Rabois was born on March 17, 1969 and raised in Edison, New Jersey. Rabois 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.

Between January 2005 and May 2007, Rabois worked at LinkedIn, a social network and job aggregator for working professionals, 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.

Between May 2007 and August 2010, Rabois worked for Slide, a company headed by Max Levchin that focused on slideshows and animations in social networks. Levchin, one of the co-founders of PayPal, knew Rabois from their time together at PayPal. Rabois left Slide around the time that the company was sold to Google.

In 2010, Rabois joined Square, a company that provides an electronic payment service, as its Chief Operating Officer (COO). He left Square in January, 2013 due to the threat of a lawsuit over sexual harassment claims by an employee who obtained a job at Square after beginning a relationship with Rabois.

In March 2013, Rabois joined venture capital firm Khosla Ventures. Rabois left in 2019.

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. Rabois was also listed as a Republican delegate from California during the 2016 Republican National Convention. In January 2020, Rabois stated that he would rather vote for Donald Trump than Bernie Sanders. In 2019 Rabois also stated that Buttigieg was his top choice for the democratic ticket.

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

In January 2015, Rabois joined the board of directors of Scribd after Khosla Ventures led a new investment round in the company.

In November 2015, Rabois purchased a house in Glen Park. A planned renovation received pushback from neighbors.

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.

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

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