Keith Rabois: Lessons from PayPal Mafia, $OPEN, & Investing

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 DeadHe 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 Itself1. Keith Rabois: https://x.com/rabois2. Molly O’Shea: ⁠https://x.com/MollySOShea⁠3. Sourcery: ⁠https://x.com/sourceryvc⁠Brought 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/sourceryFollow Sourcery for the latest updates!https://www.sourcery.vc/