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• Why Airwallex Is Betting Against SWIFT and Stripe | CEO Jack Zhang

  Jack Zhang landed in Melbourne at 15 with no money, no English, and no one to lean on. By 30, he was turning down a billion-dollar offer from Stripe. In this episode of HD in HD, I sit down with the co-founder and CEO of Airwallex to trace his zero-to-borderless journey—from small-town China to building one of the biggest tech stories ever to come out of Australia. We get into: • What Airwallex did differently that Stripe couldn’t in APAC • The $100,000 mistake that nearly derailed their first client • How Jack handled 2022’s valuation reset (and why he didn’t panic) • The AI opportunity he thinks everyone is sleeping on • how Airwallex hit $1B in volume before raising a proper Series A 00:00 Trailer 00:46 Introduction 01:18 Airwallex 04:58 No English from China to Australia 15:15 My first business, no financial support 23:06 All work, no fun 31:03 Development and coffee 36:26 Nothing is that hard 40:05 Startups 45:40 Brex 46:29 Starting Airwallex 53:27 The whole thing fell apart 57:20 Sequoia Capital and Tencent 1:05:41 Billion-dollar acquisition offer 1:11:59 Managing globally 1:16:20 Motivation and efficiency 1:23:26 Worth billions, hard to turn 1:24:58 Lessons from China 1:29:38 Outro

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• From Iranian Refugee to Uber CEO | Dara Khosrowshahi

  When Uber needed a reset, only a disciplined leader could see the path forward. Raised in one of Iran’s leading industrial families, Dara Khosrowshahi watched everything disappear during the revolution as his family rebuilt their lives in the U.S. In this episode, he shares how, with education as the only constant, he rose to become the youngest VP at Allen & Co., played a defining role across IAC and Expedia, and ultimately led Uber from deep losses to a profitable business. We also get into: the immigrant childhood that trained him to adapt faster why betting on people, not models, became the most important lesson of his career the early failures at Expedia that hardened his decision making and leadership style how he rebuilt culture at Uber while operating under intense public scrutiny the long term vision of turning Uber from a rides company into a real time logistics network 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. Dara Khosrowshahi- https://x.com/dkhos 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.

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• 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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