#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? 🎙️More Episodes🎙️ YouTube: https://bit.ly/3QDLQFt Apple: https://apple.co/478Be6M Spotify: https://spoti.fi/3sfiFiE