Keith Rabois

Keith Rabois
Rabois in 2011
Keith Rabois
Born	17 3, 1969
Birthplace	Edison, New Jersey, U.S.
Nationality	American
Occupation	Entrepreneur, investor, lawyer
Known for	PayPal, LinkedIn, Square, Opendoor, Yelp, Xoom
Education	Stanford University (BA) Harvard Law School (JD)
Spouse(s)	Jacob Helberg
Awards	Forbes Midas List (five-time honoree)
Website	[http://www.rabois.com/ Official site]

Keith Rabois (born March 17, 1969) is an American technology executive, entrepreneur, and venture capital investor. He is a managing director at Khosla Ventures and is recognized as a member of the so-called "PayPal Mafia," the influential group of former PayPal executives and founders who went on to establish or lead major Silicon Valley companies. Over a career spanning more than three decades, Rabois has held executive roles at PayPal, LinkedIn, Slide, and Square, and co-founded the real estate technology company Opendoor. As an investor, he has been involved in early-stage funding rounds for companies including Yelp, Xoom, YouTube, Palantir Technologies, Lyft, Airbnb, Eventbrite, DoorDash, and Affirm. Rabois has been named to the Forbes Midas List—a ranking of the top technology investors—on five occasions. His career has intertwined operational leadership at high-growth startups with venture investing, making him one of the more prominent figures in the Silicon Valley technology ecosystem.

Early Life

Keith Rabois was born on March 17, 1969, and grew up in Edison, New Jersey. Details regarding his family background and childhood are not extensively documented in public sources.

While a student at Stanford University in the early 1990s, Rabois became the subject of significant media attention and controversy. In 1992, Rabois, then a first-year law student, stood outside the residence of a Stanford instructor and shouted homophobic epithets, an incident that was widely reported at the time. Rabois later stated that the act was intended as a deliberate provocation to test the boundaries of free speech protections, though the episode drew sharp criticism from the Stanford community. The incident would be revisited in later years in media profiles, particularly in the context of Rabois's own identity as a gay man and his subsequent marriage to Jacob Helberg.

Education

Rabois attended Stanford University, where he earned a Bachelor of Arts degree. He subsequently enrolled at Harvard Law School, where he obtained a Juris Doctor (JD) degree. His legal education provided a foundation that he would draw upon throughout his career in technology, where he frequently engaged with issues of corporate governance, intellectual property, and regulatory strategy. Stanford Law School later invited Rabois to speak about his career trajectory spanning law, startups, and venture capital.

Career

PayPal and the PayPal Mafia

Rabois was an early executive at PayPal, the online payments company co-founded by Peter Thiel and Max Levchin, among others. At PayPal, he worked alongside a cohort of individuals who would later become some of the most prominent figures in Silicon Valley, including Thiel, Elon Musk, Reid Hoffman, and David Sacks. This group of former PayPal executives became known informally as the "PayPal Mafia" because of the outsize influence its members exerted on the technology industry in the years following PayPal's acquisition by eBay in 2002.

Rabois's tenure at PayPal established his reputation as an operator capable of managing rapid growth at technology companies. The experience also cemented his relationships with a network of entrepreneurs and investors who would collaborate and co-invest repeatedly in subsequent ventures.

LinkedIn and Slide

Following his time at PayPal, Rabois served as an executive at LinkedIn, the professional networking platform founded by fellow PayPal alumnus Reid Hoffman. He later held a role at Slide, a social entertainment company founded by another PayPal co-founder, Max Levchin. These positions reflected a pattern in Rabois's career of joining companies led by former PayPal colleagues during their early, high-growth stages.

Square

In August 2010, Rabois joined Square, the mobile payments company founded by Jack Dorsey, as chief operating officer (COO). His hiring was reported as a significant addition to the company's executive team, given his track record at PayPal and LinkedIn. At Square, Rabois oversaw business operations as the company scaled its mobile payment products for small businesses and individuals. He spoke publicly on behalf of the company at technology conferences, including the 2011 Mobilize conference.

In January 2013, Rabois resigned from Square. His departure was reported by multiple news outlets.

Venture Capital: Khosla Ventures

Following his departure from Square, Rabois transitioned into a full-time venture capital career. He joined Khosla Ventures, the firm founded by Sun Microsystems co-founder Vinod Khosla, as a managing director. In this role, Rabois led investments in a range of technology companies across sectors including financial technology, logistics, real estate technology, and consumer internet.

Among his most notable investments at Khosla Ventures, Rabois led the firm's early-stage investments in DoorDash, the food delivery platform that went public in December 2020, and Affirm, the buy-now-pay-later financial technology company. These two investments were instrumental in securing Rabois's repeated appearances on the Forbes Midas List, which ranks the most successful venture capital investors globally. As of 2025, Rabois had been named to the Midas List five times.

In addition to DoorDash and Affirm, Rabois has been involved in investments in a wide array of companies. Prior to joining Khosla Ventures full-time, he made early-stage investments in Yelp and the Xoom Corporation, insisting on obtaining a seat on each company's board of directors as a condition of his investment. Both companies subsequently went through initial public offerings. His portfolio has also included investments in YouTube, Palantir Technologies, Lyft, Airbnb, Eventbrite, and Quora, among others.

In October 2025, Rabois offered public advice to aspiring venture capitalists, stating that it was a "bad idea" for new graduates to enter the venture capital industry immediately after finishing school, suggesting instead that they first gain operational experience at startups or established companies.

In January 2026, a public rift emerged between Rabois and Khosla Ventures founder Vinod Khosla after Rabois made comments on social media perceived as supportive of U.S. Immigration and Customs Enforcement (ICE) following a fatal shooting by federal officers in Minneapolis. Khosla publicly distanced himself and the firm from Rabois's remarks, stating that they did not represent the views of Khosla Ventures. The incident attracted widespread media coverage and highlighted tensions within the firm.

Opendoor

Rabois co-founded Opendoor, a real estate technology company that uses algorithmic pricing to make instant offers on residential homes, a model known as "iBuying." The company became one of the most prominent ventures in the proptech sector.

In September 2025, Rabois was named chairman of the board of Opendoor. His return to a leadership position at the company was accompanied by the hiring of former Shopify executive Kaz Nejatian. In public statements at the time, Rabois described the company as "bloated" and called for a dramatic reduction in its workforce. He stated that Opendoor did not need its then-current workforce of approximately 1,400 employees and suggested the company could function effectively with roughly 200 employees—a cut of approximately 85 percent. The remarks generated significant attention in business and technology media.

Rabois was also named to the San Francisco Business Times' "Newsmaker 100" list in recognition of his role at Opendoor and his broader influence on the Bay Area business community.

Other Investments and Activities

Beyond his primary roles, Rabois made an early investment in HomeRun, a company in the home services space, in 2014. He was also listed among the supporters of FWD.us, the immigration reform advocacy group co-founded by Facebook CEO Mark Zuckerberg, which lobbied for comprehensive immigration reform and expanded visas for skilled workers.

Rabois was an investor in the Alliance of American Football, a professional American football league that launched in 2019. The league received backing from Founders Fund, the venture capital firm led by Peter Thiel.

Personal Life

Rabois is openly gay. He is married to Jacob Helberg, a technology executive and government official who has served in roles related to technology policy and national security.

Rabois has resided in the San Francisco Bay Area for much of his career. In 2017, it was reported that he had constructed a private outdoor basketball court at his San Francisco property, a project that drew some local media coverage.

During the 2020 U.S. presidential election cycle, Rabois was among a number of Silicon Valley figures whose political activities attracted media scrutiny. He was not among the technology industry figures who supported Bernie Sanders's presidential campaign, with reporting by The New York Times highlighting divisions within the technology sector over political candidates. During the 2019 Democratic primary cycle, Rabois was among Silicon Valley donors who expressed interest in Pete Buttigieg's presidential campaign. In more recent years, Rabois has been described in media reports as a supporter of former President Donald Trump, with TechCrunch characterizing him as an "unwavering Trump loyalist" in January 2026.

Recognition

Rabois has received recognition within the technology and investment communities for his career as both an operator and an investor. His most prominent accolade is his five-time inclusion on the Forbes Midas List, which ranks the world's leading venture capital investors based on the performance of their portfolio companies. His investments in DoorDash and Affirm were cited as particularly significant contributors to his standing on the list.

He was named to the San Francisco Business Times' "Newsmaker 100" list, a ranking of influential figures in the Bay Area business community, in recognition of his leadership role at Opendoor and his broader investment activities.

Rabois is a frequent speaker at technology industry conferences and events. He spoke at the 2011 TechCrunch Disrupt conference and has participated in panels and presentations at numerous other industry gatherings. Stanford Law School invited him to deliver a talk on careers spanning law, startups, and venture capital, reflecting his status as a notable alumnus of both Stanford and Harvard.

Legacy

Keith Rabois's career exemplifies a pattern common among members of the PayPal Mafia: leveraging early experience at a transformative technology company into a broader career spanning company building and venture investing. His operational roles at PayPal, LinkedIn, and Square gave him direct experience in scaling technology companies, while his investments in firms such as Yelp, Xoom, DoorDash, Affirm, YouTube, and Airbnb placed him at the center of many of the most consequential developments in consumer internet and fintech over the past two decades.

His co-founding of Opendoor represented an attempt to apply technology-driven approaches to the residential real estate market, one of the largest and most traditional sectors of the American economy. As chairman of the company's board, Rabois continued to advocate for operational efficiency and lean organizational structures, as reflected in his September 2025 statements about drastically reducing the company's headcount.

Rabois's career has also been marked by public controversies, from the 1992 incident at Stanford to the 2026 clash with Vinod Khosla over his social media remarks about ICE. These episodes have made him a polarizing figure in Silicon Valley, even as his investment track record has earned him consistent recognition among the technology industry's leading investors.

His advice to aspiring venture capitalists—to gain operational experience before entering the field—reflects a philosophy that has informed his own career, in which hands-on executive roles preceded and informed his investment activities.