HD in HD

• How Max Levchin Built the System Behind 90% of U.S. E-Commerce

  “Don’t just believe that things work, actually find out how they work and ask the question, can they work better?” This has been Max Levchin’s constant pursuit since childhood, leading him to build PayPal, HVF, and Affirm, a perfect example of where engineering meets entrepreneurship. In this episode, we explore what it takes to begin again after success and how Max Levchin’s relentless pursuit of optimization has defined two decades of fintech innovation. We also get into: • how a cryptography thesis became a fintech revolution, PayPal • the psychology of merging with Elon Musk’s X.com • why founders are idealists and investors are cynics • how Max measures success in human lives improved • and how America’s entrepreneurial DNA became its greatest competitive advantage This episode was recorded on October 24th, 2025. 00:00 Intro 12:28 The PayPal Story 32:30 Founder CEOs vs. Hired CEOs 43:49 Entrepreneurship 48:47 The Media Industry 55:53 Credit Card Debt in the US 01:06:03 Affirm's Business Model 01:09:01 Challenges and Ethics in Lending 01:24:31 AI and Underwriting Models 01:32:51 Crypto and Stablecoins 01:46:26 Closing Remarks ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD Connect with us here: 1. Max Levchin- https://x.com/mlevchin  2. Brex- https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugrasThis episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/

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• How Deliveroo Got Acquired by Doordash for $3.9B | Will Shu

  In a city built on great food, workers were still eating whatever was quickest. When Will Shu moved to London, he felt that disconnect firsthand and built Deliveroo to bridge it, transforming a local gap into a network spanning 10 markets. On this episode of HD in HD, Will shares how his belief in hard work and delayed reward helped him build Deliveroo into a global logistics leader, acquired by DoorDash for $3.9B. We also get into: • how they learned to manage riders, restaurants, and regulations  • how Deliveroo stood apart from competitors like Uber • what Will believes DoorDash and Deliveroo can learn from each other post-acquisition ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD Connect with us here: 1. Will Shu- https://x.com/WillShuRoo 2. Brex- https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth. 00:00 Intro 25:43 Will Shu's Early Life and Education 32:15 College Life and Career Beginnings 39:26 Wall Street Culture 46:15 The Birth of Deliveroo 01:04:58 Raising Funds 01:16:49 COVID-19 01:23:01 IPO and Market Reactions 01:36:54 AI and Future of Delivery

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• How Alex Bouaziz Built Deel Into a $17B Giant | Alex Bouaziz & Deel

  Global payroll is a maze most companies dread navigating. Deel turned it into their MOAT by streamlining HR across borders, powering remote work, and hitting a $1B+ run rate with over 5,000 employees. Alex Bouaziz, Deel’s CEO and co-founder, grew up nerding out on Nintendo and hunted perfection from Paris to MIT. His relentless curiosity built a platform that’s rewriting how the world hires. In this episode, we explore: • why he wakes up obsessed with your problems, not his product • how a Disneyland obsession shaped his entrepreneurial spark • why he’s doubling down on AI and stablecoins ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. Onward and upward, together. Connect with us: 1. Deel - https://x.com/deel 2. Brex - https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/ 00:00 Introduction 01:35 Being happy 02:50 Big family 11:56 Video games and math 14:59 Confidence 16:12 College and older people 23:47 America, Nintendo, Disney 26:08 MIT 26:59 Helping yourself, cold emails 31:51 PhDs are super lonely 34:38 Trying to impress 39:16 Brex 40:06 Deel 45:05 Gaming forums and money struggles 49:49 San Francisco, Tel Aviv, Paris 52:26 Remote work 54:32 Growth and value 1:00:42 Marketing and getting old 1:02:09 Next decade 1:04:07 Crypto 1:08:42 AI and payroll 1:12:00 Outro

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• How Adversity Made Him Unstoppable | Barry Diller

  How does someone with zero ambition rise to the top of Hollywood? Barry Diller started out as a ‘wayward’ kid with no plan, then took his first big risk in television by producing original TV movies, a gamble no one in Hollywood thought would work. In this episode, he shares how trusting his instincts and defying convention guided his journey from transforming Paramount to launching Fox Broadcasting Company and building IAC, now home to 10 publicly traded companies, leaving a lasting legacy. We also get into: • why adversity is the greatest training ground for instinct • what it took to launch Fox Broadcasting against three dominant networks • why sequels ruined Hollywood’s creative edge • spotting screen interactivity before the internet took over ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD Connect with us here: 1. Brex- https://x.com/brexHQ 2. Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth. 00:00 Intro 02:12 Barry Diller's Early Life 15:12 The ABC Network 25:30 Charles Bluhdorn 33:26 From TV to Paramount 42:34 Fox Broadcasting and Media Ventures 48:53 E-Commerce and Building IAC 59:07 Expedia

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• How Kalshi Sued the U.S. Government and Won | CEO Tarek Mansour

  When regulators tried to shut them down, Tarek Mansour took them to court, and made history. This week on HD in HD we're joined by the co-founder and CEO of Kalshi, the first fully regulated financial exchange for trading on events. He’s redefining how markets work by building a platform where people can trade on everything from elections to the economy, and proving that prediction markets can be both legitimate and transformative. In this episode, we also get into: why entrepreneurship has no clear destination, so you might as well enjoy the journey how trading shaped how he thinks about risk and decision-making how Kalshi survived its showdown with regulators the bet that event trading can make humanity more rational ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD Connect with us here: Tarek Mansour- https://x.com/mansourtarek_?lang=en Brex- https://x.com/brexHQ Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/ 00:00:00 Intro 00:01:13 Brex Sponsorship 00:02:11 Early Years in Lebanon 00:08:41 Success and Stress 00:29:23 Expected Outcomes and Variance 00:41:43 MIT Experience 00:45:59 Goldman Sachs 00:53:08 Y Combinator 01:00:48 Legal Challenges 01:08:14 Raising Funds 01:14:02 The Election Market Challenge 01:35:45 Winning the Lawsuit 01:40:25 Mainstream Success 01:44:01 The Role of Support Systems

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