EP 62: Keith Rabois (Partner, Founders Fund) Lessons from Peter Thiel & Reid Hoffman, and Why He'd Never Invest in a Remote-First Company

Keith Rabois is a prominent Silicon Valley investor and entrepreneur. He is currently the CEO and founder of OpenStore, and a partner at Founders Fund, a venture capital firm co-founded by Peter Thiel. Prior to this, he served as the COO at Square, a mobile payments company founded by Jack Dorsey, and was also part of the so-called "PayPal Mafia," a group of individuals who co-founded PayPal or worked there in its early days and went on to become successful entrepreneurs and investors. Throughout his career, he has been involved in the founding and growth of many successful technology companies, including Yelp, LinkedIn, and YouTube. In Keith's second appearance on the podcast, he discusses topics such as his dislike for OKRs, his aversion to investing in remote-first companies, and his experiences working with Peter Thiel, Reid Hoffman, and Jack Dorsey.(0:00) Intro(1:14) Welcome back, Keith(5:35) Hating OKRs(10:03) On making decisions(14:09) Not believing in remote work(17:33) Social Issues in the Workplace(19:00) What is the role of a VC?(22:08) Thinking about what can go right(29:35) The "why you" in a potential investment(34:28) Fitting the founder to the story(37:59) The most successful founders are trending older(43:21) The firm brand at Founders Fund(47:57) Lessons learned from Keith's only five bosses in his career(55:48) Thoughts on AI(59:36) Artificial Intelligence in China(1:03:23) What is your most contrarian view today?(1:06:56) On Elon & using Twitter Show Notes:https://twitter.com/raboishttps://www.youtube.com/watch?v=6fQHLK1aIBshttps://delian.io/lessons-3 Mixed and edited: Justin HrabovskyProduced: Rashad AssirExecutive Producer: Josh MachizMusic: Griff Lawson 🎙 Listen to the showApple Podcasts: https://podcasts.apple.com/us/podcast/three-cartoon-avatars/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg