum (00:57:25) Overcoming Fear of Failure (01:01:52) Strategic Partnerships and Global Influence (01:17:32) The Importance of Excellence (01:18:22) Mentorship and Legacy (01:34:00) The Future of Media and Technology (01:41:36) Pursuit of Happiness and Lifelong Learning

My guest today is Darren Farber. Darren is a Managing Partner of Albion River, a private direct investment firm focused on acquiring companies that produce highly technical Defense Products & Services. He is a Former special advisor to the Deputy Under Secretary of Defense, a Former member of U.S. Department of Defense Task Force for Business and Stability Operations, and the list goes on and on. Darren is a wealth of knowledge in this space and someone I am grateful to have in the US corner. He shares his perspective on the changing role of the U.S. in global defense and how recent conflicts have shaped military technology and strategy. Darren explains his investment approach at Albion, focused on finding "one-of-one" suppliers and getting as close to the fundamental "molecules" as possible in defense technology. We discuss insights on evaluating the Taiwan situation, the lessons from Ukraine, how the defense budget is allocated, what investors can learn from defense primes, and why technological superiority remains America's greatest advantage. Please enjoy this discussion with Darren Farber.  Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. –  This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Introduction and Show Overview (00:06:23) The Changing Role of the US in Global Defense (00:09:23) Evaluating Defense Budgets and Spending (00:11:41) Commercial Technology in Defense (00:15:37) Challenges and Innovations in Defense Procurement (00:22:36) US Defense Strategy and Global Order (00:37:34) The Future of Warfare (00:42:13) Lessons from the Gaza Contingency (00:44:44) Challenges in Defense Venture Capital (00:47:36) The Importance of Responsible Parties in Defense (00:51:06) Industrial Capacity and Defense Investments (00:53:49) Lessons from US Defense Primes (00:59:48) Supply and Demand in Defense Markets (01:07:34) The Role of Net-Centric Warfare (01:10:33) Hopes and Fears for the Future of Kinetic Warfare (01:14:42) The Kindest Thing Anyone Ever Did For Darren

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. This is a rare opportunity to hear from one of the best investors of the past decade—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. 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. Please enjoy my great conversation with Josh Kushner. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by WorkOS. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit WorkOS.com to Transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by through. through streamlines subscription documents, KYC, and AML compliance, so you can focus on running your fund, not managing paperwork. New SEC Update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again. You'll need continuous monitoring of your investors and all their beneficial owners across multiple watchlists, plus a comprehensive anti money laundering program. through has already processed 50,000 LPs and built the complete solution. Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit through.com to get compliant now. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit colossus.com/episodes.  Follow us on Twitter: @patrick_oshag | @Colossus Show Notes (00:00:00) Welcome to Invest Like the Best (00:05:14) Why do this podcast (00:08:14) The development of taste and quality  (00:12:20) CS Lewis tweet; The Inner Ring (00:18:14) Overview the founding story of Oscar Health (00:25:18) Learning to identify good problems and creating a business to solve it (00:27:43) The birth story of Thrive Capital (00:32:14) Lessons learned from creating the first three Thrive funds (00:39:44) Talent, recruiting and seeing potential in younger generations of people (00:47:40) Investments he made during the early foundation of Thrive that had significant impact (00:51:12) His analogy for investing in early versus late stage and styles of real estate investing (00:56:22) The current macro environment (01:00:57) Why he sold small stakes of Thrive (01:05:10) His philosophy on what makes a good product (01:10:10) His absence from crypto and why he refrained during the boom in 2021 (01:12:33) Thoughts about the opportunity set in FinTech today writ large (01:15:39) Lessons learned from his time spent with Marc Andreessen (01:17:43) Lessons learned from Stan Druckenmiller, Henry Kravis, and David Geffen (01:22:09) Firm values he thinks are very important (01:31:15) Vision as a key ingredient for founders (01:34:19) His view of the investment industry in the world today writ large  (01:44:48) The kindest thing anyone has ever done for him

My guest today is Gili Raanan. Gili is the founder of Cyberstarts, a VC firm focused on cybersecurity and the world’s first VC that is majorly backed by cyber entrepreneurs. Cyberstarts’ $50 million dollar first fund exploded to close to $2 billion in just three years. Gili describes cybersecurity today as "the perfect storm" where global conflicts and AI advancements are creating unprecedented threats. He talks about Cyberstarts' "Sunrise" methodology, which uniquely identifies customer pain points before building solutions. We discuss a focus on finding resilient talent, overcoming personal adversity, the evolution of the cybersecurity landscape, and Google's recent acquisition of Wiz, as Cyberstarts was one of Wiz's earliest investors. Please enjoy my discussion with Gili Raanan. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:52) AI's Impact on Cybersecurity (00:07:51) Offensive and Defensive Tactics (00:09:32) The Future of Cybersecurity (00:15:42) The First Fund: A Legendary Success (00:17:36) Building a Successful Cybersecurity Company (00:28:24) The Sunrise Methodology (00:31:58) Reversing the Startup Process (00:32:53) The Sunrise Methodology (00:33:17) Identifying Market Pain Points (00:34:57) The Importance of Customer Actions (00:36:58) From Conversations to Software Development (00:38:57) The Role of Simulations in Startup Success (00:40:12) Fundraising and Valuation Strategies (00:42:08) Pricing and Market Dynamics (00:46:16) The Value of Superpowers in Founders (00:50:10) Google’s Acquisition of Wiz (01:07:24) Personal Resilience and Tragedy (01:10:30) Future of Cybersecurity and AI (01:12:25) The Kindest Thing Anyone Has Done For Gili

My guest today is Alex Wiltschko. Alex is the founder and CEO of Osmo, a science and technology company giving computers a sense of smell. He set out on a mission to digitize our sense of smell and he describes how Osmo is teaching computers to both read and write scent. Alex was kind enough to walk me through the laboratory which you can watch in the video version of this interview on Youtube and Spotify, where he demonstrates their method to the madness. We discuss their first commercial application, Generation, which is revolutionizing the fragrance industry by dramatically accelerating the typically years-long process of custom scent creation. We discuss all of the potential business implications this technology unlocks, applications ranging from counterfeit detection to health monitoring, and creating a cutting-edge proprietary platform in a historically routine industry. Please enjoy my conversation with Alex Wiltschko. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:25) Introduction to Plum 1.0 (00:06:20) Synthetic Chemistry & OI (00:07:09) Perfumer's Organ & Fragrance Creation (00:08:03) Launching Generation Fragrance House (00:09:15) The Fragrance Design Process (00:12:04) AI and Olfactory Intelligence (00:14:59) The GCMS Machine (00:22:08) The Scent Printer (00:26:47) The Journey of a Fragrance Enthusiast (00:30:47) The Unsolved Problem of Scent (00:32:45) Applying AI to the World of Scent (00:33:17) Validating AI Predictions with Double-Blind Trials (00:39:42) The Emotional Power of Scent (00:49:01) Challenges & Future Prospects (00:59:08) The Defining Moment: Digitizing Smell (01:00:41) The Kindest Thing Anyone Has Ever Done For Alex

My guest today is Kelly Granat. Kelly is the Co-Chief Investment Officer and Managing Director at Lone Pine Capital, one of the most storied and successful hedge fund and investment firms of the last several decades. We explore how investing has evolved since Kelly ed the industry and she shares insights into Lone Pine maintaining its edge through deep fundamental research and a collaborative culture. We discuss what makes great businesses and great investments, how leadership can transform companies, and Kelly’s perspective on evaluating management teams and identifying opportunities around corporate change that the market often misprices. Please enjoy my conversation with Kelly Granat. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Learn About Ramp, Alphasense, & Ridgeline (00:06:09) Market Structure Evolution (00:08:39)The Impact of ive Investing (00:10:21) Collaboration & Team Dynamics (00:13:48) Excitement in Periods of Extreme Change (00:14:21) The Role of Competition & Curiosity (00:22:00) Fundamental Research & Data Integration (00:27:34) Investment Philosophy (00:35:31) People-Centric Investing (00:42:24) Succession Planning (00:49:32) Facing the Pressure of Early Success (00:50:31) Burnout & Rediscovery (00:57:08) Learning from Industry Leaders (00:58:04) Evaluating Talent and Competition (01:11:29) Lessons in Investment (01:27:27) The Kindest Thing Anyone Has Ever Done For Kelly 

Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413] My guest today is Devon Zuegel. Devon is the founder and president of the Esmerelda Institute, and she is creating a new town called Esmerelda in California wine country. Learning of Devon and her plan, I couldn’t help but wonder why there aren’t more people building new towns. She shares the origin story of her project Esmeralda, a modern reinvention of the Chautauqua community she cherished growing up, and we explore her fascinating work building communities and reimaging how we live together. We discuss how environments fundamentally shape human behavior, how cost of space impacts creativity, the financial challenges of town-building despite their potential for strong returns, and the plans in place for Esmerelda. Please enjoy this fascinating conversation with Devon Zuegel.  Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Learn About Ramp, Ridgeline, & Alphasense (00:06:00) The Origin of Devon's Obsession with Places (00:08:07) Proximity and Cost of Space (00:10:02) The Chautauqua Inspiration (00:11:31) Building a New Town: Esmeralda (00:13:23) Urban Design and Street Importance (00:15:44) Community Values and Peer-to-Peer Learning (00:18:15) Edge Esmeralda: A Prototype Community (00:21:38) Challenges and Trust Building in Development (00:26:45) The Role of Cars in Urban Planning (00:31:10) Mortgages and Taxes: Shaping Communities (00:42:11) Devon's Journey: From Stanford Review to Esmeralda (00:43:41) Tools for Thought and Loops (00:46:33) Urban Design and Pop-Up Villages (00:50:06) Exploring Las Catalinas and Car-Free Living (00:52:31) Placemaking and Organic City Development (00:56:25) Frontier Camp and Creating Collaborative Spaces (01:02:39) Building New Towns: Financial and Infrastructure Challenges (01:12:05) The Kindest Thing Anyone Has Done For Devon

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. There's nobody I've met quite like Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. I listen to this at least once a year. I hope you enjoy it. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by through. through streamlines subscription documents, KYC, and AML compliance, so you can focus on running your fund, not managing paperwork. New SEC Update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again. You'll need continuous monitoring of your investors and all their beneficial owners across multiple watchlists, plus a comprehensive anti money laundering program. through has already processed 50,000 LPs and built the complete solution. Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit through.com to get compliant now. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit colossus.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 g 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 | @Colossus Show Notes [00:00:00] Welcome to Invest Like the Best [00:05:21] What Don Valentine’s heart was like [00:08:30] The most productive and unproductive parts of Don’s toughness  [00:12:55] Why it’s so important to understand someone’s core motivations [00:18:44] The most formative experiences he had prior to becoming an investor that impacted his investing the most  [00:22:37] What venture looks like to him today relative to his prior career [00:28:37] Whether or not he’d go into venture today if he was in his late 20s  [00:34:10] Helping companies circumnavigate mediocre positioning  [00:39:15] How interacting with companies early on has changed over the ears [00:43:12] Whether or not new entrants into venture should build firms with enterprise value  [00:48:14] Sussing out the killer gene in somebody  [00:51:04] How successful people can instill the lessons learned from hardship into their children  [00:54:30] Whether or not competitive advantage can be architected ahead of time when building a company   [00:57:21] The early 2000s clawback at Sequoia and what navigating that period was like  [01:01:06] What he’s learned about picking the right LPs and partnering with them [01:04:18] Making sure that performance is on everyone’s minds all the time  [01:09:59] The kindest thing anyone has ever done for him

My guest today is Chris Pedregal. Chris is the founder and CEO of Granola, an AI-powered notepad that transcribes your meetings and enhances your meeting notes. Chris shares fascinating insights on how humans have historically developed tools to extend our cognitive capabilities - from writing and mathematical notation to data visualization - and how AI represents the next frontier in this evolution. We explore competitive dynamics between model providers and application builders, and Chris shares his vision for AI tools that make us "more human and better humans" rather than replacing human altogether. Our conversation covers the product philosophy behind Granola, the challenges of building in the fast-moving AI space, and how small teams are creating outsized impact in this new paradigm. Please enjoy my conversation with Chris Pedregal. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Learn About Ramp, Ridgeline, & AlphaSense (00:05:41) Historical Examples of Tools for Thought (00:06:55) The Impact of AI on Tools for Thought (00:09:08) Introducing Granola: AI-Powered Notetaking (00:10:10) Granola's Unique Approach to AI Notetaking (00:13:33) Experiences and Future Vision (00:15:40) Privacy and Social Norms in AI Recording (00:20:47) Building Granola: Challenges and Innovations (00:34:55) AI Startups and Granola's Early Adoption (00:35:40) Unexpected from High-Profile CEOs (00:39:53) Building Better and Faster in a Competitive Space (00:42:09) The Future of AI-Powered Workspaces (00:54:00) Challenges and Opportunities in AI and Education (00:56:03) The Evolution of App Development (00:58:01) The Potential of Small Teams in Big Businesses