#45 - Keith Rabois

Keith Rabois is a General Partner at Founders Fund and the CEO of OpenStore, which acquires small direct-to-consumer businesses. Keith co-founded Opendoor and led the first institutional investments in DoorDash and Affirm. He has early stakes in YouTube, Palantir, Lyft, Airbnb, Eventbrite, and Wish, and also led investments in Faire, Ramp, Trade Republic, and Stripe. He’s regarded as one of the greatest early stage investors.

Keith began his career in the industry as a senior executive at PayPal and subsequently served in influential roles at LinkedIn and as chief operating officer of Square. As a board member, Keith guided Yelp and Xoom from inception to IPO, and served on the board of Reddit from 2012-2018.

0:00 - Intro
2:35 - Bomb-Building and the PayPal Mafia
5:10 - Spotting Talent
11:32 - Where Keith is 1000:1
16:14 - PayPal, Regulation, and Law
22:00 - Regulatory Arbitrage
25:03 - AI
27:46 - Keith’s 5 Bosses
31:04 - How to Operate
34:16 - OpenStore
39:33 - Founding vs Investing
42:48 - Requests for Startups
47:39 - Early-Stage Investing
53:46 - Companies as Cults
56:42 - The Future of Venture
1:00:56 - Not Stretching, Engineering Serendipity, and How to Ask Better Questions
1:06:40 - On Keith
1:08:45 - Time Allocation, Self-Grading, Values, Reading and Legacy
1:16:11 - What Should More People be Thinking About?

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