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/rabois

https://www.youtube.com/watch?v=6fQHLK1aIBs

https://delian.io/lessons-3

Mixed and edited: Justin Hrabovsky

Produced: Rashad Assir

Executive Producer: Josh Machiz

Music: Griff Lawson

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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📱 X - https://twitter.com/loganbartshow

🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow

About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.

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