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

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

Update: 2025-09-19
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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


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

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

Sourcery with Molly O'Shea