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How to Dominate for Decades | Doug Leone, Sequoia Capital

Aug 30, 2026 · 1:22:18

Doug Leone, who led Sequoia Capital for 26 years, tells David Senra he dominates through fear of irrelevance, and at 69 he is again a 'low-level analyst' racing to understand an AI revolution he calls more radical than anything he has seen. His investment tests are whether he would put his kids' money in, whether it is one of 20 lifetime investments, and whether it can return the whole fund — he wants only 100x outliers and says the biggest venture mistake is selling winners early, citing Sequoia's 20% of NVIDIA and 10% of Google. He recounts backing David Vélez before Nubank existed, Fred Luddy's ServiceNow pitch, and seeking founders who are hypercompetitive with a heart of gold. He advises founders to architect boards like products and to avoid 'completely fucking clueless' investors.

Sam Altman on Building OpenAI & Betting on the Impossible

Aug 23, 2026 · 1:18:17

Sam Altman, CEO of OpenAI, tells David Senra that AI capabilities will outpace society's ability to adapt, and that human connection becomes more valuable as AI improves. Altman cites Shopify CEO Tobi Lütke as the most forward-leaning CEO because he builds with AI himself. He explains OpenAI's platform strategy—one interface, one API—which meant killing Sora and Atlas to focus on general intelligence. He credits Y Combinator's iterative philosophy for making OpenAI possible, even though OpenAI broke the playbook by going four and a half years without shipping a product. He also recalls the first day at Greg Brockman's apartment and says he learns more from successes than failures.

Excellence Is the Capacity To Take Pain | Travis Kalanick, Founder of Uber

Aug 16, 2026 · 1:48:55

Travis Kalanick, founder of Uber and now Atoms, tells David Senra why he is drawn to impossibly hard problems. He recounts Uber's China war against Didi, saying he convinced regulators that progress must be in harmony with stability, and explains his fundraising auction process—starting low, running multiple rooms, building demand curves—versus Benchmark's 'war room' against him. Kalanick also describes running Uber with a 'starve next week' intensity after years of no salary at Red Swoosh, and his management philosophy: fewest possible rules, like mandatory pricing calls before launching cities. His current company, Atoms, applies that to specialized robotics for food, mining, and transport, aiming to digitize the physical world one industry at a time.