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Keith Rabois, Opendoor ($OPEN) co-founder & newly appointed Board Chair, Managing Director at Khosla Ventures, & a core member of the PayPal Mafia, joins Sourcery for a masterclass on talent, culture, and contrarian thinking. “You don't want to be the best in the world at what you do. You want to be the only one who does what you do.” Paraphrasing Jerry Garcia, The Grateful Dead He shares how he scouts extraordinary individuals, why every successful startup begins as a cult, and the frameworks he’s developed to simplify complex problems into actionable advice. From the Barrels & Ammunition metaphor to building Olympian-level work cultures, Keith reflects on lessons from PayPal, Square, Opendoor, and Khosla. We also dive into his takes on stress, sleep, and performance, his potential book, and why he believes venture capital is the best job for the intellectually curious. Book Recommendations: • Upside of Stress • High Output Management • The Score Takes Care of Itself 1. Keith Rabois: https://x.com/rabois 2. Molly O’Shea: https://x.com/MollySOShea 3. Sourcery: https://x.com/sourceryvc Brought to you by: • Brex—The modern finance platform, combining the world’s smartest corporate card with integrated expense management, banking, bill pay, & travel. As a Sourcery Listener you get: 75,000 points after spending $3,000 on Brex card(s), white-glove onboarding, $5,000 in AWS credits, $2,500 in OpenAI credits, & access to $180k+ in SaaS discounts. On top of $500 toward Brex travel, $300 in cashback, plus exclusive perks (like billboards..) visit → https://brex.com/sourcery • Turing—Turing delivers top-tier talent, data, and tools to help AI labs improve model performance—and enables enterprises to turn those models into powerful, production-ready systems. Visit: https://turing.com/sourcery • Kalshi—The largest prediction market and the only legal platform in the US where people can trade directly on the outcomes of future events: https://kalshi.com/sourcery Follow Sourcery for the latest updates! https://www.sourcery.vc/ (00:00) Keith Rabois (01:22) Mentoring young talent (04:07) Spotting outliers: from Quora posts to Square & Opendoor (06:38) Two formulas for talent: rare excellence or rare combinations (09:00) Lessons from the PayPal Mafia & finding your comparative advantage (09:48) ‘Don’t be the best, be the only one’ (10:29) Frameworks & simplifying complexity for founders (12:16) Barrels & Ammunition metaphor for scaling teams (13:08) Keith’s book: Dangerous Minds (16:34) Olympian work ethic & why 996 is “lazy” (19:13) Culture after COVID & why heroic effort matters early (24:15) Contrarian takes: stress, sleep, Diet Coke, ketchup (29:25) Keith’s energy hacks: Barry’s, cold plunges, red light therapy (32:46) Why venture capital is the best job for the intellectually curious (35:30) Favorite books: Upside of Stress, High Output Management, The Score Takes Care of Itself