Episode 45: Keith Rabois - Managing Director at Khosla Ventures

This week on Generating Alpha, I sat down with Keith Rabois, Managing Director at Khosla Ventures and one of the most accomplished operators and investors in Silicon Valley history.

Keith's path was unconventional. After studying political science at Stanford, where he met Peter Thiel and worked on The Stanford Review, he graduated from Harvard Law School, clerked for the U.S. Court of Appeals for the Fifth Circuit, and practiced as a litigator at Sullivan & Cromwell. That legal foundation became the bedrock for an exceptional career at the intersection of building and investing.

Keith started in tech as an executive at PayPal, then moved to LinkedIn as VP of Business and Corporate Development before becoming COO of Square, helping scale the company through its critical growth years. His operating experience is matched by an extraordinary investing track record. At Khosla Ventures, he led the first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. At Founders Fund, he led investments in Ramp, Trade Republic, and Aven, and made early personal investments in YouTube, Airbnb, Palantir, Lyft, and Eventbrite. He has ranked as high as number four on the Forbes Midas list in the U.S. and number eight globally. In 2021, he co-founded OpenStore, and recently returned to Opendoor's board as Chairman.

In our conversation, we explored how Keith thinks about identifying asymmetric opportunities and how he evaluates talent at the earliest stages. We also discussed his framework for being a great seed investor and why the best people frame themselves as not just the best, but the only.

It's a rare look at one of Silicon Valley's most influential builders and a masterclass in execution, leverage, and long-term value creation.

Presented by: rho.co/generatingalpha