Keith Rabois

Stanford

Keith Rabois was an undergraduate at Stanford University, where he edited and wrote for The Stanford Review and was president of the College Republicans. He graduated in 1991 and entered the Stanford Law School that autumn.¹ By his own count he had written 31 columns by early 1992.² The Review had printed several of his articles criticizing Dennis Matthies, the resident fellow of Otero, a freshman dormitory.³ His age is given as 51 in a registration statement filed on November 18, 2020 and as 57 in a proxy statement filed on April 28, 2026.⁴⁵

The Otero incident, January 1992

On the night of Sunday, January 19, 1992, Rabois and two other students passed through Otero on their way to a party, according to Rabois. The head advising associate of the dormitory told The Stanford Daily that he heard one voice screaming "Faggot! Hope you die of AIDS!" and "Can't wait 'til you die, faggot!" toward the resident fellow's cottage. Rabois confirmed the remarks "in substantive content," said they were "mostly about faggots being bad in general," and said that one of his own remarks that night was "See if you can kick me out of housing." He told the paper that Matthies "gets away with intimidating an entire dorm of 80 freshmen every year." Matthies said he assumed the comments were about him but that they were not spoken to him.³

Dean of Students Michael Jackson announced that the students would not be charged under the Fundamental Standard. Jackson's ground was that the 1990 interpretation of the standard reached only face-to-face insults; Law Professor Thomas Grey, who wrote the interpretation, said that yelling at a door could qualify but that the interpretation protected only students, and Matthies was a staff member.¹³ Judicial Affairs Officer Sally Cole said officials had instead chosen to make the case public, so that "the pressure of public disapproval" would fall on the participants.¹ Jackson had sent the Daily a letter, delivered on January 31, that condemned the remarks without naming the students; he said he had not told any of them he would release it.⁶⁷ On February 5 the Daily corrected its earlier reports: one of the other two students had made no remarks, another participant said he "never opened his mouth," and Matthies had not been home at the time. Jackson said the university's investigation had failed to determine exactly who said what.⁶ Residence Dean Angela Rickford said Rabois had told her the week before that he knew "exactly what's permitted at this school" and declined to meet with her or anyone in the administration.⁷

In an unpublished letter to the Daily, Rabois wrote: "I don't necessarily hate homosexuals, but do believe in Jack Kemp's suggestion that they may not be the best teachers of young children in public schools and recognize that the spread of AIDS has a direct causal link back to their activity."⁷ In a column published on February 7 he wrote that the remarks "were about Dennis Matthies, they were NOT directed at him. There was absolutely no reason to believe he was home," that the intention had been "for the speech to be outrageous enough to provoke a thought of 'Wow, if he can say that, I guess I can say a little more than I thought,'" and that when a residence dean called a week later he saw "an interesting opportunity to demonstrate the ridiculousness of the Grey Standard." He wrote: "I figured it would look really bad if they tried to do it to a student who had constantly been a thorn in their side," and "I hate Democrats, not homosexuals; they're the ones that have hurt the country."²

Law students posted fliers bearing his crossed-out photograph and the words "Homophobia is Ugly." More than 400 students, deans, staff and faculty of the law school signed a petition dissociating the school from the remarks, which ran as a half-page advertisement in the Daily; Dean Paul Brest called it "just the appropriate way for the institution to respond." Several students sent the Daily's reports to a Newport Beach law firm at which Rabois was a finalist for a position and said they planned to write to every law firm in California. More than 100 people and reporters from at least three newspapers attended an advertised address by Rabois on "Free Speech, Hate Speech" at which he did not appear.⁶⁸ On February 19 he and Matthies took calls on the premiere of "Talk Back" on KZSU. Rabois cited a letter in the Daily urging readers to write to the California bar to keep him out and said that the letters to potential employers "were not just speech." Asked whether he stood by the remarks, he said: "No, I didn't mean it that way. I don't hate anyone. It was an example."⁹ The Daily still described him as a first-year law student in April 1992, and its year-end review recorded that he had defended the remarks as a test of the Fundamental Standard.¹⁰ His later corporate biographies give a law degree from Harvard University, with honors.⁴⁵

Sullivan & Cromwell and PayPal

Contribution records place Rabois in Washington from 1996 to early 1999. Three gifts in August and September 1998 to the National Republican Senatorial Committee and one to Talent for U.S. Congress, the committee of Representative Jim Talent of Missouri, give his employer as Sullivan & Cromwell; a gift of $1,000 in January 1999 went to Quayle 2000, the presidential committee of Dan Quayle.¹¹ The registration statement of Affirm states that he "began his career in the industry as a senior executive at PayPal and has also practiced as an attorney at Sullivan & Cromwell."⁴

From September 2001 his contributions were filed from Palo Alto with PayPal as employer, several of them describing him as a vice president.¹¹ PayPal's prospectus of February 2002 lists its executive officers and key employees as of December 31, 2001, including Peter Thiel, Max Levchin, David Sacks, Reid Hoffman and the chief financial officer Roelof Botha, and does not include Rabois. Michael Moritz of Sequoia Capital sat on the audit committee with Elon Musk and Shailesh Mehta.¹² Connie Loizos of TechCrunch wrote in 2019 that Rabois had been executive vice president of business development, public affairs and policy at PayPal from late 2000 to late 2002, and that he, Thiel, Ken Howery, Sacks and Joe Lonsdale had worked together at the Review.¹³

LinkedIn, Slide and Square

The Affirm filing lists his later positions as vice president of business and corporate development at LinkedIn, executive vice president of strategy and business development at Slide, the company founded by Levchin, and chief operating officer of Square.⁴ A 2004 contribution gives his employer as Epoch Innovations and his occupation as chief operating officer; a 2008 gift to the John McCain joint committee names Slide; and a $2,400 gift in March 2010 went to Quayle for Congress, the committee of Ben Quayle of Arizona.¹¹ Rabois filed a Form 3 as a director of Yelp with an event date of March 1, 2012.¹⁴

Square's Form D of September 2011, for a $100,000,052 Series C sale, lists Jack Dorsey and Jim McKelvey as executive officers and directors, Rabois as an executive officer, and Botha, Vinod Khosla, Larry Summers and Mary Meeker as directors.¹⁵ The Stanford Daily reported in 2013 that Rabois had joined the company in 2010 and overseen its growth from 17 employees to more than 400.¹⁶

Departure from Square

Rabois resigned as Square's chief operating officer in January 2013. The Stanford Daily reported on January 25, 2013 that a Square employee alleged that Rabois had sexually harassed him and that the company had known of it and failed to act; the company did not identify the employee. Rabois denied the allegation. In a blog post he described a "physical relationship" with the man and wrote that he resigned "so my colleagues could continue to do great work without the distraction that a lawsuit would most certainly bring." Square's statement accepting the resignation said he had "exercised poor judgment." No lawsuit had been filed. Rabois told The Wall Street Journal he was "completely confident that all the facts will come out and I will be vindicated."¹⁶ Loizos wrote in 2019 that Square had said at the time it found no evidence to support the claims.¹³

The board he left included Botha of Sequoia and Khosla. In Square's registration statement of November 2015, Khosla Ventures III, LP held 16.9 percent of the shares and entities affiliated with Sequoia held 5.3 percent; Khosla, a director since June 2011, had tendered his resignation effective before the offering, and Botha and Meeker formed the compensation committee.¹⁷

Khosla Ventures and public boards

Rabois joined Khosla Ventures as a managing director in 2013 and left in 2019.⁴ He filed a Form 3 as a director of Xoom Corporation with an event date of February 14, 2013.¹⁸ On January 17, 2014 he resigned from the board of Yelp, where he was an independent director and chair of the nominating and corporate governance committee, without disagreement with the company.¹⁹ On March 25, 2015 he gave notice of his resignation from Xoom's board, effective after its annual meeting of May 28, 2015; he sat on its nominating and corporate governance committee and its compliance committee.¹⁸ Square's 2015 filing lists Botha as a Xoom director as well.¹⁷ Opendoor's 2025 filing states that he sat on the board of Reddit from 2012 to 2019 and lists early personal investments by him in YouTube, Airbnb and Palantir Technologies.²⁰

He joined the board of Affirm in 2013, as the designee of entities affiliated with Khosla Ventures.⁴ OpenDoor Labs Inc. of San Francisco filed a Form D in May 2014 naming Eric Wu as executive officer and director and Rabois as director.²¹ Contribution records for 2013 and 2015 show $10,600 to Ro for Congress, the committee of Ro Khanna, with Khosla Ventures as employer.¹¹

Founders Fund and Miami

Loizos reported on February 20, 2019 that Rabois was joining Founders Fund as a general partner after six years at Khosla.¹³ Opendoor's 2026 proxy statement dates his Founders Fund partnership from March 2019 to January 2024.⁵ Affirm's registration statement of November 2020 records that Rabois, Thiel and Brian Singerman shared voting and investment power over Affirm shares held by The Founders Fund VI and Founders Fund Growth partnerships; Singerman had resigned from the Affirm board on November 15, 2020, and Rabois remained on it, as a member of the audit committee.⁴

Contribution records give his city as Miami Beach from February 2021.¹¹ In August 2022 Miami Labs, Inc., of North Miami Avenue, Miami, filed a Form D listing Rabois and Jack Abraham as executive officers, directors and promoters, with $31,999,996 sold to three investors; Rabois signed as chief executive officer.²² He returned to Khosla Ventures as a managing partner in January 2024 and served on Affirm's board until June 2025.⁵

Political contributions

Contributions attributed to Rabois in Federal Election Commission itemized records, excluding memo entries that record joint-committee allocations, total $141,500 in 2016, $333,100 in 2020, $895,700 in 2021, $957,100 in 2022, $1,508,500 in 2023, about $2.47 million in 2024, $1,022,000 in 2025 and $1,943,000 in 2026 through early April.¹¹

On March 28, 2016 he gave $50,000 to Never Means Never PAC, a super PAC registered on March 4, 2016, whose independent expenditures from March to June 2016, chiefly online advertising bought from Tusk Digital, were reported as opposing Donald Trump.²³ On October 16, 2020 he gave $25,000 to the Democratic Senatorial Campaign Committee.¹¹ On November 12, 2020 he gave $154,100 to the Senate Georgia Battleground Fund; Doug Leone of Sequoia gave $100,900 to the same committee on November 23.¹¹

From 2021 the larger entries run to House Republican joint fundraising committees: $1,369,700 to Take Back the House 2022 in three gifts between March 2021 and February 2022, $693,700 to Protect the House 2024 in March 2023, and $2,000,000 to Grow the Majority between February 2024 and March 2026. Memo entries attached to these gifts record allocations to Kevin McCarthy for Congress and to Majority Committee PAC, the committee of Kevin McCarthy, in March 2021, February 2022 and March 2023, and to Mike Johnson for Louisiana, the committee of Mike Johnson, in February 2024 and March 2025; across all joint committees, the memo entries assign $1,601,700 of his money to the National Republican Congressional Committee.¹¹ He gave $1,000,000 to SFA Fund, Inc., a hybrid committee affiliated with Team Stand for America, in September 2023 and January 2024, after a $16,600 gift to the joint committee Team Stand for America whose memo entries of August 2023 record transfers to Nikki Haley for President, Inc., the committee of Nikki Haley; $100,000 to The Sentinel Action Fund; $500,000 and later $250,000 and $750,000 to the Congressional Leadership Fund; $200,000 to the Scalise Leadership Fund 2024; and $400,000 to NRSC Victory.¹¹ On September 24, 2024 he gave $250,000 to the Trump 47 Committee, with memo allocations to Never Surrender, Inc., the leadership committee of Trump, and on October 24, 2024 $100,000 to the super PAC Right for America. Leone gave $250,000 to the Trump 47 Committee on October 30, 2024 and $2,000,000 to Right for America on June 4, 2024. On February 17, 2026 Rabois gave $443,000 to the Republican National Committee, recorded in four entries that include its headquarters, convention and legal proceedings accounts.¹¹

Opendoor

On September 10, 2025 Opendoor announced that "Co-Founders Keith Rabois and Eric Wu" were returning to its board, with Rabois as chairman, and that "Khosla Ventures and Wu" were investing $40 million in a private placement.²⁴ Its Form 8-K of the next day recorded stock purchase agreements under which Khosla Ventures Opportunity III, LP bought 5,263,158 shares for $35 million and Wu bought 751,879 shares for $5 million. The board grew from six to eight members; Rabois became a Class I director, chairman, and a member of the audit and risk committee and the compensation committee, and the board found him independent. Khosla Ventures Opportunity III accepted standstill and non-disparagement terms running until 90 days after Rabois leaves the board.²⁰ The proxy statement of April 2026 lists him as an independent chairman and audit committee financial expert, and states that he sits on the private boards of Faire and Ramp.⁵

Rabois's Form 3 reported 615,409 Opendoor shares held directly on September 10, 2025. Forms 4 report grants of restricted stock units in lieu of a $92,500 retainer on February 17, 2026 and of 41,667 units on June 11, 2026, after which he held 630,088 and then 671,755 shares directly. The 2026 proxy lists him as beneficial owner of 680,617 shares, including the 615,409 shares and warrants over 61,539 more.⁵²⁵

Marriage to Jacob Helberg

Jacob Helberg, a senior adviser to the chief executive of Palantir Technologies, was appointed to the U.S.-China Economic and Security Review Commission on January 27, 2023 by Hakeem Jeffries, who wrote that "because of the change in Congress" he was appointing Helberg, "of Miami Beach, Florida," on behalf of the Speaker.²⁶ At his nomination hearing before the Senate Foreign Relations Committee on June 10, 2025, Helberg said: "I would like to thank my husband, Keith."²⁷

Helberg's public financial disclosure report, signed on January 24, 2025, lists consulting fees of $840,000 from Palantir, for services as senior adviser to its chief executive, and, as sources of more than $5,000 in compensation described as clients of his firm Outbuild, LLC of Miami, General Catalyst, Hadrian, Regent Aerospace, UBS, Gusto, Founders Fund, 137 Ventures and Caffeinated Capital. The same report lists, among other assets, interests in Sequoia Capital U.S. Venture Fund, Sequoia Capital U.S. Venture Partners XIV and Sequoia Technology Partners XII, valued at $15,001 to $50,000, $100,001 to $250,000 and $50,001 to $100,000, Affirm stock valued at $1,000,001 to $5,000,000, and Opendoor Technologies stock valued at $500,001 to $1,000,000.²⁸

In an ethics agreement dated May 5, 2025, addressed to Richard C. Visek, the State Department's acting legal adviser and designated agency ethics official, Helberg wrote that his spouse was managing director of Khosla Ventures, had earlier been a general partner of Founders Fund, and held equity and carried interests through both firms in funds listed in an attachment, and that he would not participate in matters affecting Khosla Ventures' financial interests. He listed as sectors of heightened conflict risk "artificial intelligence software; space technology; cybersecurity; digital currencies, including platforms for trading; financial technology; renewable energy development; consumer and enterprise technology; digital health, medical technology, diagnostics, and therapeutics; and edge networking," and wrote: "I am prohibited from sharing nonpublic information with my spouse." The retained funds in Attachment B are management and employee entities of Founders Fund V through VIII and Founders Fund Growth and Growth II, and Khosla Ventures associates entities; their underlying holdings listed there include OpenAI, SpaceX, Anduril Industries, Opendoor Labs, Affirm, Ramp and Stripe.²⁹

The same agreement states that "I and my spouse will divest our interests in the entities listed in Attachment A" within 90 days of confirmation. Attachment A includes the three Sequoia funds, Slow Ventures and SV Angel funds, Palantir, Block and Opendoor Technologies among public companies, and private holdings including Hadrian Automation and Regent Craft.²⁹ The Senate confirmed Helberg on October 7, 2025, by a vote of 51 to 47, in an en bloc confirmation of nominations under S. Res. 412.³⁰ The State Department lists him as Under Secretary for Economic Affairs from October 16, 2025.³¹ In a Sequoia filing of February 2024, Sequoia Capital U.S. Venture Partners Fund XIV, L.P. appears as a Cayman Islands partnership whose general partner, SC U.S. Venture XIV Management, L.P., is in turn managed by SC US (TTGP), Ltd.; the filing names Leone and Botha as the directors and stockholders of SC US (TTGP) who exercise voting and investment discretion.³²

Khosla Ventures, January 2026

After a Border Patrol agent shot and killed a protester, an American citizen, in Minneapolis in January 2026, Rabois wrote on X that "no law enforcement has shot an innocent person. illegals are committing violent crimes every day" and that "interfering w a law enforcement operation is not protected by any of those amendments." Khosla Ventures partner Ethan Choi replied: "I want to make it clear that Keith doesn't represent everyone's views here at @khoslaventures, at least not mine." Vinod Khosla wrote: "I agree with @EthanChoi7. Macho ICE vigilantes running amuck empowered by a conscious-less administration." Julie Bort of TechCrunch, who reported the exchange on January 26, 2026, wrote that Khosla did not directly rebuke Rabois and that the firm did not respond to a request for comment.³³