Keith Rabois

Early life and education

Rabois was born on March 17, 1969, and raised in Edison, New Jersey. He studied political science as an undergraduate at Stanford University, receiving his B.A. in 1991 and a J.D. from Harvard Law School in 1994. While at Stanford, he became acquainted with Peter Thiel, then-editor and co-founder of The Stanford Review. Rabois later contributed to the libertarian newspaper. Rabois was one of several students reprimanded for shouting homophobic slurs outside an instructor's home, including the suggestion that the instructor "die of AIDS." Rabois stated that the incident was designed to challenge Stanford's rules on student speech. Thiel later defended Rabois in his book, The Diversity Myth: Multiculturalism and Political Intolerance on Campus.

Career

Postgraduate

He clerked for the United States Court of Appeals for the Fifth Circuit for a year and worked at Sullivan & Cromwell for nearly four years.

Information Technology

PayPal

Rabois was Executive Vice President, Business Development, Public Affairs, and Policy at PayPal from November 2000 to November 2002.

LinkedIn

Between January 2005 and May 2007, Rabois worked at LinkedIn as its vice president for Business and Corporate Development. LinkedIn was founded by Reid Hoffman, also a former employee at PayPal and a member of the PayPal Mafia.

Square

After some unsuccessful ventures, in 2010, Rabois joined Square, a company that provides an electronic payment service, as its Chief Operating Officer (COO).

Sexual harassment charge

Rabois left Square in January 2013 due to the threat of a lawsuit over sexual harassment accusations by a male employee; Rabois claims that the relationship was consensual. A spokesperson from Square said in a statement that "Keith exercised poor judgment that ultimately undermined his ability to remain an effective leader at Square."

Venture capital

Khosla Ventures

In March 2013, Rabois joined venture capital firm Khosla Ventures. Rabois left in 2019. In January 2015, Rabois joined the board of directors of Scribd as an observer after Khosla Ventures led a new investment round in the company. Rabois returned to Khosla Ventures in January 2024 as one of five managing directors.

Founders Fund

In 2019 Rabois left Khosla Ventures and joined Founders Fund as a general partner.

In 2021 while at Founders Fund Rabois co-founded Miami-based OpenStore, a retail-holding startup that acquire brands in the Shopify ecosystem. It raised $75 million at a $750 million valuation.

Rabois left Founders Fund in January 2024 to rejoin Khosla Ventures, but continues to represent it on the boards of Ramp, Found, and Trade Republic. and Pietra.

Other ventures

Opendoor

In April 2014, Rabois co-founded Opendoor, a home buying and selling marketplace.

Alliance of American Football

In March 2018, Rabois invested in the Alliance of American Football, along with Peter Thiel and Peter Chernin. He sat on the league's board of directors.

Politics

In April 2013, a lobbying group called FWD.us was launched, with Rabois listed as one of a major contributor on the group's website. In January 2020, Rabois stated that he would rather vote for Donald Trump than Bernie Sanders. In 2019 Rabois also stated that Pete Buttigieg was his top choice for the Democratic ticket.

In 2023, Rabois praised the Parental Rights in Education Act law in Florida.

On September 12th, 2024, he and his husband, Jacob Helberg, hosted J.D. Vance for a fundraiser benefitting the Donald Trump for President campaign.

During the Gaza War, Rabois published multiple posts on X disparaging Palestinians, indicating his support for Israeli military activity, and rejecting documented evidence of Palestinian civilians killed in Israeli airstrikes. In one post, he called the Israeli military "the most ethical military in world history".

Keith Rabois voiced his support for ICE activity in Minnesota where two people were killed via X / Twitter after a second protestor was shot and killed by ICE while legally monitoring ICE activity in Minneapolis: "no law enforcement has shot an innocent person" and that "illegals are committing violent crimes every day." Khosla Ventures founder Vinod Khosla and partner Ethan Choi subsequently disavoved Rabois' comments about ICE.

Personal life

In November 2015, Rabois purchased a house in the Glen Park neighborhood of San Francisco. He planned a renovation that included a new penthouse level, a basketball court, lockers and a sauna, but received pushback from six of his neighbors.

In 2018, Rabois married Jacob Helberg. The ceremony held in Saint Barthélemy was officiated by Sam Altman.

In November 2020, it was reported that they moved from California to Miami, Florida. In February 2025, the Wall Street Journal reported that Rabois and Helberg were seeking to sell their Miami Beach home for $65 million.

Keith Rabois, a managing director at Khosla Ventures, wrote in a post on X on Saturday, 1/24/2026, that "no law enforcement has shot an innocent person" and that "illegals are committing violent crimes every day."

References

References

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7. (20 February 2020). "The Org collects $8.5 million from Founders Fund and Sequioa to publish organisation charts of companies". Tech.eu.
8. "Keith Rabois: Did you really grow up in Edison".
9. Weigel, Moira. (December 20, 2021). "The Making of Peter Thiel's Networks". The New Republic.
10. (November 18, 2019). "In Keith Rabois' Silicon Valley, Nice Guys Finish Last".
11. "Masters of Their Domain". Mother Jones.
12. (1992-02-12). "Officials condemn homophobic incident, no prosecution planned".
13. (2013-01-26). "Keith Rabois, COO Of Square, Resigns After Relationship With Employee, Harassment Allegations". HuffPost.
14. Packer, George. (November 28, 2011). "No Death, No Taxes".
15. Trotter, J. K.. "The Free Speech Peter Thiel Will Defend: "Faggot! Faggot! Hope You Die of AIDS!"". Gawker.
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24. Ha, Anthony. (2015-01-02). "Scribd Raises $22M For Its Subscription E-Book Service". TechCrunch.
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29. Shah, Saqib. "PayPal Mafia's Keith Rabois has acquired 40 Shopify sellers in the past year through his startup OpenStore. He's not slowing down despite the recent problems in the aggregator space.". Business Insider.
30. Konrad, Alex. "OpenStore Raises $75 Million To Acquire More Shopify Sellers, Reaches $750 Million Valuation In Eight Months". Forbes.
31. (2014-04-03). "Khosla Ventures' Keith Rabois finally launches his real estate startup".
32. (7 July 2014). "Keith Rabois' Homebuying Startup OpenDoor Raises $9.95M From Everyone". TechCrunch.
33. (2014-05-29). "Here's investor Keith Rabois' bold new home-selling startup: OpenDoor". VentureBeat.
34. (20 March 2018). "Peter Thiel's venture firm is backing a new football league to rival the NFL". CNBC.
35. "Our supporters". FWD.us.
36. (2 March 2020). "NY Times:Silicon Valley Leaders' Plea to Democrats: Anyone but Sanders". The New York Times.
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38. Calanacis, Jason. (Feb 22, 2019). "E905 PT2 Keith Rabois PayPal/FoundersFund: censorship, secondary shares, selling, getting into tech". YouTube.
39. Keith Rabois. "Sounds like a wise policy to me.".
40. Theodore Schleifer. (27 August 2024). "JD Vance is keeping up his aggressive fund-raising schedule on behalf of Trump". New York Times.
41. Rabois, Keith. (July 11, 2025). "Keith Rabois denying Palestinian deaths, claiming Israeli military is most ethical military in history".
42. Roya Shahidi. (26 January 2026). ["Billionaire VC founder Vinod Khosla distances himself from pro-ICE remarks by an exec at his firm"](https://www.businessinsider.com/vinod-khosla-criticizes-pro-ice-remarks-minneapolis-exec-keith-rabois-2026-1=Business Insider).
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47. (2017-03-29). "Tech Entrepreneur's San Francisco Remodel Upsetting Neighbors".
48. Schleifer, Theodore. (2019-05-07). "How Pete Buttigieg became the new toast of Silicon Valley's wealthiest donors". Vox.
49. (12 Jan 2019). "Instagram post by Jacob Helberg".
50. Robert Hackett. (17 November 2020). "Silicon Valley loses another tech icon". Fortune.
51. Clarke, Katherine. (2025-02-27). "Exclusive {{!}} Trump Appointee Wants $65 Million for His Bayfront Miami Beach Mansion".
52. Shahidi, Roya. "Billionaire VC founder Vinod Khosla distances himself from pro-ICE remarks by an exec at his firm".