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Invest Like the Best with Patrick O'Shaughnessy

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Invest Like the Best with Patrick O'Shaughnessy
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  • Joe Liemandt  - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]
    My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing from public view for two decades—only to emerge with a $1 billion bet that he can make kids learn 10x faster using AI. Joe has built an AI tutoring system so effective that students at his Alpha School literally beg not to take summer breaks, achieving 2x learning outcomes in just 2 hours with standardized test results that compete with the best of them. We dive deep into why this could be the most valuable product he's ever built, his contrarian thesis that traditional SaaS is facing AI-driven obsolescence, and how his experience buying 100+ software companies prepared him for this moonshot in a trillion-dollar market that hasn't innovated in 200 years.  For investors, this is a masterclass in deploying patient capital to rebuild broken systems from first principles, with insights on everything from regulatory moats to the intersection of AI and human psychology. As your excited skeptic, I push hard on the technology readiness, parental adoption hurdles, and whether this audacious vision can actually scale to a billion kids. Additionally, in a Colossus Profile released last week, our editor-in-chief Jeremy Stern reported, for the first time, Joe as the product guy behind Alpha School in a can’t miss piece of writing. And now please enjoy my conversation with Joe Liemandt.  Joe Liemandt’s Colossus Profile by Jeremy Stern. 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(00:06:08) How Alpha School Is Revolutionizing Learning(00:12:47) Personalized Tutoring with AI(00:19:59) Measuring the Impossible: 2x Learning Outcomes(00:25:39) All Educational Content Is Obsolete(00:35:51) Motivating Students: The Key to Success(00:42:06) Life Skills Workshops: Real-World Lessons(00:47:47) The Key to Happiness: High Standards(00:52:33) The Role of Guides and Coaches(00:58:22) Feedback Loops and AI in Education(01:04:20) The AI-Powered Classroom Experience(01:18:06) From Self-Doubt to Limitless Learning(01:28:20) Challenges in Public School Systems(01:41:56) Gamified Learning and Technology(01:49:46) From Trilogy to Trillion-Dollar Markets(01:55:05) Why Software Companies Fail(02:01:21) Trilogy University(02:10:39) Lessons from Mentors(02:17:25) Pushing Limits and Finding Passion(02:27:12) Joe's Kindest Thing
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  • Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]
    My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrophic skiing accident that left him in chronic pain for 18 years while simultaneously leading one of healthcare's most successful corporate turnarounds. His personal experience navigating his son's life-threatening cancer battle and his own medical challenges fundamentally changed his approach to healthcare, leading to innovations in employee welfare that Wall Street initially questioned but ultimately celebrated. During his tenure at Aetna, Mark generated 652% total shareholder return by implementing revolutionary employee policies and is now applying these lessons at Oscar Health to disrupt the $4 trillion healthcare industry with a technology-first approach. We discuss the power of servant leadership, employer-sponsored insurance vs individual choice-based plans, and the horizons of healthcare. Please enjoy this incredible conversation with Mark Bertolini. 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 (00:04:52) Mark's Ski Accident and Recovery (00:07:54) Early Life and Career Beginnings (00:12:51) Leadership Philosophy and Career Highlights (00:19:03) Healthcare System Insights and Innovations (00:25:31) Oscar Health: Current State and Future Vision (00:42:06) Personal Stories and Eastern Belief System (00:51:57) Discovering the Healing Power of Yoga (00:57:21) Transforming Employee Benefits and Wages (01:02:41) Personal Journey Through Chronic Pain (01:08:10) Reflections on Business Success and Leadership (01:15:54) Joining Bridgewater and Transitioning Leadership (01:22:47) Leading Oscar Health and Future Goals (01:34:12) Enduring Hardships and Finding Purpose (01:32:34) The Kindest Thing Anyone Has Ever Done For Mark
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  • Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437]
    My guest today is Peter Lacaillade. Peter is the Chief Investment Officer for Private Investments at SCS Financial and has built a notable private equity allocation platform within the wealth management industry. He shares his insights on how SCS's pooled vehicle structure has enabled them to compete with institutional giants, avoiding the adverse selection that plagues most wealth platforms. Peter shares his investment philosophy across lower middle market buyouts, emerging independent sponsors, and investing with what he believes to be category-defining managers. We discuss what separates high-quality private equity managers, the evolution of the industry toward AI-powered strategies, and private markets going mainstream. Please enjoy this conversation with Peter Lacaillade. 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. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). -- The views expressed reflect personal views of participants at the time of recording and not necessarily any third party and are subject to change.  The information provided is for informational and illustrative purposes only and does not constitute investment advice or an offer to buy or sell any securities. Assets under management is an estimate that reflects total assets managed and advised on. This recording contains certain forward-looking statements that reflect the participants’ current views. These statements are subject to many risks, uncertainties and factors which may cause future events to be materially different from these statements. Statements that reference past trends or activities should not be taken as a representation that such trends or activities will necessarily continue in the future. The investment strategies and any performance discussed are strictly intended to be for illustrative purposes only and are not meant to be representative of any entire investment program. Investments risk loss of capital and there is no guarantee that an investment will achieve its investment objective. Private investments in particular involve significant risks and are intended for experienced and sophisticated investors. -- Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:31) Advantages of Private Equity Over Public Markets (00:08:59) Talent Acquisition and Growth at SCS (00:10:28) SCS's Wealth Management Strategy (00:12:42) Trends in Private Equity (00:20:14) Challenges and Risks in Private Equity (00:26:06) The State of the Wealth Management Industry (00:35:07) Lower Middle Market Buyouts and Independent Sponsors (00:49:38) Introduction to Long Lake and Its Innovative Approach (00:54:26) The Rise of Holding Companies (00:57:03) Emerging Trends in Venture Capital 01:05:44) The Role of Endowments and Liquidity Solutions (01:10:40) Jake and Frank's Partnership (01:13:57) The Kindest Thing Anyone Has Ever Done For Peter
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  • Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]
    My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discuss his unique approach to distressed investing in the middle market, revealing how middle market EBITDA has declined 20-25% since 2019, creating what he calls the "K-shaped economy." His investment stories are legendary, particularly his $600+ million bet on NYC taxi medallions, which we go into in great detail. We discuss Marblegate’s approach to negotiation, sourcing deals directly from hundreds of regional banks, and understanding the human element in distressed situations. Please enjoy this conversation with Andrew Milgram. 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 (00:04:58) Understanding the K-Shaped Economy (00:07:08) Middle Market Challenges and Data Insights (00:16:56) Distressed Investing Explained (00:25:06) The Taxi Medallion Investment Story (00:46:46) Navigating New York's Taxi Medallion System (00:47:17) Building Relationships with Regulators and Unions (00:50:22) Taking the Taxi Operation Public (00:51:26) The Future of Autonomous Vehicles and Medallions (00:54:30) Investment Strategies and Risk Management (00:58:41) Negotiation Principles and Human Drama (01:11:55) Personal Reflections and Formative Experiences (01:17:22) The State of the American Economy (01:23:29) Insights on Private Credit and Equity Markets (01:30:39) Future of Asset Management (01:33:16) The Kindest Thing Anyone Has Done For Andrew
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  • Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435]
    My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's remarkable track record—including early investments in Rippling, Solana, and dozens of unicorns—but also the unconventional path he took to get there. From running a hedge fund straight out of high school to filing for bankruptcy at 24, then bootstrapping his way to building a $2 billion AUM venture firm using AngelList and relentless hustle. Our conversation begins in an unexpected place—the art world—where Ramtin has become a sophisticated collector, learning from mentors like Michael Ovitz about market dynamics that surprisingly mirror venture capital. We dive deep into how the art world actually works, and Ramtin explains how these lessons about "masterpieces" apply directly to identifying power-law companies in venture. We go deep on his approach to early-stage investing and how he built Abstract as a co-investment vehicle alongside firms like Sequoia, Benchmark, and Andreessen Horowitz. We explore his portfolio construction model, his philosophy on dilution-sensitive founders, and why he takes upwards of 30 pitch meetings per week to build his "frame of reference." We discuss why Abstract has the highest graduation rate from seed to Series A among all seed funds, and how this competitive advantage compounds over time. This is his first time telling his story, and we discuss the power of pattern recognition, relentless work ethic, and the unique opportunities available to those willing to start from scratch in Silicon Valley. Please enjoy this great conversation with Ramtin Naimi. Colossus Review Profile: Ramtin Naimi 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 (00:05:40) Learning from Mentors and Starting to Collect (00:08:50) Parallels Between Art and Venture Capital (00:12:57) Challenges in Art Collecting (00:20:45) The Role of Status in the Art World (00:25:00) Who Makes the Most Money in the Art World? (00:28:19) Abstract Ventures: Early Stage Investing (00:42:34) Starting a Venture Capital Firm from Scratch (00:43:12) Overcoming Bankruptcy and Early Struggles (00:50:34) Evaluating Technical Capabilities and Momentum (01:02:53) Competing for Deals and Building Relationships (01:15:25) The Role of Brand in Venture Capital (01:22:39) Early Life and Entrepreneurial Beginnings (01:28:40) Starting a Hedge Fund and Learning Hard Lessons (01:31:26) Transition to Venture Capital (01:37:19) Building Abstract and Family Life (01:52:03) The Kindest Thing Anyone Has Done For Ramtin
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About Invest Like the Best with Patrick O'Shaughnessy

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