HD in HD

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.

“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/

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

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

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

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

How do you go from pitching Sequoia to ringing the bell on a US IPO? Sebastian Siemiatkowski, co-founder and CEO of Klarna was raised in a home where ambition met accountability. Even as Klarna thrived in Sweden, his parents reminded him: “That’s fantastic. When are you going to get your degree?” That grounding, paired with Sebastian’s own ambition to measure up to companies like Google and Facebook, pushed Klarna beyond local success to a global stage. In this episode, we also get into: • how sci-fi books inspired him to see entrepreneurship as an adventure • how Klarna brought Sequoia on board • how Klarna got ahead of Afterpay in the U.S market • navigating co-founder tensions and pivoting leadership • turning Sweden’s strict bill collection into Klarna’s advantage 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. Sebastian Siemiatkowski- https://x.com/klarnaseb 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/ Chapters: 00:00 Intro 05:03 Background and Immigration 12:59 University Life 23:55 Gap Year Adventures 37:57 Finding Multiple Jobs 41:57 The Birth of Klarna 53:42 The First Product 01:15:32 Sequoia's Investment 01:34:50 Entering the US Market 01:49:01 AI and the Future

Before founding Synthesia, Victor Riparbelli grew up in Denmark with parents who struck a balance between ensuring his future security and giving him the freedom to pursue his passions, with his father steering him toward technology. At Stanford, the intense academics and ambitious peers challenged him to question the status quo and honed his approach to creating helpful tools. We also get into: • why complex video games were his first playground for building business • how Mark Cuban became their first investor without meeting them • why the future of communication is video 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. Victor Riparbelli- https://x.com/vriparbelli 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

Before founding Vercel, Guillermo Rauch, was a self-taught teenager in Argentina earning his first dollars online to help his family. From early open-source work to remote freelancing, this episode traces how his drive to figure things out led to solving web performance at scale. We also get into: • how his dad instilled a mindset of pushing tech boundaries • what growing up during Argentina’s economic swings taught him • why he sees Minecraft as a healthy game for his kids • why he believes speed without direction is meaningless 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. Guillermo Rauch- https://www.linkedin.com/in/rauchg/ 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 Intro 02:00 Early Years 04:50 Parenting, First Experiences with Computers 07:40 Screen Time Rules 11:40 Video Games & Developing Programming Skills 15:30 Freelance Coding & Earning in U.S. Dollars 19:40 High School 24:10 Startup Offer 30:30 Silicon Valley & First Acquisition 41:45 Founding Vercel 54:40 AI Wave: v0, Agents & “Token Factories” 01:14:28 Vercel's Success and Client Impact 01:20:58 The Role of AI in Development 01:40:49 Iterating Towards Greatness 01:52:27 Balancing Luck and Skill

With an insatiable appetite for “what’s the new model,” Aaron Levie, Co-founder and CEO of Box, grew up chasing ideas without hesitation: performing magic at birthday parties, building websites, and making short films. In this episode of HD in HD, he shares how a curious mind from early ages became his greatest strength, and how staying slightly uncomfortable kept him ahead of the biggest tech shifts, from SaaS to AI. Today, Box powers content for 100k+ organizations and 68% of the Fortune 500, and is still driven by the same restless energy Aaron had as a teenager, always chasing what’s next. In this episode, we also get into: overcoming critical challenges when scaling storage capacity the move that set Box apart from Dropbox how AI is becoming the next major accelerator for Box 00:00 Intro 00:57 Brex Sponsorship 01:44 Aaron Levy's Early Years 02:24 High School 13:04 College 17:29 The Early Days of Box 23:17 Technological Shifts and Challenges 29:39 Navigating Competition 30:00 Enterprise Differentiation 32:24 Brex Sponsorship 33:12 AI’s Impact on Software and Work 44:51 AI's Role in Enterprise Knowledge Management 48:07 Future of Organizational Design 55:50 AI's Influence on Sales and Marketing 01:03:50 Reflections on Luck, Strategy, and Mistakes 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. Aaron Levie- https://www.linkedin.com/in/boxaaron/ 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/

When Ariel Cohen, co-founder and CEO of Navan, first set out to modernize corporate travel, he wasn’t an industry insider. What he did bring was a relentless focus on fundamentals, constantly asking, “Is it a good business?”, an instinct that arose from his family’s financial struggles, working in cafés, and participating in virtual business competitions in Israel. And that is exactly what led him to build a travel tech giant. In this episode, we also get into: • why building a startup while raising kids gave Ariel motivation to do better. • the supply chain problem in the travel industry. • will AI replace travel agents in the near future? • how Navan’s chatbot helps reduce customers’ travel expenses. 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, click here. Connect with us here: Ariel Cohen Brex Henrique Dubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/

Before co-founding StoneCo, a $3.67B fintech giant, André Street was already thinking like a founder at the age of 14, skipping school not to rebel, but to build. His teacher was life itself, learning discipline from Jiu-Jitsu, gaining “environment intelligence” from being robbed on Rio’s streets, and maturity from an import-export class with 50 year olds. In this episode he joins Henrique Dubugras to unpack: - why he never wanted to be CEO - the prediction he made five years ahead that made StoneCo Brazil’s first independent credit card acquirer - why prioritizing customers early on became the foundation of StoneCo’s business model - the hiring mantra that built one of fintech’s tightest cultures 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 here: 1. StoneCo- https://x.com/SejaStone 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

Howie Liu built Airtable into one of the most powerful no-code platforms in the world—used by over 450,000 companies and backed by everyone from Benchmark to Thrive to YC. In this episode of HD in HD, I was joined by the founder and CEO of Airtable as he reelected on the unexpected turns that shaped his entrepreneurial path—from cold-pitching algo trading models at a college career fair, to building software that powers teams at scale. In our conversation, we get into: why Airtable took 2.5 years to launch—and why it was worth it how a CRM for his personal contacts became his first YC-backed startup what Salesforce taught him about B2B scale (and what it didn’t) how he talked his way into a quant internship that disappeared overnight the $0-to-financial freedom moment that let him finally think big We only scratched the surface on the Airtable chapter, so don’t be surprised if there’s a part two. 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. Connect with us: 1. Howie Liu– https://x.com/howietl 2. Henrique Dubugras– https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com 00:00 Intro 01:20 Introducing Howie and Airtable 02:10 Early life and family 07:33 Early tech 14:13 Building Websites 32:18 Dreaming big 34:07 Middle-Class Entrepreneur Theory 35:55 High school 44:57 College applications 56:40 Duke University 1:05:10 High-paying jobs 1:07:10 Internships and early career 1:09:23 Neural networks and quant trading 1:16:10 New internship 1:22:02 First startup and lessons learned 1:34:22 The birth of Airtable 1:38:27 Outro

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

Everyone ignored this problem—until it became an opportunity. Alexander Rinke, co-founder of Celonis, turned a student project into a $13B+ process mining giant from Germany. Born and raised in Berlin, he went on to build a software empire that has saved companies like Pfizer $300M. This episode of HD in HD explores Alex’s path from student founder to CEO—and how he sees AI transforming the way companies run. Alex and I also unpack: • how 1,500 handwritten letters helped him land Siemens • why AI’s next wave hinges on process overhaul • how a $50K project outgrew his McKinsey dreams 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. Connect with us: 1. Alex - https://x.com/alexanderrinke 2. Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/ 00:00:00 Trailer 00:01:20 Introduction 00:02:40 Process Mining 00:03:59 Real-World Applications 00:06:46 Early Life 00:09:48 Education and Early Career 00:24:32 The Birth of Celonis 00:42:36 Initial Funding Challenges 00:49:45 Scaling and Venture Capital 01:01:15 Mentorship and Role Models 01:05:39 The Future of Celonis and AI 01:13:28 Reflections on Success and Upbringing 01:24:24 Closing Thoughts

Old-school banking leans on control and complacency. Revolut charted its own course—flourishing by bending conventions, outrunning oversight, and favoring execution over protocol. Nikolay Storonsky, Revolut’s co-founder and CEO, was forged by a mix of physics-driven upbringing and competitive swimming. This drilled in his mantra: systems can be cracked, and tenacity outshines flair. That drive transformed Revolut from a currency workaround to a global financial juggernaut, clashing with the establishment. In this episode, we dig into: • Why Nik fueled the start with trading earnings despite later raising $2 billion • How Revolut leapfrogged regulators and legacy players • Why breakneck expansion needs discipline when costs soar and margins tighten explore Nikolay's background other fintech innovators 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. Revolut - https://x.com/RevolutApp 2. Brex - https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugras 00:00 Trailer 00:49 Introduction 01:52 Nik's Early Life and Education 11:50 Transition to Finance and Trading 14:19 The Collapse of Lehman Brothers 25:15 Starting Revolut 36:28 YC Combinator and Fundraising Challenges 41:24 Product Development and Market Fit 44:23 Company Culture and Hiring Philosophy 47:01 Management Style and Systems 59:52 Expansion and Systematizing Processes 01:06:30 Reflections on Success and Challenges 01:09:00 Closing Thoughts This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/

Justin Mateen set out to make dating simple—no lengthy profiles, no uncertainty—just a "yes" or "no" swipe. Today, Tinder’s user base has expanded to 75 million monthly active users. Justin Mateen has continued building on his success by investing early in promising startups such as Brex, Curative Health, Deel, Home Chef, Kalshi, Speak, Whop, and many others, becoming a billionaire along the way. In 2020 he launched JAM Fund, one of the largest Solo VC firms in the world, which has raised approximately $500 million, with $330 million dedicated to its second fund. Business Insider listed Justin Mateen as the number 1 ranked investor in the “Top 100 list of US seed investors” in both 2020 and 2021, with Forbes including Mateen on their list of the decade's top 10 tech entrepreneurs. In this episode, he and I sat down to discuss Tinder’s highs, struggles, and the lessons learned along the way. We also unpack: • the evolution of the 'swipe left/right' phenomenon • whether Facebook played to his subconscious while building Tinder, and why • putting all your eggs in one basket → asymmetric returns Justin’s investing firm, Jam Fund, raised about $300 million from investors for its second fund last year. 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 here:  1. Justin Mateen- https://x.com/Justin_Mateen 2. Brex- https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugras (00:00:00) Intro (00:01:37) Inquisitive childhood (00:05:07) Learning on both fronts (00:10:08) Bullied and trading stocks (00:12:36) Relationship with money (00:15:26) USC and the freshman experience (00:20:47) Lover boy (00:23:47) Financial stability and freedom (00:27:41) From riches to rags (00:31:20) Some things are best lived in your... (00:35:22) Brex (00:36:09) Pre-Tinder (00:40:44) Taylor Swift's website (00:43:43) Ask Me Out (00:50:04) Building trust (00:53:07) The numbers skyrocketed (00:58:20) Existential risk (01:01:04) 13 and a half Staple Centers (01:05:30) Marketing for the first million users (01:15:30) Becoming profitable (01:21:04) Interesting stats (01:23:01) Through a bad breakup (01:34:12) Post-Tinder, Peter Thiel, investing (01:40:26) Short-term options (01:44:48) Never say never (01:48:44) Outro

Bill McDermott bought his first business when he was in high school, and he never looked back. Now, he sits down with Henrique to talk about his early days as a teenage entrepreneur, coming home from his first job interview with his employee badge in his pocket, and what it takes to be the type of leader people still talk about decades later. This episode is brought to you by Brex—a brand I'm proud to have co-founded and one thats shaped by the same journey many of you are on. Brex has everything startups and fast growing companies need to make every dollar count, from modern corporate cards, banking, and treasury to accounting automation, travel, and expenses. Over 25,000 companies, including DoorDash, Scale AI, and Anthropic spend smarter on Brex. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD

An early adopter of the Arpanet, Marcos Galperin went from Buenos Aires to Penn to establishing one of Latin America’s most successful companies, Mercado Libre. Marcos sits down for a candid conversation with Henrique where the two discuss the unique problems of building a South American company, the pivot away from the eBay model of online auctions and Marcos’s run as a champion rugby player. This episode is brought to you by Brex—a brand I'm proud to have co-founded and one thats shaped by the same journey many of you are on. Brex has everything startups and fast growing companies need to make every dollar count, from modern corporate cards, banking, and treasury to accounting automation, travel, and expenses. Over 25,000 companies, including DoorDash, Scale AI, and Anthropic spend smarter on Brex. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD

Beginning in a small town in North Carolina, Zach Perret would eventually go on to form one of the most consequential fintech companies in all of Silicon Valley. Now, the Co-Founder and CEO of Plaid sits down with Henrique Dubugras to talk about being shaped ideologically by Occupy Wall Street, selling and then un-selling to Visa, and how a lead investor once pulled out of a round at the last minute, leading to Plaid being saved by three guys named "Justin".