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.

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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

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.

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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

 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

 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.

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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

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.

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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

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.

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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

Before we turn the page on 2024, we wanted to shine one more light on the man behind our most popular class of the last year. And that's Mitch Rales, co-founder of Danaher, one of the most impressive businesses to have been built anywhere in the world this past century. Having co-founded Danaher 40 years ago alongside his brother and best friend Steve, the Rales boys have strung together a track record of compounding that might even make Buffett blush. Consider that Danaher has annualized at over 21% for four decades, resulting in an 1800-times multiple on invested capital!

You’ll learn from Mitch about the key inputs to his outlier success: why greatness is a journey that takes an unusual time horizon, the role benchmarking plays in standing up any winning organization, why it is essential to cultivate learning agility and embrace transformational pivots over time, and also the qualities Mitch looks for both in the leaders and businesses he looks to support.

While Mitch is a natural teacher, this is actually his first recorded, long-form interview of any kind, and so we feel especially honored to share with you our candid conversation with someone who has shaped and transformed us and the business world in so many positive ways. Please enjoy today’s class with Mitch Rales.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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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 Art of Investing, visit joincolossus.com/episodes. 

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes

(00:00:00) - Welcome to Joys of Compounding

(00:04:32) - The Philosophy Behind Glenstone's Creation

(00:11:57) - Benchmarking and Continuous Improvement: Lessons from Danaher and Glenstone

(00:20:22) - The Influence of Mitch’s Father and Upbringing

(00:27:43) - Transforming Danaher During The George Sherman

(00:29:39) - Embracing Long-Term Vision and Patience

(00:35:47) - The Role of Leadership in Navigating Change

(00:41:21) - Danaher's Evolutionary Journey: From 1.0 to 4.0

(00:55:37) - Building a Culture of Internal Growth and External Innovation

(00:57:42) - The Art of Successful Acquisitions and Integration Strategies

(01:02:03) - Seeking Leadership Qualities and Business Traits for Long-Term Success

(01:05:14) - The Journey from Personal Experience to Philanthropy

(01:12:10) - Investment Philosophy: Concentration vs. Diversification

(01:28:46) - Operational Expertise as a Catalyst for Company Growth

(01:33:17) - Identifying and Supporting Talent in Business

(01:42:02) - The Impact of Secular Trends on Long-Term Investments

(01:48:53) - Revitalizing the Washington Commanders

(01:56:36) - Engaging with Fans and Building a Winning Culture

(02:04:16) - The Importance of Long-Term Vision

In honor of Notre Dame clinching a playoff spot, we're replaying our conversation from earlier this year with head coach Marcus Freeman. We discuss the power of relationships and how he talks with his players about the concepts of hard work & love. Marcus delves into what it takes to focus on inputs rather than outputs, especially as the college sports world is changing in unprecedented ways. 

And for you football fans out there, we even get into a little bit of what's ahead for Notre Dame’s program in Marcus’s third year as head coach. As alums and lifelong fans of the Irish, it was a real treat to host Coach Freeman at our studios. Please enjoy this class with Coach Marcus Freeman.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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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. This holiday season go to eightsleep.com/breakdowns and use code JOYS for up to $600 off the Pod 4 Ultra when bundled. 

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Art of Investing is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Art of Investing, visit joincolossus.com/episodes. 

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes

(00:00:00) - Welcome to Joys of Compounding 

(00:04:45) - Confidence and Leadership

(00:06:32) - The Profound Influence of Family

(00:10:39) - Embracing the Role of a Lifelong Learner

(00:12:43) - The Coaching Journey: From NFL Dreams to Notre Dame

(00:18:22) - Building Relationships: The Core of Coaching

(00:21:53) - Other-Centeredness as a Coaching Philosophy

(00:23:55) - The Mindset of Notre Dame Football

(00:24:59) - The Power of Relationships and Team Dynamics

(00:28:01) - Emphasizing Love and Choice in Team Culture

(00:30:37) - Continuous Improvement and Challenging the Status Quo

(00:35:17) - Navigating the Upheaval in College Football

(00:36:28) - The Importance of Education in Athlete Development

(00:39:04) - Family, Balance, and Being Present

(00:41:28) - Recruiting Talent and Building Teams at Notre Dame

(00:43:55) - Inspiring Today’s Youth and Upholding High Standards

Today’s teacher is renowned historian Patrick Griffin. Patrick is the former chair of the Department of History at the University of Notre Dame. In 2021, he was named the Harold Vivian Harmsworth Visiting Professor of American History at the University of Oxford, perhaps the highest honor an American historian can receive. 

He joined us to explore “The Lessons of History” by Will and Ariel Durant, a book that has been repeatedly recommended to us over the years by some of the world's most compelling investors, leaders, thinkers, and builders.

To quote the late great Charlie Munger, who was also a student of Durant, “There is no better teacher than history in determining the future.” This 100-page book is a masterful distillation of Durant's 11-volume 10,000-plus page magnum opus, “The Story of Civilization.”

Whether you're looking to develop better pattern recognition in your work, or perhaps more existentially how to begin to even think about how and what to paint on this precious canvas that we call a human life. We hope you enjoy this class on “The Lessons of History” with the esteemed Patrick Griffin.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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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. This holiday season go to eightsleep.com/breakdowns and use code JOYS for up to $600 off the Pod 4 Ultra when bundled. 

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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

(00:01:17) The Importance of History

(00:04:14) The Historian's Toolkit

(00:07:17) Will Durant's Journey

(00:09:18) Lessons from 'The Lessons of History'

(00:23:08) Human Nature and History

(00:34:29) The Role of Economy in History

(00:38:01) The American Revolution in Context

(00:38:20) The Irony of National Exceptionalism

(00:39:00) Revolutions and National Belonging

(00:42:17) Geography and the Age of Revolution

(00:43:50) Human Ingenuity and Overcoming Geography

(00:45:53) The Role of Common People in History

(00:47:12) The Immigrant Experience and Personal Reflections

(00:50:49) Yankee Sullivan: A Prizefighter's Tale

(00:55:55) Boxing as a Metaphor for Human Nature

(00:58:49) The Inevitability of War

(01:03:10) The Concept of Progress

(01:07:14) The Power of Compounding in History

Today's teacher is Rich Wong, general partner at renowned venture firm Accel. Rich is a very special investor and leader, and he spent many years as an operator prior to his time in VC. What was going to be a short stint as a venture operating partner nearly 20 years ago turned into a defining pivot for Rich.

He not only quickly reached the top of the venture profession but also became the go-to investor for many luminary companies, such as Atlassian, UiPath, AdMob, Checkr, Rovio, Service Channel, and many many more. 

His range of interests spans beyond venture, and he's very involved in many of the leading university-based poverty alleviation labs. It's always a treasure for us to find someone who integrates so many facets of life in service of others. Please enjoy our class with Rich Wong.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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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 the Joys of Compounding

(00:04:41) The Atlassian Chase Story

(00:07:41) Bootstrapping and Venture Capital

(00:18:10) Excel's Founding and Evolution

(00:22:14) Rich Wong's Early Influences

(00:24:42) Becoming an Accidental Venture Capitalist

(00:31:39) Excel's Team Dynamics and Investment Strategies

(00:38:28) The Evolution of Mobility and AI

(00:39:58) Bottom-Up Innovation and Defense Technology

(00:41:25) AI's Role in Incumbents vs. Startups

(00:44:53) Service Channel Case Study

(00:47:58) Capital Efficiency and Indigestion

(00:51:04) The Role of Grit and Overfunding

(00:55:29) Venture Capital Ecosystem and Returns

(01:04:03) Public Policy and Poverty Solutions

(01:11:43) Balancing Career and Personal Life

(01:15:37) How Rich Wants His Life To Be Measured