Keith Rabois

Keith Rabois
Born	17 3, 1969
Birthplace	Edison, New Jersey, U.S.
Occupation	Entrepreneur, investor, lawyer
Known for	PayPal, LinkedIn, Square, Opendoor, Khosla Ventures
Education	Stanford University (BA) Harvard University (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, venture capitalist, and lawyer who has played a notable role in the development of several prominent Silicon Valley companies over the course of three decades. A managing director at Khosla Ventures, Rabois is recognized as a member of the so-called "PayPal Mafia," a group of former PayPal employees and executives who went on to found or lead major technology companies. His career has spanned executive roles at PayPal, LinkedIn, Slide, and Square, and he co-founded Opendoor, the real estate technology company where he returned as chairman of the board in 2025. As a venture capitalist, Rabois has been an early-stage investor in companies including Yelp, Xoom Corporation, YouTube, Palantir Technologies, Lyft, Airbnb, DoorDash, Affirm, Eventbrite, and Quora. He has appeared on the Forbes Midas List, the publication's annual ranking of top technology investors, five times. Beyond his investing and operating career, Rabois has been a vocal commentator on technology industry practices, startup management, and public policy.

Early Life

Keith Rabois was born on March 17, 1969, and grew up in Edison, New Jersey. Little has been publicly documented about his family background or childhood. He later relocated to California to attend Stanford University, a move that would place him at the center of the emerging technology industry in Silicon Valley.

Education

Rabois attended Stanford University, where he earned a Bachelor of Arts degree. During his time at Stanford in the early 1990s, he became involved in campus debates over free speech and civil liberties, which drew media attention. After completing his undergraduate education, Rabois went on to Harvard University, where he earned a Juris Doctor (JD) degree from Harvard Law School. His legal training would inform aspects of his later career in the technology industry, particularly in his understanding of corporate governance and regulatory matters. Stanford Law School has subsequently hosted Rabois as a speaker, inviting him to discuss his career 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 served in a senior capacity during the company's formative years and rapid growth phase, which culminated in its initial public offering and subsequent acquisition by eBay in 2002. Rabois is identified as a member of the "PayPal Mafia," a term coined by journalists to describe the group of former PayPal founders and early employees who went on to achieve significant influence in Silicon Valley through founding, leading, or investing in numerous technology companies. Other members of this group include Peter Thiel, Elon Musk, Reid Hoffman, and David Sacks. The PayPal experience is frequently cited by Rabois and other alumni as foundational to their approach to building companies and evaluating investments.

LinkedIn and Slide

Following PayPal, Rabois took on executive roles at two additional technology companies. He served as Vice President of Business and Corporate Development at LinkedIn, the professional networking platform founded by fellow PayPal alumnus Reid Hoffman. LinkedIn would later go public in 2011 and was acquired by Microsoft in 2016 for $26.2 billion. Rabois also held an executive position at Slide, a social media application company founded by another PayPal alumnus, Max Levchin. Slide developed social applications for platforms such as Facebook and MySpace before being acquired by Google in 2010.

Square

In August 2010, Rabois joined Square, the mobile payments company founded by Jack Dorsey, as Chief Operating Officer (COO). At Square, Rabois oversaw operations during a period of significant growth as the company expanded its mobile payment hardware and software offerings to small businesses. He participated in company strategy discussions and public appearances representing the firm, including at technology conferences.

Rabois departed Square in January 2013. Square subsequently went public in November 2015 and later rebranded as Block, Inc. in 2021.

Venture Capital: Khosla Ventures

After leaving Square, Rabois transitioned into full-time venture capital investing. He joined Khosla Ventures, the venture capital firm founded by Sun Microsystems co-founder Vinod Khosla, as a managing director. In this role, Rabois has led or participated in investments across a range of sectors including financial technology, real estate technology, consumer internet, and enterprise software.

Among his most prominent 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 services company. These investments contributed to Rabois being named to the Forbes Midas List, an annual ranking of top venture capital investors, on five occasions.

In October 2025, Rabois offered public commentary on career paths in venture capital, advising that it was a "bad idea" for new graduates to enter venture capital immediately after finishing school, arguing instead for the value of operational experience at startups.

In January 2026, Rabois made public remarks regarding U.S. Immigration and Customs Enforcement (ICE) that drew significant attention and prompted Vinod Khosla, the firm's founder, to publicly distance himself and Khosla Ventures from the comments. The incident was reported as having created a public rift between senior figures at the firm.

Early-Stage Investing and Board Roles

Prior to and alongside his role at Khosla Ventures, Rabois established a record as an early-stage investor in companies that later went public or achieved significant valuations. He invested in Yelp, the local business review platform, and Xoom Corporation, the international money transfer service, prior to each company's initial public offering. For both investments, Rabois insisted on securing a seat on the board of directors as a condition of his investment. Xoom was later acquired by PayPal Holdings in 2015.

Rabois has also been involved in investments in YouTube (acquired by Google in 2006), Palantir Technologies, Lyft, Airbnb, Eventbrite, Wish.com, and Quora, among other companies. In 2014, he was involved with a startup called HomeRun, which explored technology-driven approaches to real estate. This interest in real estate technology would lead to his involvement in co-founding Opendoor.

Opendoor

Rabois is a co-founder of Opendoor, a real estate technology company that uses an "iBuying" model to make instant offers on homes, facilitating faster residential real estate transactions. Opendoor went public via a special purpose acquisition company (SPAC) merger in December 2020.

In September 2025, Rabois was named chairman of the board of Opendoor. Concurrently, the company hired Kaz Nejatian, a former Shopify executive, in a senior leadership role. Upon his return to the chairman position, Rabois publicly stated that Opendoor had become "bloated" and called for reducing the company's workforce by approximately 85 percent, from around 1,400 employees to roughly 200. The remarks attracted attention across the business and technology press, with coverage focusing on the aggressive nature of the proposed cost-cutting measures.

In February 2026, Rabois was named to the San Francisco Business Times Newsmaker 100 list for his role at Opendoor.

Other Investments and Activities

Rabois was among the investors in the Alliance of American Football (AAF), a professional American football league that launched in 2019. Peter Thiel's Founders Fund was also an investor in the venture. The league suspended operations after eight weeks due to financial difficulties.

Rabois was listed as a supporter of FWD.us, the immigration reform advocacy group co-founded by Mark Zuckerberg and other technology leaders.

Personal Life

Keith Rabois is married to Jacob Helberg. Helberg is a technology policy figure who has been involved in work related to geopolitical and cybersecurity issues. Rabois is openly gay and has been a public figure in the LGBTQ community within Silicon Valley.

Rabois has resided in San Francisco and has been involved in local real estate matters, including a reported project involving a basketball court at a property in the city.

In the 2020 Democratic presidential primary, Rabois was among Silicon Valley figures noted for their political engagement. During the 2019–2020 cycle, he was identified among technology industry donors who supported Pete Buttigieg's presidential campaign. Coverage of Silicon Valley's political dynamics during the 2020 election cycle noted the range of political perspectives among technology leaders, including Rabois. By 2026, media outlets described Rabois as a vocal supporter of President Donald Trump.

Recognition

Rabois has received recognition primarily through his investment track record and his roles at prominent technology companies. He has been named to the Forbes Midas List, which ranks the top venture capital investors globally based on the performance of their portfolio companies, on five separate occasions. His Midas List appearances have been attributed to his early investments in companies such as DoorDash and Affirm, both of which achieved multi-billion-dollar valuations upon going public.

In February 2026, the San Francisco Business Times included Rabois in its Newsmaker 100 list, recognizing him for his role as chairman of Opendoor and his influence in the Bay Area technology ecosystem.

Rabois has been a frequent speaker at technology industry events, including TechCrunch Disrupt, and has been invited to speak at academic institutions including Stanford Law School on topics related to career development, startup strategy, and venture capital.

Legacy

Keith Rabois's career spans the formative period of the modern Silicon Valley technology ecosystem, from the late 1990s dot-com era through the rise of mobile payments, the platform economy, and the growth of venture capital as a dominant force in technology development. His involvement in PayPal, LinkedIn, Square, and Opendoor places him among a small group of individuals who have held senior executive positions at multiple companies that each achieved valuations in excess of one billion dollars.

As a member of the PayPal Mafia, Rabois is part of a network of entrepreneurs and investors whose interconnected careers have shaped major segments of the technology industry. His transition from operating executive to full-time venture capitalist exemplifies a career pattern common among successful Silicon Valley figures, in which operational experience at high-growth companies is leveraged into an investing career.

His investment portfolio, which includes pre-IPO stakes in Yelp, Xoom, DoorDash, Affirm, YouTube, Palantir Technologies, Lyft, and Airbnb, represents involvement in companies that collectively account for hundreds of billions of dollars in market capitalization. Rabois's insistence on obtaining board seats with his investments—as documented in the cases of Yelp and Xoom—reflects an active, governance-focused approach to venture investing.

Rabois's public commentary on topics including startup management, workforce efficiency, and career development in venture capital has contributed to broader discussions within the technology industry. His 2025 remarks about Opendoor's staffing levels, calling for an 85 percent reduction, drew attention to ongoing debates about operational efficiency in technology companies during a period of industry-wide cost-cutting.