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

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Sep 19, 2025

Keith Rabois, co-founder of Opendoor and a key figure in the PayPal Mafia, shares invaluable insights on talent scouting and startup culture. He emphasizes that every successful startup resembles a 'cult' driven by exceptional effort. Rabois introduces his 'barrels and ammunition' metaphor for team scaling, while discussing how he identifies extraordinary talent. He reflects on the importance of simplifying complex challenges and offers advice on stress and performance. Plus, he hints at a potential book that promises to be both actionable and broadly appealing.

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INSIGHT

Be The Only One Who Does It

Find and double down on your comparative advantage in life.
Aim to be the only person who does what you do, not just the best at it.

ADVICE

Invest In People With World-Changing Potential

Scout people who have a non-zero chance of changing an industry or the world.
Invest time or capital in those rare candidates and mentor them personally when possible.

ANECDOTE

Hiring From A Quora Post

Keith found Ian Wong from a Quora post and offered him a job without interviews.
Ian started on Monday, later became OpenDoor co-founder and long-term CTO.

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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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