Keith Rabois

Keith Rabois (born March 17, 1969) is an American technology executive, investor, and one of the most prominent members of the PayPal Mafia. Born and raised in Edison, New Jersey, Rabois earned his B.A. in Political Science from Stanford University in 1991, where he became acquainted with Peter Thiel through The Stanford Review. He went on to earn his J.D. from Harvard Law School in 1994 and briefly clerked at a Circuit Court before pivoting away from law and into the technology industry.

Rabois joined PayPal in 2000 as EVP of Business Affairs, Public Affairs, and Policy, playing a key role in the company's growth through its 2002 acquisition by eBay. He subsequently held executive positions at LinkedIn (VP of Business and Corporate Development, 2005-2007), where he expanded revenue streams and launched new products; at Slide (Head of Corporate Development, 2007-2010), the Max Levchin-led social gaming startup acquired by Google for $182 million; and at Square (COO, 2010-2013), where he helped scale the mobile payments company. Since 2000, he has been instrumental in driving five startups from early stages to successful IPOs.

In venture capital, Rabois first joined Khosla Ventures in 2013, where he led first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. He departed for Founders Fund in 2019 as a General Partner under Peter Thiel, then returned to Khosla Ventures in January 2024 as one of five Managing Directors. In 2021, he co-founded OpenStore, a Miami-based e-commerce aggregator that acquires Shopify brands, though the company has since significantly restructured. In September 2025, Rabois returned to Opendoor as Chairman of the Board alongside new CEO Kaz Nejatian, publicly calling for an 85% workforce reduction to restructure the company's cost base.

Rabois is known for a founder-first, conviction-driven investment approach. Rather than adhering to a rigid thesis, he prioritizes backing founders who teach him how the world is changing and what is possible. He evaluates opportunities by asking two core questions: "What is anomalous about this idea or company?" and "What 'secret' is the company predicated on?" -- defining a company secret as a belief system about the world that the rest of the market does not yet appreciate.

He focuses obsessively on identifying top 1% talent and deliberately backs contrarian ideas that others dismiss, making concentrated bets when his conviction is strong rather than spreading investments widely. His focus areas span consumer Internet, financial services, enterprise software, proptech, digital health, and education, with a preference for Bay Area startups at very early stages with technical founders. Rabois has stated that financial success is not his primary motivator; instead, he seeks to be a meaningful influence and help in the success of the entrepreneurs he backs.