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Guillermo Rauch, founder of Vercel and a self-taught tech visionary from Argentina, shares his inspiring journey from selling CDs to revolutionizing web applications. He discusses the importance of technical knowledge for CEOs and how his father’s encouragement shaped his hacker mentality. Rauch reflects on the economic lessons from his upbringing and emphasizes cultivating creativity in kids. The conversation also touches on AI's role in democratizing coding, the evolution of web technologies, and how the intersection of luck and skill shaped his innovative path.

Aaron Levie, Co-founder and CEO of Box, shares his journey from a curious kid performing magic to leading a major cloud enterprise. He discusses the challenges of scaling storage and how Box differentiated itself from Dropbox. Levie emphasizes the transformative role of AI in enhancing business models and organizational design. With over 100,000 clients, he highlights the importance of embracing discomfort and curiosity to stay ahead in the tech landscape. His insights into the interplay of luck, strategy, and innovation offer a captivating glimpse into the future of enterprise solutions.

Ariel Cohen, the co-founder and CEO of Navan, shares his inspiring journey in the travel tech industry. He discusses the challenges of scaling Navan globally, including adapting to the COVID-19 pandemic. Ariel reflects on how raising kids fueled his motivation and highlights his chatbot's role in reducing travel costs. He explores the ongoing debate around AI potentially replacing travel agents and the importance of human connections in an increasingly digital world. His insights provide a fresh perspective on entrepreneurship and industry resilience.

André Street, co-founder of the $3.67 billion fintech giant StoneCo, shares his entrepreneurial journey that began at just 14. He reveals why he never wanted to be a CEO and the pivotal early customer focus that shaped his business model. Street discusses the importance of understanding problems before solutions and his hiring mantra that fostered a strong company culture. He also uncovers insights from his transition into new markets like Europe, emphasizing resilience and the critical lessons learned along the way.

Howie Liu, founder and CEO of Airtable, shares his journey from pitching algo trading models at a college fair to building a billion-dollar no-code platform used by over 450,000 companies. He discusses the two-and-a-half-year wait before Airtable’s launch and how it ultimately paid off. Liu reflects on his experiences with Salesforce, his unexpected quant internship, and the pivotal moment that led to his financial freedom. Throughout, he emphasizes the importance of perseverance, creativity, and addressing real-world problems.

Jack Zhang, Co-founder and CEO of Airwallex, journeyed from a small town in China to building a billion-dollar tech story in Australia. He discusses how Airwallex differentiated itself from Stripe in the APAC market and reflects on a costly mistake that almost derailed their first client. Jack shares insights on navigating the 2022 valuation reset without panic, and highlights an overlooked AI opportunity in fintech. With Airwallex hitting $1B in volume before a proper Series A, his story is one of resilience and innovation in the global payments landscape.

Alex Rinke, co-founder and CEO of Celonis, transformed a student project into a $13B software giant while taking on inefficiencies in major corporations like Pfizer. He shares how 1,500 handwritten letters helped secure a deal with Siemens and discusses the pivotal role of process mining in operational efficiency. Rinke highlights the challenges of navigating startup life and scaling innovations, plus the future of AI in business. Tune in for insights on entrepreneurship, personal growth, and the necessity of data transparency!

Nikolay Storonsky, CEO and Co-founder of Revolut, dives into his journey of building a $33B fintech empire. He reveals why ignoring traditional banking norms propelled Revolut’s success. Nik discusses his decision to stop relying on VCs even after raising $2 billion and how the company navigated the complexities of regulatory frameworks. He emphasizes that systems can be hacked and endurance is key, outlining lessons learned from early challenges and the importance of culture and metrics in driving efficiency within a fast-paced startup environment.

Justin Mateen, co-founder of Tinder and investor through Jam Fund, explores the revolutionary impact of swiping on dating. He shares the origin story of Tinder, revealing how simplicity was key to its success. The conversation delves into user behavior differences, especially between men and women, as well as the grassroots marketing strategies that fueled Tinder's growth. Mateen also reflects on the emotional toll of public backlash and his transition from entrepreneur to investor, emphasizing the lessons learned throughout his journey.

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