Keith Rabois
Born 1969 · Age 56
American technology executive, operator and venture investor; early-stage executive at PayPal, LinkedIn, Slide, Square; investor and founder (Opendoor, OpenStore); member of the PayPal Mafia; managing director at Khosla Ventures and former general partner at Founders Fund.
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Life & Career Timeline
Graduated J.P. Stevens High School (approx.)
Completed secondary education in Edison, NJ (attended J.P. Stevens High School).
Contributor to The Stanford Review and campus free-speech incident
While at Stanford Rabois contributed to The Stanford Review and was later reprimanded as part of a student free-speech incident cited in campus controversies.
Graduated Stanford University (B.A., Political Science)
Received B.A. in political science from Stanford; Phi Beta Kappa and honors.
Graduated Harvard Law School (J.D.)
Received Juris Doctor from Harvard Law School; participated in moot court activities and won awards.
Clerked for U.S. Court of Appeals, Fifth Circuit
Served as a law clerk on the Fifth Circuit (one year), working under Judge Edith H. Jones.
Joined Sullivan & Cromwell as associate
Worked at international law firm Sullivan & Cromwell for nearly four years as an associate.
Policy Director / Adviser for Dan Quayle presidential campaign
Served as an adviser / policy director to Quayle 2000 effort (short-term political role).
Director & VP at Voter.com
Served as director and vice president focusing on business development at Voter.com in early 2000.
Joined PayPal as Executive Vice President
Became Executive Vice President, Business Development, Public Affairs and Policy at PayPal.
PayPal IPO (employee during IPO)
PayPal completed its IPO while Rabois was an executive at the company.
eBay acquisition of PayPal
eBay acquired PayPal (reported ~$1.5 billion); Rabois was a PayPal executive during acquisition.
Entrepreneur-in-residence at Clarium Capital
Served as entrepreneur-in-residence at Peter Thiel's hedge/venture firm Clarium Capital.
CEO of Epoch Innovations
Served as CEO of Epoch Innovations (approx. one year).
Joined LinkedIn as VP, Business and Corporate Development
Served at LinkedIn from Jan 2005 to May 2007, focusing on business & corporate development during major growth.
Joined Slide as Executive VP (Business & Corporate Development)
Moved to Slide (Max Levchin's company) to lead strategy, business development and partnerships (Facebook, MySpace etc.).
Joined Square as Chief Operating Officer (COO)
Became COO at Square (electronic payments company) after several earlier ventures.
Google acquires Slide (~$182M)
Slide was acquired by Google for approximately $182 million; Rabois left Slide around acquisition.
Square named among Fast Company's most innovative companies (during his tenure)
During Rabois' time at Square the company received high rankings from Fast Company for innovation.
Named Quora Top Writer (2013)
Recognized as a 'Top Writer' on Quora for contributions to the platform.
Resigned from Square amid sexual-harassment allegations
Left role as COO at Square after internal controversy and threatened lawsuit over a relationship with an employee; Rabois disputed claims.
Joined Khosla Ventures as managing director
Joined venture firm Khosla Ventures (March 2013) and began investing and advising startups.
Listed as major contributor to FWD.us
Named on the supporters list of FWD.us, a Silicon Valley political/lobbying group focused on immigration and technology policy.
Investments in many high-profile startups (YouTube, Palantir, Lyft, Airbnb, Eventbrite, Wish, Quora, Yammer, etc.)
Rabois has been involved as an early investor in many prominent tech startups (sources vary on timing and exact stakes).
Invested in Yelp and Xoom pre-IPO and insisted on board seats (reported)
Invested in Yelp and Xoom prior to their IPOs; reportedly insisted on taking board seats for both investments.
Co-founded Opendoor (Opendoor Labs)
Co-founded Opendoor, a marketplace for buying and selling homes, launching an online instant-offer model.
Opendoor raised $9.95M (early round)
Opendoor announced a $9.95M funding round from investors (early institutional capital).
Invested in Relcy (reported $9M round)
Wall Street Journal reported Relcy emerged with $9M; Rabois was reported to be involved in the company and funding.
Neighborhood renovation controversy (Glen Park planning dispute)
Planned major remodel of Glen Park home included a penthouse and basketball court; neighbors objected and planning application attracted press.
Scribd $22M round; joined board as observer
After Khosla led a $22M investment, Rabois joined Scribd's board as an observer.
Purchased Glen Park San Francisco house
Purchased a home in Glen Park; planned extensive renovations including penthouse level and basketball court, which drew neighbor pushback.
Married Jacob Helberg
Married Jacob Helberg in Saint Barthélemy; ceremony officiated by Sam Altman.
Public political stance: preferred Trump over Sanders (Jan 2020 comment) & other political commentary
Publicly stated preference to vote for Donald Trump over Bernie Sanders (Jan 2020) and made other political comments; active donor/hosted events later.
Invested in Alliance of American Football and joined board
Joined Peter Thiel and Peter Chernin as investors in the new Alliance of American Football and sat on its board of directors.
Publicly named Pete Buttigieg as top Democratic choice (politics)
Stated Pete Buttigieg was his top choice for the Democratic ticket (2019 commentary).
Public profile as member of 'PayPal Mafia' and high-profile VC operator
Widely recognized in press as a member of the PayPal Mafia and a leading operator-turned-investor in Silicon Valley.
Left Khosla Ventures and joined Founders Fund as General Partner
Departed Khosla Ventures and joined Peter Thiel's Founders Fund as a general partner (publicized Feb 2019).
Invested / involved in theorg.com funding (~$8.5M reported)
The Org collected funding (reported $8.5M); Rabois' Founders Fund was an investor and he has been involved as an investor/advisor.
Moved from California to Miami, Florida
Reported move from San Francisco to Miami (part of broader tech migration to Miami).
Co-founded OpenStore (retail aggregator for Shopify sellers)
Co-founded Miami-based OpenStore (retail-holding startup that acquires Shopify brands).
Named on Forbes / Midas List recognitions
Recognized by Forbes (Midas List inclusion reported in various sources for top investors).
OpenStore raised $75M and reached ~$750M valuation (reported)
OpenStore raised $75 million and was reported to have a $750 million valuation (reported by Forbes/coverage in 2022).
Public net worth estimates reported (~$1B in some sources)
Various profile pieces and aggregation sites have estimated Rabois' net worth in the hundreds of millions to roughly $1 billion range (figures vary by source).
Praised Florida's Parental Rights in Education Act
Publicly praised the Florida law (political commentary reported 2023).
Returned to Khosla Ventures as managing director
Rejoined Khosla Ventures in January 2024 as one of five managing directors after leaving Founders Fund; continues to represent Founders Fund on certain boards.
Left Founders Fund (formal transition) but retained board representations
Departed Founders Fund in January 2024 to rejoin Khosla, while continuing to represent Founders Fund on boards such as Ramp, Found and Trade Republic.
Hosted J.D. Vance fundraiser for Donald Trump campaign
Hosted a fundraiser with husband Jacob Helberg for J.D. Vance benefitting the Donald Trump for President campaign (reported Sep 12, 2024).
Published posts on X supporting Israeli military actions during Gaza War (reported)
Published posts on social media (X) disparaging Palestinians and expressing support for Israeli military actions (reported July 11, 2025).
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