# Keith Rabois

Keith Rabois is an American technology executive and investor, managing director at Khosla Ventures and co-founder of Opendoor, known for early roles at PayPal, LinkedIn, and Square.

Keith Rabois (born March 17, 1969) is an American technology executive and investor. He is a managing director at [Khosla Ventures](https://www.wikiprompt.org/wiki/khosla-ventures) and a co-founder of Opendoor. Rabois was an early-stage startup investor and executive at PayPal, LinkedIn, and Square. He invested in Yelp and Xoom Corporation prior to each company's initial public offering (IPO), insisting on board membership in both cases. Rabois is considered a member of the PayPal Mafia and has been involved in investments in YouTube, Palantir Technologies, Lyft, Airbnb, and other companies.

## Early life and education

Rabois was born on March 17, 1969, in Edison, New Jersey. He studied political science at Stanford University, receiving a B.A. in 1991, and earned a J.D. from Harvard Law School in 1994. While at Stanford, he met [Peter Thiel](https://www.wikiprompt.org/wiki/peter-thiel), then editor and co-founder of The Stanford Review, and later contributed to the libertarian newspaper. Rabois was one of several students reprimanded for shouting homophobic slurs outside an instructor's home, including suggesting the instructor "die of AIDS." Rabois stated the incident was designed to challenge Stanford's rules on student speech; Thiel later defended him in his book, *The Diversity Myth*.

## Career

### Postgraduate and early roles

Rabois clerked for the United States Court of Appeals for the Fifth Circuit for a year and worked at Sullivan & Cromwell for nearly four years. In 1999, he was an adviser to Dan Quayle's presidential campaign.

### PayPal, LinkedIn, and Square

From November 2000 to November 2002, Rabois served as Executive Vice President of Business Development, Public Affairs, and Policy at PayPal. Between January 2005 and May 2007, he was vice president for Business and Corporate Development at LinkedIn, founded by [Reid Hoffman](https://www.wikiprompt.org/wiki/reid-hoffman), also a PayPal Mafia member. In 2010, Rabois joined Square, an electronic payment service, as Chief Operating Officer (COO). He left Square in January 2013 due to a threatened lawsuit over sexual harassment accusations by a male employee; Rabois claimed the relationship was consensual. A Square spokesperson stated that "Keith exercised poor judgment that ultimately undermined his ability to remain an effective leader at Square."

### Venture capital

In March 2013, Rabois joined [Khosla Ventures](https://www.wikiprompt.org/wiki/khosla-ventures) as a managing director, leaving in 2019. In January 2015, he joined the board of Scribd as an observer after Khosla led an investment round. In 2019, he moved to [Founders Fund](https://www.wikiprompt.org/wiki/founders-fund) as a general partner. While there, in 2021, he co-founded OpenStore, a Miami-based retail-holding startup acquiring brands in the Shopify ecosystem, which raised $75 million at a $750 million valuation. Rabois left Founders Fund in January 2024 to rejoin Khosla Ventures as one of five managing directors, but continues to represent Founders Fund on the boards of Ramp, Found, Trade Republic, and Pietra.

### Other ventures

In April 2014, Rabois co-founded Opendoor, a home buying and selling marketplace. In March 2018, he invested in the Alliance of American Football alongside Peter Thiel and Peter Chernin, sitting on the league's board of directors.

## Politics

In April 2013, Rabois was listed as a major contributor to the lobbying group FWD.us. In January 2020, he stated he would rather vote for Donald Trump than Bernie Sanders. In 2023, he praised Florida's Parental Rights in Education Act. In September 2024, he hosted JD Vance for a fundraiser supporting Trump's presidential campaign. During the Gaza war, Rabois regularly expressed support for the Israeli government and rejected evidence of Palestinian civilian deaths, asserting the IDF was "the most ethical military in world history." On the day of the killing of Alex Pretti, he claimed that "no law enforcement has shot an innocent person" and that "illegals are committing violent crimes every day." [Vinod Khosla](https://www.wikiprompt.org/wiki/vinod-khosla) and partner Ethan Choi subsequently disavowed his comments about ICE.

## Personal life

In November 2015, Rabois purchased a house in San Francisco's Glen Park neighborhood, planning a renovation with a penthouse, basketball court, lockers, and sauna, but faced pushback from six neighbors. In 2018, he married Jacob Helberg; the ceremony in Saint Barthélemy was officiated by [Sam Altman](https://www.wikiprompt.org/wiki/sam-altman). In November 2020, they moved from California to Miami, Florida. In February 2025, the Wall Street Journal reported they sought to sell their Miami Beach home for $65 million.

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Source: https://www.wikiprompt.org/wiki/keith-rabois
License: CC BY-SA 4.0 (https://creativecommons.org/licenses/by-sa/4.0/)
Last updated: 2026-09-12T22:19:54.836888+00:00