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Joys of Compounding

Colossus | Investing & Business Podcasts

This 'podclass' is a series of discussions with the world's best investors, company builders, academics, athletes, artists and human beings devoted to exploring the joys of compounding in all its forms.

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#41
Monday · 1 hr 32 min
Christian Harrison: From Overcoming a Lost Decade to U.S. Open Champion - [Joys of Compounding, EP. 41]
Our teacher today is Christian Harrison, the reigning Australian Open and US Open men’s doubles champion. Christian grew up in a tennis family, learning the game from his father and lifelong coach Pat alongside his older brother Ryan, and by 14 he was one of the top-ranked players in the world for his age. Then a misdiagnosed bone infection started a decade of setbacks that included eight major surgeries. What stands out is that he never lost his joy for the game, and that thread runs through the whole conversation. Rick and Christian talk about what his parents did to keep him going, why he played his first Grand Slam singles win at Wimbledon on a chipped heel bone, his pivot to doubles and grind back up through the Challenger circuit, the partnerships with Evan King and Neal Skupski that took him to two major titles, and how he handles success after so many years defined by adversity. Please enjoy class with Christian Harrison. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep. The new Pod 6 is a smart mattress cover that fits on any bed and automatically cools or warms each side through the night, with an AI called Autopilot that learns your sleep patterns and adjusts every night to help you get deeper, more restorative sleep. It has nine times the biometric sensors of the Pod 5, tracks heart rate at 99% accuracy compared to a standard ECG, reaches your set temperature 20% faster, and runs on a hub that's half the size and fits under most bed frames. No wearables required. The Pod 6 now starts at $1,999, the lowest starting price Eight Sleep has ever offered, and comes with a 30-day home trial and free returns. Go to https://www.eightsleep.com/joys and use code JOYS for up to $200 off. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Winning the US Open on home soil (00:03:45) Staying relaxed through a two-week tournament (00:05:41) Holding on to joy through doubt and injury (00:08:11) Parenting lessons from Pat and his mom, and midnight fishing trips (00:11:38) Earliest tennis memories in Shreveport(00:13:59) What drew him to the game (00:15:14) His grandfather’s legacy and the family work ethic (00:19:06) Specialization vs. generalization (00:20:54) Growing up a few steps behind his brother Ryan (00:22:13) Early heroes: Sampras and Hewitt (00:23:04) Moving the family from Louisiana to Texas to Bradenton (00:25:10) How the academy model is changing (00:28:26) What makes a father-son coaching relationship work (00:31:21) Why Pat had his sons play doubles as juniors(00:33:01) College tennis vs. turning pro (00:38:05) The first injury: a misdiagnosed bone infection (00:41:44) Nick Bollettieri’s role (00:45:33) Eight major surgeries, and what he’d do differently (00:50:15) Why comparison is negative (00:52:37) Wimbledon 2022 on a broken foot (00:57:05) What he’s learned from Novak Djokovic (01:00:41) How doubles differs from singles (01:03:04) Rebuilding through the Challenger circuit (01:04:24) Breaking through with Evan King (01:07:06) Partnering with Neal Skupski and winning the Australian Open (01:09:22) Why the first major is the hardest (01:11:00) Handling success as a Grand Slam champion (01:14:25) Training and recovery (01:16:01) How to improve your return of serve (01:19:05) Volleys and net play (01:20:08) What made the Bryan brothers so good (01:24:51) What he’s better at today than 10 years ago (01:25:57) How he defines success, and life after tennis
#40
October 7 · 1 hr
Luca Ferrari, Bending Spoons: Compounding Through Operational Excellence and Acquisitions - [Joys of Compounding, EP. 40]
Our teacher today is Luca Ferrari, co-founder and CEO of Bending Spoons. Luca spent more than a decade quietly building Bending Spoons in Italy into one of the best operators and acquirers of software businesses in the world, and we talk about why going slow early helped, how they hire people who act like owners, why they would happily buy shrinking companies at high returns, how AI lets small teams run big businesses, and what drives him to keep building. Please enjoy class with Luca Ferrari. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep. The new Pod 6 is a smart mattress cover that fits on any bed and automatically cools or warms each side through the night, with an AI called Autopilot that learns your sleep patterns and adjusts every night to help you get deeper, more restorative sleep. It has nine times the biometric sensors of the Pod 5, tracks heart rate at 99% accuracy compared to a standard ECG, reaches your set temperature 20% faster, and runs on a hub that's half the size and fits under most bed frames. No wearables required. The Pod 6 now starts at $1,999, the lowest starting price Eight Sleep has ever offered, and comes with a 30-day home trial and free returns. Go to https://www.eightsleep.com/joys and use code JOYS for up to $200 off. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:00:53) Becoming the Best Operator in the World (00:03:33) How Bending Spoons Measures Success (00:05:58) Why Bootstrapping Was an Advantage (00:10:30) Aiming for Something Massive (00:13:35) Delayed Gratification (00:14:53) Hiring for Extreme Ownership (00:20:08) Scaling Without Centralizing Decisions (00:25:03) How AI Changes the Work (00:27:23) Why They Buy Instead of Build (00:31:08) Why the Market Fixates on Organic Growth (00:33:31) Ignoring What the Market Likes (00:37:35) Happy to Buy Shrinking Companies (00:40:56) Avoiding the Law of Large Numbers (00:45:09) Reinventing Every Decade (00:49:42) Keeping Ownership as Teams Shrink (00:51:40) Finding the Right Shareholders (00:53:29) Why Going Public Helped (00:55:20) What Drives Luca
#39
September 17 · 1 hr 11 min
America at 250: The Ideas of 1776 - [Joys of Compounding, EP. 39]
Our teachers today are Frank Cogliano, Brendan McConville, and Patrick Griffin, three of the world's leading historians of the American Revolution and contributors to The American Revolution at 250, a new collection of essays Frank edited for UVA Press. Frank, Brendan, and Patrick compare the bicentennial they watched as kids in 1976 with the mood of 2026 and explain why almost nobody saw independence coming in 1774. They make the case that the Revolution succeeded because it paired Enlightenment optimism with a hard-eyed view of human nature, never promising a perfect republic, and they trace how committees built for resistance quietly became a government. They unpack what Dunmore's Proclamation did to the system of slavery, debate whether a country can hold together without its founding myths, and close with Frederick Douglass, a naturalization ceremony at Mount Vernon, and what gives each of them hope for America at 250. Please enjoy class with Frank, Brendan, and Patrick. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Get $500 off when you go to https://www.eightsleep.com/joys and get their biggest discount of the year. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:00:53) Episode Intro: America at 250 (00:02:06) A rare combination of humility, humor, and intellect (00:05:06) How the book came together and what 1976 felt like (00:09:45) Watching the tall ships from the Jersey City waterfront (00:16:00) A republic that never aimed for perfection (00:21:19) Jefferson has more faith in us than we have in ourselves (00:24:35) Bewilderment and living through history without knowing it (00:26:02) A golden age of understanding the Revolution's global impact (00:27:13) Was the Revolution inevitable? (00:31:50) How institutions built for resistance became a government (00:36:35) Dunmore's Proclamation and the disruption of slavery (00:44:43) Are founding myths necessary or dangerous? (00:49:37) Anyone can become an American (00:53:23) Holding the tension between ideals and failures (00:58:37) A Case for Redemption and Frederick Douglass (01:02:06) What gives you hope about America right now? (01:09:35) Closing thoughts
August 3 · 1 hr 27 min
A.J. Rohde: Living in the (Software) Limelight [Joys of Compounding, Ep. 38]
Our teacher today is A.J. Rohde, senior partner at Thoma Bravo, one of the largest software-focused private equity funds in the world. A.J. shares stories and lessons learned from his time investing in private equity - including why Thoma Bravo hires tennis players like him, and how playing in a band when he was younger helps make deals happen today. He talks through the fundamental disconnect between software company fundamentals and valuations in the market, and why he expects investors to reallocate toward SaaS when the AI trade cools off. Plus, why Thoma Bravo hires tennis players. Please enjoy class with A.J. Rohde. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by Portrait Analytics - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Use the code JOYS at for up to $350 off the Pod 5. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:03:24) Why Thoma Bravo Recruits Tennis Players (00:13:45) A Detroit Kid Finding His Sport (00:18:01) Drumming as an Outlet (00:26:08) The Spirit of Philadelphia (00:31:26) Complimenting a Blind Spot (00:35:32) Buying Licenses for Air (00:45:04) Constants Across Five Decades of Software (00:51:00) Underwriting a Ten-Year Hold (00:59:24) The Death of Playbooks (01:05:34) Data That Survives Hype Cycles (01:13:50) Proof of Resilience (01:22:01) How Range Makes a Better Investor
#37
June 29 · 1 hr 31 min
Nilam Ganenthiran: Building a Beacon in the Fog of AI - [Joys of Compounding, EP. 37]
Our teacher today is Nilam Ganenthiran, founder and CEO of Beacon, a centrally managed technology holding company that acquires the vertical software businesses serving the real economy. Nilam shares the immigrant story that shaped him and why trust becomes the scarce resource as AI turns competence into a commodity. He revisits the hard lessons of his eight years building Instacart, from leading in wartime to the morning Amazon bought Whole Foods. And he lays out the thesis behind Beacon, the bet that distribution and trust hold their value even as the cost of building technology falls, and why he sees a holding company as the right vessel to serve the parts of the economy that technology too often forgets. Please enjoy class with Nilam Ganenthiran. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Now through July 12th, get $500 off when you go to https://www.eightsleep.com/joys with Eight Sleep's Fourth of July sale and get their biggest discount of the year. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:04:38) Episode Intro: Nilam Ganenthiran (00:05:46) Why trust outlasts competence in the age of AI (00:07:48) From Kuala Lumpur to Canada (00:11:08) Why Canada (00:14:16) From grocery cashier to P&G to HBS (00:24:09) Parenting, serendipity, and the loss of free play (00:27:11) Joining Instacart and selling a vision (00:30:02) The hard lessons of eight years at Instacart (00:35:24) Leading in wartime (00:39:15) The day Amazon bought Whole Foods (00:45:08) Becoming the unlikely ambassador for an industry (00:47:05) Leaving Instacart and learning to invest at D1 (00:51:29) Building Beacon (01:00:15) Permanent capital (01:03:36) Building a founder-led team (01:10:02) Is software dead (01:14:03) The M&A machine and the operating system (01:19:50) The right tail and the blurring of software and services (01:24:22) Innovating with Main Street customers (01:29:33) Advice for the young and ambitious
#36
May 18 · 1 hr 17 min
Annalise Dragic & Zoe Zhao: Software Pioneers in the Dawn of AI - [Joys of Compounding, EP. 36]
Our teachers today are Annalise Dragic and Zoe Zhao, co-founders of Azlin Software, a next-generation serial acquirer of B2B vertical software companies focused on the providers of essential services and care for families. Annalise and Zoe share how their friendship evolved into a co-founding partnership, the 150 conversations with founders and investors that shaped Azlin from a blank page, and the four values they distilled into the acronym CARE. They explain why they chose family services as their first vertical, what culture-led and technology-led growth look like inside a company of companies, and the role of their AI agent Lumos in keeping the team intentionally lean. The conversation also covers their first acquisition of Fusemetrix, a UK software business serving leisure and attraction operators, the shareholder base they have assembled including Nic Humphries of HG Capital, Mitch Rales, and Will Thorndike, and the equity-efficient permanent capital structure they have designed to align every party for the long term. Please enjoy class with Annalise Dragic and Zoe Zhao. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Use the code JOYS at https://www.eightsleep.com/joys for up to $350 off the Pod 5. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:04:38) Episode Intro: Annalise and Zoe (00:06:00) Friends First, Co-Founders Second (00:07:45) How Annalise and Zoe Met (00:08:53) Should Co-Founders Be Similar or Complementary? (00:10:06) Tech & Investing Backgrounds (00:12:57) Annalise's Journey From LinkedIn to Investing (00:14:08) When Entrepreneurship Took Hold (00:16:29) Building With a Close Friend (00:18:33) Defining & Managing Burnout (00:20:46) Beyond the Resume (00:24:25) The Mentors Behind the Founders (00:27:34) The Nic Humphries Effect (00:29:34) Lessons From Visma (00:31:48) The Co-Founder Questionnaire (00:34:36) Why Choose B2B Software? (00:35:51) The 150-Person Benchmarking Exercise (00:37:14) Pioneering as Female Founders (00:39:25) The Name Behind Azlin (00:40:58) Azlin's Vision in Two Words (00:42:10) Why Acquire, Not Just Invest (00:45:40) What Makes a Great Target (00:46:16) The CARE Values (00:47:44) Investing in Family Services (00:51:28) Culture as a Multiplier (00:53:21) Building AI-Native From Day One (00:58:15) The Case for Equity Efficiency (01:02:49) When AI Isn't the Answer (01:04:58) Surprises From the AI Wave (01:06:52) Aligning Incentives for the Long-Term (01:11:35) Acquiring FuseMetrix (01:12:32) Life After the First Deal (01:14:27) The Levers of Compounding (01:17:24) A Compounder of Compounders
#35
April 27 · 1 hr 12 min
Justin Yoshimura - Resurrecting & Rolling Up Retail - [Joys of Compounding, EP. 35]
Our teacher today is Justin Yoshimura, founder and CEO of CSC Generation, a profitable commerce platform doing over a billion dollars in annual revenue across brands including Sur La Table, Backcountry, and One Kings Lane. As we explore what it takes to build an enduring company in a sector most investors have written off, we turn to Justin's unconventional path, one that challenges familiar assumptions about credentials, capital structure, and the future of retail. Justin shares how he stopped attending school around the age of sixteen and built his own curriculum through entrepreneurship, selling cell phones on eBay as a teenager before founding a loyalty program SaaS company that was acquired by Merkle in his early twenties. He describes the influences that shaped CSC's design, including a Warren Buffett obsessed father and the long term holding company model he watched David Williams build at Merkle, and explains why he rejected the traditional buy and flip playbook in favor of permanent ownership backed by patient, contrarian capital. This special session explores Justin's approach to acquiring retail brands in transition, the AI native operating system called Genesis that has turned loss making companies profitable within the first year of ownership, and the lessons he has carried through COVID, tariffs, and a decade of building a contrarian business in an industry many had written off. Please enjoy class with Justin Yoshimura. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Use the code JOYS at https://www.eightsleep.com/joys for up to $350 off the Pod 5. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:04:20) Episode Intro: Justin Yoshimura (00:07:02) Justin's Early Life and Childhood (00:10:20) Developing an Entrepreneurial Spirit (00:12:08) Building a Cell Phone Marketplace (00:14:39) Resilience as a Skill (00:16:26) Lessons from Y Combinator & Merkle (00:19:25) Why Choose Retail (00:22:12) Brands That Hit a Growth Wall (00:25:18) CSC's Founding Story (00:27:33) Direct Buy: CSC's First Deal (00:29:29) Justin's Fundraising Journey (00:32:15) Navigating the COVID Boom-Bust (00:36:19) Death by a Thousand Cuts in Retail (00:38:06) Competing for Deals (00:40:41) Lessons from the Tariff Shock (00:43:00) Backcountry Case Study (00:45:23) CSC's Genesis Platform (00:49:31) How AI is Changing Companies (00:52:01) Building an AI-First Culture (00:55:57) Hiring Well in the AI Era (00:58:09) Incentive Structures & Retention (01:01:40) Looking Ahead: CSC's Next Decade (01:05:08) Solving the Biggest Risk in Retail (01:08:30) The Decline of Search Traffic to Retailers (01:10:56) Closing Advice for Young People
#34
March 30 · 1 hr 40 min
Brent Beshore - Adventures in Permanent Equity - [Joys of Compounding, EP. 34]
Our teacher today is Brent Beshore, founder and CEO of Permanent Equity, a firm that backs family-owned businesses across North America with no intention of ever selling. As we explore what it means to build enduring companies and live a meaningful life, we turn to Brent’s unconventional path – one that challenges the core assumptions of modern private equity and the incentives that shape it. Brent shares how his background in liberal arts and early experiences with success led him to question the traditional models of achievement, wealth, and performance. He describes why he rejected the “buy, lever, and flip” playbook in favor of permanent ownership, and how designing the right incentives can protect against short-term thinking and misaligned behavior. This special session explores Brent’s journey from studying poverty and politics to building a different kind of investment firm, alongside deeper reflections on faith, introspection, relationships, and the pursuit of the good life. Please enjoy class with Brent Beshore. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Use the code JOYS at https://www.eightsleep.com/joys for up to $350 off the Pod 5. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, 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: ⁠@Buhrman_Rick⁠ | ⁠@PaulBuser⁠ | ⁠@colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:04:22) Washington & Lee and Finding Mentor Harlan Beckley (00:07:27) Liberal Arts Education in the AI Era (00:09:23) Why Brent Writes and Communicates Online (00:11:40) Being the Same Person Everywhere (00:15:29) Starting the 2025 Letter (00:16:46) Performance Culture and Almost Losing It All (00:18:23) God's Love vs. Performing for Approval (00:21:25) Building Permanent Equity (00:24:54) What is the Good Life? (00:26:56) Joy in Relationships Over Circumstances (00:29:43) Peace, Wholeness, and Lou Holtz on Happiness (00:32:28) Vacation Misery and the Performance Trap (00:34:58) Introspection vs. Rumination (00:37:51) Peter Kaufman's Influence and Compounding Ideas (00:42:31) Studying the Investment Greats (00:55:49) The Notre Dame Meeting That Changed Everything (00:59:36) Self-Education Through Reading and Study (01:09:39) Fee Structure: 2% vs. Performance-Based Incentives (01:13:16) Never Be a Forced Buyer or Seller (01:16:01) Building Your Own Investment Mosaic (01:19:15) Standing Out vs. Becoming a Commodity (01:21:09) AI Transformation in the Last 18 Months (01:24:14) Technology, Inequality, and Human Flourishing (01:28:26) Change Management and Upskilling Teams (01:31:34) Building Community at Main Street Summit (01:37:08) Tennis: From Childhood to Identity Transformation (01:42:40) Closing Reflections on Friendship
#33
Nov 24, 2025 · 1 hr 35 min
Julian Flannery - Building a Medical Miracle Factory - [Joys of Compounding, EP.33]
Our teacher today is Julian Flannery, co-founder and CEO of Summus, a company democratizing access to the world's leading doctors to drive better health outcomes and cost savings for employers and health plans. As we explore the future of human health, we turn to specialty care, where U.S. healthcare's spiraling costs, inadequate speed, and care disparities are most acute. Yet our system's greatest strength remains the expertise of our leading doctors—a national treasure that Summus was designed to connect with patients through an ecosystem of over 5,000 of the world's best physicians. This special session explores Julian’s fascinating journey from the White House and Morgan Stanley to pioneering the expert economy at GLG, and ultimately building what we can only describe as a miracle factory that's having an extraordinary impact on humanity. Please enjoy class with Julian Flannery For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ —-- This episode is brought to you by⁠ ⁠Portrait Analytics⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at⁠ ⁠portraitresearch.com⁠⁠ —-- 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 (00:02:09) Julian's Personal Healthcare Journey (00:02:41) Julian's Career and Leadership Insights (00:06:14) Julian's Early Life and Influences (00:13:18) Julian's College Years and Challenges (00:15:27) From the White House to Business School (00:22:03) Navigating the Business World (00:35:46) Building Summus: The Vision and Impact (00:42:51) Understanding the Healthcare System (00:49:42) Navigating Complex Healthcare Costs (00:50:44) Finding the Right Specialist (00:51:45) Building an Expert Marketplace (00:52:37) Challenges of Starting a Healthcare Startup (00:54:06) Trust and Expertise in Healthcare (00:56:02) How Summus Bridges Healthcare Gaps (00:58:32) The Role of Technology and Service (00:59:25) Creating a Doctor-First Culture (01:00:33) Summus' Impact on Employers and Employees (01:24:44) The Future of Healthcare and AI (01:29:04) Leadership and Building a Great Team (01:33:02) Personal Reflections and Gratitude
#32
Nov 12, 2025 · 1 hr 7 min
Matteo Franceschetti - The Sleep Maestro - [Joys of Compounding, EP.32]
Our teacher today is Matteo Franceschetti, co-founder and CEO of Eight Sleep, whose Pod technology ranks among the top five products that have meaningfully improved my quality of life. This conversation launches our series on founders and investors revolutionizing human health, covering everything from diagnostics to longevity science to biotechnology. Matteo's story is fascinating—he's an unlikely health tech founder who grew up in Italy pursuing law with little scientific or medical background, yet he's combined the discipline of an elite multi-sport athlete with the resilience of a serial entrepreneur to build a category-defining company. We discuss the challenges of building a consumer hardware company and how his team raised capital from world-renowned investors while achieving cash flow positivity to control their destiny. Please enjoy class with our friend Matteo Franceschetti. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ —-- This episode is brought to you by⁠ ⁠Portrait Analytics⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at⁠ ⁠portraitresearch.com⁠⁠ —-- 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) Meet Matteo Franceschetti: The Sleep Maestro (00:01:48) Matteo's Journey: From Italy to Health Tech (00:02:45) The Science and Impact of Sleep (00:05:57) Personal Stories and Early Ventures (00:15:23) From Law to Entrepreneurship (00:27:54) The Birth of Eight Sleep (00:32:20) Thought Partners and Business Ventures (00:32:42) The Importance of Sleep: Insights from Experts (00:34:29) The Evolution of Sleep Awareness (00:35:22) Innovating Sleep Technology (00:36:37) Building Eight Sleep: Challenges and Vision (00:40:04) Understanding Sleep Stages and Optimization (00:45:01) Balancing Execution and Vision in Business (00:47:39) Fundraising Journey and Lessons Learned (00:52:20) The Role of AI in Eight Sleep's Future (01:00:09) Future Ambitions and Product Roadmap
#31
Oct 13, 2025 · 1 hr 24 min
CHAPTERS Group - Building Europe's Next Software Champion - [Joys of Compounding, EP.31]
Our teacher today is Jan Mohr, CEO of Chapters Group, a publicly traded serial acquisition holding company with ambitions of becoming one of Europe's technology champions. Chapters' origins date back to a small software startup founded near Frankfurt in 1998. Twenty years later, the core business was sold to a strategic buyer, consolidating the market with the proceeds of the sale in 2018. With Jan's influence, the company embarked on a new chapter, pivoting to build the preferred home for mission-critical businesses across the old continent. Over the last five years, they have been on an absolute tear, having founded four distinct acquisition platforms that collectively acquired around 60 operating companies, demonstrated the ability to build a prolific M&A machine, while also improving the operations of the companies they acquire. Virtually every company in the world today is, on some level, thinking about AI in terms of threats, opportunities, and implications for their business. Perhaps nowhere is that discourse more animated right now than in the software industry. And as you'll hear from Jan, AI's potential to be a transformative force driving not only efficiencies, but also TAM expansion and most importantly, tangible customer value, is already evident throughout their business. We hope you enjoy class today with our good friend and Chapter CEO, Jan Mohr. For the full show notes, transcript, and links to mentioned content, check out the episode page here. —-- This episode is brought to you by ⁠Portrait Analytics⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at ⁠portraitresearch.com⁠ —-- 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 (00:04:48) The Rise of Artificial Intelligence (00:07:28) Jan's Vision for Chapters Group (00:12:01) The Importance of Talent and Co-Founders (00:15:48) Centralized Vision and Decentralized Operations (00:18:59) AI's Impact on Business Efficiency (00:27:42) AI in Public Sector and Enterprise (00:43:02) Mission Criticality and Public Sector Focus (00:45:57) Recruiting Talent for Clusters (00:48:11) Cybersecurity and AI Integration (00:50:09) European Market Dynamics (00:55:43) Deal Making vs. Deal Doing (01:14:11) Incentive Systems and Ownership (01:21:05) Future Vision and Talent Development
Oct 6, 2025 · 1 hr 22 min
David Senra - Lessons from the Founder Historian - [Joys of Compounding, REPLAY]
Today's teacher is ⁠David Senra⁠. David is an absolute force of nature who is taking the world by storm with his podcast "Founders." In class today, we enjoy access to the full spectrum of learnings from his decade-long study of history's greatest entrepreneurs, artists, athletes, and leaders. The library David built reflects a range of study that is boundless. From Alexander the Great to Catherine Graham to Alexander Graham Bell, from Warren to Jimmy Buffett, and from J. Gould all the way to Jay Z. He helps us gain an understanding of why virtually all of the greats in history devote themselves to the study of those that came before them. Please enjoy today's class with David Senra. 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 Joys of Compounding (00:05:23) Understanding the need to devote oneself to something (00:09:10) The profound and helpful insights gained from learning about historical figures (00:17:05) Advice for a 22-year-old about the value of relentless effort (00:27:14) Hard work as a prerequisite for achieving greatness (00:32:37) How time and effort influence the compound interest equation (00:41:34) Factors that hinder the pursuit of greatness (00:47:40) Seeking voices that guide you toward the right path (00:56:02) Curiosity as an innate talent or a cultivated skill (01:00:44) Letting go of interests that obstruct your goals (01:08:45) Striking a balance between work and family for a fulfilling life (01:14:50) Basic steps within our control to become the person we aspire to be (01:19:10) The unique appeal of podcasting as a business (01:24:19) Turning information from biographies into actionable knowledge.
#30
Sep 15, 2025 · 1 hr 24 min
Lessons from Steve Mandel - [Joys of Compounding, EP.30]
Our teacher today is Steve Mandel, founder of Lone Pine Capital, one of the defining investment firms of our time. For starters, Steve is, without question, among the most important leaders in the investment management industry. Consider that Seth Klarman once called him, “the best industry analyst I've ever met, who became the best long short hedge fund manager of his generation.” In our opinion, the magic of Lone Pine resides in the principles that form its foundation and the people that animate its culture. But to understand the organization, you really need to first understand its master builder, a man of unusual integrity whose reputation across every dimension of his life and at every chapter of his life is so consistent and compelling when it comes to investing. Steve has an infectious Buffett-like love for the craft, and he's someone who seems more rooted in an orientation of service than any investor we've ever met. And one of the great paradoxes of this story is that from day one, Steve deliberately architected Lone Pine so that it would always be about more than just him. Beyond Lone Pine, we also discuss the value of having heroes and mentors, how relationships can enrich an education and a career, the art of doing great research, and what is important when investing in periods of accelerated change. John Gardner once said, “There are men and women who make the world better just by being the kind of people they are.” It's truly an honor to bring this conversation to you with one of those kinds of people. Please enjoy class with the one and only Steve Mandel. 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 (00:02:15) The Evolution and Principles of Lone Pine Capital (00:05:15) Steve's Early Life and Influences (00:06:45) The Dartmouth Experience and Liberal Arts Education (00:09:07) Harvard Business School and Early Career Lessons (00:12:58) Mentorship and Learning from Industry Giants (00:17:28) Founding Lone Pine Capital: Vision and Business Plan (00:29:20) The Importance of Duration and Flexibility in Investing (00:37:57) Early Days of Lone Pine: Building a Lasting Culture (00:42:56) Retaining Talent: Key Factors (00:43:34) Evolving Leadership and Team Development (00:44:38) Portfolio Management Evolution (00:47:05) Cross-Functional Growth and Development (00:48:09) The Role of Analysts and Portfolio Managers (00:50:39) Adapting to Market Changes and Technology (00:54:04) Investment Strategies and Firm Philosophy (00:57:43) Challenges and Future Directions (01:08:45) Valuation and Investment Decisions (01:11:17) Mentorship and Analyst Development (01:20:07) Future Outlook
#29
Aug 25, 2025 · 1 hr 33 min
Back to School with Chris Begg! - [Joys of Compounding, EP.29]
We've got just the class to help you get back into that learning machine mode. We're stoked to be joined by our good friend Chris Begg, founder of East Coast Asset Management and adjunct Associate Professor at the Helibrunn Center for Graham and Dodd investing at Columbia Business School. He teaches security analysis, perhaps the most legendary investing course in higher education. In today's class, we offer some historical context on the legacy of the adjunct investing professor, addressing why the practitioner teacher has played such a formative role for so many of the world's greatest investors. We also share our own teaching journey and the curriculum and guests that have helped make our respective classes so impactful. We even include a preview of our brand new class at Notre Dame, Investing in the Good Life, which is in partnership with the Shedi Family Program in Economy, Enterprise, and Society, and the College of Arts and Letters. Please enjoy our Back to School Special with our friend and the dawn of compression, Chris Begg. 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 (00:03:23) Summer Highlights and Personal Reflections (00:08:24) Music and Podcasts: Inspirations and Reflections (00:16:43) The Art of Songwriting and AI (00:21:48) Season Two Reflections and Guest Highlights (00:33:18) The Legacy of Practitioner Teachers (00:48:00) Influential Teachers and Their Impact (00:50:24) Value Investing Principles and Classroom Dynamics (00:52:32) Personal Teaching Journeys and Early Influences (00:57:14) Memorable Teaching Experiences and Guest Lecturers (01:11:57) The Role of AI in Education (01:26:23) Future Plans and New Beginnings
#28
Jun 9, 2025 · 1 hr 28 min
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
May 27, 2025 · 1 hr 18 min
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
#27
Apr 21, 2025 · 1 hr 31 min
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
#26
Mar 24, 2025 · 1 hr 24 min
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
#25
Feb 24, 2025 · 40 min
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
#24
Jan 28, 2025 · 1 hr 22 min
Rich Wells - Keep Moving - [Joys of Compounding, EP.24]
This is Rick. Today's teacher is Rich Wells, managing director of Insight Partners, which celebrates its 30th anniversary this month. I've known Rich for 20 years since our time as section mates in business school, where he was consistently recognized as the smartest person in the room. Rich is universally regarded as one of the preeminent private market software investors of the last 20 years, helping drive Insight's success through agility and excellence. While achieving the highest heights in his career, Rich has also faced profound personal challenges, including the tragic loss of his wife Rachael. This vulnerable conversation offers critical wisdom about resilience and moving forward through life's darkest moments. No matter what life throws at you remember that you've got to find a way to keep going. Please enjoy class with my dear friend and software savant, Rich Wells. 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 (00:02:57) Meet Today's Teacher: Rich Wells (00:10:04) Early Career Challenges and Lessons (00:14:59) Joining Insight Partners (00:17:20) Reflecting on TCV and Moving to Business School (00:19:11) Experience at Business School and Joining Insight (00:26:05) Insight's Growth and Strategy (00:30:38) Evolution of Software and Investment Strategies (00:34:48) Impact of SaaS and Cloud on Software Development (00:36:41) Investment Philosophy and Market Insights (00:39:01) Empowerment and Team Dynamics (00:43:05) Majority Stakes and Mindset Shifts (00:45:14) Evolution from Value to Growth Investing (00:47:49) Shopify: A Generational Company (00:51:39) Expanding TAM: The Role of Payments (00:55:02) Personal Struggles and Triumphs (00:59:25) Rachel's Legacy and Life Lessons (01:10:06) Future of Software

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