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- Yesterday1h 17m
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 Fusemetrics, a UK software business serving leisure and attraction operators, the shareholder base they have assembled including Nick Humphreys of HG Capital, Mitch Rails, 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 Welcome to Joys of Compounding Episode Intro: Annalise and Zoe Friends First, Co-Founders Second How Annalise and Zoe Met Should Co-Founders Be Similar or Complementary? Tech & Investing Backgrounds Annalise's Journey From LinkedIn to Investing When Entrepreneurship Took Hold Building With a Close Friend Defining & Managing Burnout Beyond the Resume The Mentors Behind the Founders The Nic Humphries Effect Lessons From Visma The Co-Founder Questionnaire Why Choose B2B Software? The 150-Person Benchmarking Exercise Pioneering as Female Founders The Name Behind Azlin Azlin's Vision in Two Words Why Acquire, Not Just Invest What Makes a Great Target The CARE Values Investing in Family Services Culture as a Multiplier Building AI-Native From Day One The Case for Equity Efficiency When AI Isn't the Answer Surprises From the AI Wave Aligning Incentives for the Long-Term Acquiring Fuse Metrics Life After the First Deal The Levers of Compounding A Compounder of Compounders
- 3 weeks ago1h 12m
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 Welcome to Joys of Compounding Episode Intro: Justin Yoshimura Justin's Early Life and Childhood Developing an Entrepreneurial Spirit Building a Cell Phone Marketplace Resilience as a Skill Lessons from Y Combinator & Merkle Why Choose Retail Brands That Hit a Growth Wall CSC's Founding Story Direct Buy: CSC's First Deal Justin's Fundraising Journey Navigating the COVID Boom-Bust Death by a Thousand Cuts in Retail Competing for Deals Lessons from the Tariff Shock Backcountry Case Study CSC's Genesis Platform How AI is Changing Companies Building an AI-First Culture Hiring Well in the AI Era Incentive Structures & Retention Looking Ahead: CSC's Next Decade Solving the Biggest Risk in Retail The Decline of Search Traffic to Retailers Closing Advice for Young People
- Mar 30, 20261h 40m
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 Welcome to Joys of Compounding Washington & Lee and Finding Mentor Harlan Beckley Liberal Arts Education in the AI Era Why Brent Writes and Communicates Online Being the Same Person Everywhere Starting the 2025 Letter Performance Culture and Almost Losing It All God's Love vs. Performing for Approval Building Permanent Equity What is the Good Life? Joy in Relationships Over Circumstances Peace, Wholeness, and Lou Holtz on Happiness Vacation Misery and the Performance Trap Introspection vs. Rumination Peter Kaufman's Influence and Compounding Ideas Studying the Investment Greats The Notre Dame Meeting That Changed Everything Self-Education Through Reading and Study Fee Structure: 2% vs. Performance-Based Incentives Never Be a Forced Buyer or Seller Building Your Own Investment Mosaic Standing Out vs. Becoming a Commodity AI Transformation in the Last 18 Months Technology, Inequality, and Human Flourishing Change Management and Upskilling Teams Building Community at Main Street Summit Tennis: From Childhood to Identity Transformation Closing Reflections on Friendship
- Nov 24, 20251h 35m
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 Welcome to Joys of Compounding Julian's Personal Healthcare Journey Julian's Career and Leadership Insights Julian's Early Life and Influences Julian's College Years and Challenges From the White House to Business School Navigating the Business World Building Summus: The Vision and Impact Understanding the Healthcare System Navigating Complex Healthcare Costs Finding the Right Specialist Building an Expert Marketplace Challenges of Starting a Healthcare Startup Trust and Expertise in Healthcare How Summus Bridges Healthcare Gaps The Role of Technology and Service Creating a Doctor-First Culture Summus' Impact on Employers and Employees The Future of Healthcare and AI Leadership and Building a Great Team Personal Reflections and Gratitude
- Nov 12, 20251h 7m
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 Welcome to The Joys of Compounding Meet Matteo Franceschetti: The Sleep Maestro Matteo's Journey: From Italy to Health Tech The Science and Impact of Sleep Personal Stories and Early Ventures From Law to Entrepreneurship The Birth of Eight Sleep Thought Partners and Business Ventures The Importance of Sleep: Insights from Experts The Evolution of Sleep Awareness Innovating Sleep Technology Building Eight Sleep: Challenges and Vision Understanding Sleep Stages and Optimization Balancing Execution and Vision in Business Fundraising Journey and Lessons Learned The Role of AI in Eight Sleep's Future Future Ambitions and Product Roadmap
- Oct 13, 20251h 24m
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 Welcome to The Joys of Compounding The Rise of Artificial Intelligence Jan's Vision for Chapters Group The Importance of Talent and Co-Founders Centralized Vision and Decentralized Operations AI's Impact on Business Efficiency AI in Public Sector and Enterprise Mission Criticality and Public Sector Focus Recruiting Talent for Clusters Cybersecurity and AI Integration European Market Dynamics Deal Making vs. Deal Doing Incentive Systems and Ownership Future Vision and Talent Development
- Oct 6, 20251h 22m
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 Welcome to Joys of Compounding Understanding the need to devote oneself to something The profound and helpful insights gained from learning about historical figures Advice for a 22-year-old about the value of relentless effort Hard work as a prerequisite for achieving greatness How time and effort influence the compound interest equation Factors that hinder the pursuit of greatness Seeking voices that guide you toward the right path Curiosity as an innate talent or a cultivated skill Letting go of interests that obstruct your goals Striking a balance between work and family for a fulfilling life Basic steps within our control to become the person we aspire to be The unique appeal of podcasting as a business Turning information from biographies into actionable knowledge.
- Sep 15, 20251h 24m
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 Welcome to the Joys of Compounding The Evolution and Principles of Lone Pine Capital Steve's Early Life and Influences The Dartmouth Experience and Liberal Arts Education Harvard Business School and Early Career Lessons Mentorship and Learning from Industry Giants Founding Lone Pine Capital: Vision and Business Plan The Importance of Duration and Flexibility in Investing Early Days of Lone Pine: Building a Lasting Culture Retaining Talent: Key Factors Evolving Leadership and Team Development Portfolio Management Evolution Cross-Functional Growth and Development The Role of Analysts and Portfolio Managers Adapting to Market Changes and Technology Investment Strategies and Firm Philosophy Challenges and Future Directions Valuation and Investment Decisions Mentorship and Analyst Development Future Outlook
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About Joys of Compounding
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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