Joys of Compounding

• Will Thorndike - Lessons from the Eternal Outsider - [Joys of Compounding, EP.28]

  Our teacher today is Will Thorndike, co-founder of Compounding Labs and author of the acclaimed book, “The Outsiders.” In our opinion, Will has emerged as one of the most influential and innovative investor minds of the past few decades. And if you care about long-term value creation and the art of capital allocation, chances are you've also benefited from some of his ideas.  In 1994, he founded Housatonic Partners, a pioneering private equity firm known for its unusually long holding periods and its leadership in the search fund space alongside his mentor and Stanford professor Irv Grousbeck. Will helped to originate the modern search fund model, backing early career CEOs to buy and grow businesses with long-term horizons and radically aligned incentives. Since then, he has invested in the majority of the top 20 search fund outcomes to date, including Asurion, which he recently profiled on his podcast 50X.  We explore Will's full arc from the research that led to “The Outsiders” to his decades as an investor to the new frontier he's now helping to shape. We talk about what makes a business truly enduring, why great leadership and resource allocation remain so misunderstood, and how the right people, structure, and alignment enable companies to compound over time. Please enjoy this class with Will Thorndike. For the full show notes, transcript, and links to mentioned content, check out the episode page here. —-- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit joincolossus.com/episodes.  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Follow us on Twitter: @Buhrman_Rick  | @PaulBuser | @JoinColossus Show Notes (00:00:00) Welcome to The Joys of Compounding (00:00:57) Introducing Will Thorndike (00:03:35) The Rise of Long Duration Serial Acquisition Holding Companies (00:07:25) The 50X Podcast Journey (00:16:29) The Origins of Will's Investing Career (00:18:11) Stanford's Influence and Key Mentors (00:23:48) The Search Fund Model Explained (00:39:18) The Outsiders: From Concept to Acclaim (00:46:33) The Influence of Leverage and Share Buybacks (00:47:30) Personal Reflections on the Book's Impact (00:52:54) Experiments in Public Markets: CNX and Perimeter (00:58:35) The Evolution of Inorganic Growth Models (01:02:52) The Power of Long-Term Ownership (01:14:52) The Importance of Relationships and Learning

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• Katie Koch - Be A Force Multiplier - [Joys of Compounding, REPLAY]

  Our teacher today is Katie Koch. Katie is the President and CEO of the TCW Group, a storied firm with over 200 billion in assets under management and a fascinating 50-year legacy as a pioneer in the investment industry. Katie just took the TCW reins in 2023 after more than 20 years at Goldman Sachs. She joined Goldman right after college as the self-proclaimed least capable person in the firm and rose to become chief investment officer of their 300-billion-dollar public equity business.  Please enjoy our class with the wonderful force multiplier, Katie Koch. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Art of Investing, 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: @ArtofInvest | @Buhrman_Rick  | @PaulBuser | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes (00:00:00) Welcome to Art of Investing (00:02:38) First Question - ‘What Choice Would You Make If You Knew You Would Not Fail?’ (00:05:00) Katie's Childhood and Lessons from Parents (00:13:24) Her Experience at the University of Notre Dame (00:24:15) Katie's 20-Year Career at Goldman Sachs (00:36:16) The Importance of Mentorship and Sponsorship (00:41:18) Building Meaningful Relationships for Career Growth (00:43:24) The Transition from Goldman to TCW (00:48:15) The Importance of Humility and Collaboration in Leadership (01:01:35) The Significance of Diversity in Investment Firms (01:07:30) The Role of a CEO and Building a Successful Team (01:10:42) Transitioning from Investor to Operational Leadership (01:12:06) Differentiating an Investment Organization (01:15:59) Balancing Family and Career

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  1:18:51
• Sebastian Mejia - Scaling With Soul - [Joys of Compounding, EP.27]

  Our teacher today is Sebastian Mejia. He combines intellectual range with emotional depth and is the co-founder of Rappi, the on-demand delivery platform that has become one of Latin America's most influential tech companies.  In this episode, we discuss resilience, identity, intuition, and building companies with a sense of urgency and wonder. We will go from Sebastian’s immigrant hustle in New York to billion-user ambitions in India, from early-stage chaos to the challenge of scaling a tech company across hundreds of Latin American cities. Now, Sebastian is entering a new chapter, one that blends investing with company building. He's been asking bigger, more personal questions like what's enduring, what's authentic, and where can I bring my full self to the table? Please enjoy our class with Sebastian Mejia. For the full show notes, transcript, and links to mentioned content, check out the episode page here. —-- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit joincolossus.com/episodes.  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Follow us on Twitter: @Buhrman_Rick  | @PaulBuser | @JoinColossus Show Notes (00:00:00) Welcome to The Joys of Compounding (00:01:22) Sebastian's Early Life and Influences (00:11:15) The Turning Point: Loss and Resilience (00:17:06) Adventures in Spain and Beyond (00:36:52) Building Rappi: From Concept to Reality (00:46:06) Building a Multicultural Team (00:53:30) The Intersection of Operating and Investing (01:01:43) Building Tako: A Payroll Infrastructure Company (01:06:46) The Impact of AI on Business (01:17:45) Balancing Speed and Quality in Startups (01:21:10) Zeal: Integrating Interests and Talents (01:28:20) The Importance of Kindness and Purpose

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  1:31:21
• Chad Cascarilla - Blockchain’s Carpenter - [Joys of Compounding, EP.26]

  Our teacher today is Chad Cascarilla, co founder and CEO of Paxos, the leading regulated blockchain infrastructure company that is reimagining a complete technological replatforming of our global financial markets. Paxos aims to democratize finance by enabling instant global asset movement, partnering with industry leaders like PayPal, Stripe, MasterCard, and others. For those confused by crypto speculation, Chad offers a grounded perspective on blockchain's potential to solve fundamental financial system problems—informed by his experience as an early Bitcoin adopter who started buying at just three cents. This conversation was a ton of fun for us, mainly because Chad is one of the most fascinating and compelling people we've had the privilege of knowing and learning from.He's a highly introspective, integrated, and ridiculously well read thinker and someone who just gets a lot of stuff done. He's a skeptic and a dreamer, a rigorous research analyst and a visionary builde, an aspiring mystic and an absolute animal. Please enjoy our conversation with Chad Cascarilla.  For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by EightSleep, the temperature-controlled mattress cover that heats or cools your mattress to transform your sleep. The Pod 4 Ultra is the new gold standard in intelligent sleep systems. It can be added to your current mattress like a fitted sheet and is been clinically proven to give you up to an hour more quality of sleep every night. The cooling capability can cool your side of the bed to 20 degrees below room temperature, all managed by the pod's autopilot feature, which adjusts the temperature throughout the night. Go to eightsleep.com/joys for $350 off.  —-- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit joincolossus.com/episodes.  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Follow us on Twitter: @Buhrman_Rick  | @PaulBuser | @JoinColossus Show Notes (00:00:00) Welcome to Joys of Compounding (00:05:32) Chad's Early Life and Career (00:09:50) The Journey to Notre Dame (00:19:45) The Path to Wall Street (00:27:16) Launching Cedar Hill (00:35:30) Navigating the Financial Crisis (00:46:35) Notable Companies and the Origin of Paxos (00:48:34) Creating Liberty City Ventures (00:54:55) Challenges in Financial Services (00:59:21) The Promise of Blockchain (01:10:59) Regulatory Landscape and Future Prospects (01:21:51) Advice for Consumers, Companies, and Investors

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  1:24:16
• Jacqui Morby - The Queen Of Software - [Joys of Compounding, EP.25]

  Today’s teacher is Jacqueline Morby. She may well be the greatest investor you've probably never heard of. For anyone who invests in software or participates in the now nearly trillion dollar global growth equity industry, chances are Jackie helped to shape and give rise to the professional world you inhabit. In 1978 at the age of 40, and with her only professional experience to date being a few years of substitute teaching, Jackie joined TA Associates, the largest venture capital firm in the world at that time. Within just a few years, she would revolutionize her industry, effectively originating the concept of cold calling profitable bootstrap technology companies not actively looking for funding. While the concept seems so simple, this truly was a radical innovation and in effect pioneering the art of looking for talented people in companies that don't necessarily want to be found, sparking a movement that created what we now know as growth equity. As if that's not enough, Jackie was also one of the very first investors of any kind to recognize the inherent business quality of software companies. Over the next two decades, as software would begin to eat more and more of the world, Jackie would have a front row seat as one of the most important capital partners to the industry. This is Jackie's first podcast of any kind, and we feel so honored to bring this conversation to you, mainly because hers is a story that merits so much more attention. Please enjoy this class with the queen of software, Jacqui Morby. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by EightSleep, the temperature-controlled mattress cover that heats or cools your mattress to transform your sleep. The Pod 4 Ultra is the new gold standard in intelligent sleep systems. It can be added to your current mattress like a fitted sheet and is been clinically proven to give you up to an hour more quality of sleep every night. The cooling capability can cool your side of the bed to 20 degrees below room temperature, all managed by the pod's autopilot feature, which adjusts the temperature throughout the night. Go to eightsleep.com/joys for $350 off.  —-- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit joincolossus.com/episodes.  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Follow us on Twitter: @Buhrman_Rick  | @PaulBuser | @JoinColossus Show Notes (00:00:00) Learn About EightSleep (00:05:00) Introduction to Jacqueline Morby: The Queen of Software (00:06:35) Early Life and Education (00:07:44) Jacqui’s Family Life and Early Career (00:11:04) Joining TA Associates and Industry Innovations (00:13:13) Early Days at TA Associates (00:15:17) Impact of Teaching and Overseas Experience (00:16:52) Pioneering Cold Calling in Venture Capital (00:19:05) Cold Calling Success Stories (00:23:17) Missed Opportunities and Big Wins (00:25:45) Investing in Software: A Revolutionary Idea (00:40:07) Philanthropy and Cure Alzheimer’s Fund

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