Keith Rabois — Complete Biography, History, and Inventions

Key Points

• Rabois has been involved and invested in some of most profitable tech companies over the past years, such as Clarium Capital, Khosla Ventures, and the Founders Fund, Opendoor, DoorDash, Scribed, and more!
• His big start came from being a key member of the PayPal Mafia.
• Another big role for him came as COO of Square.

Some of the richest, most powerful men in America are members of the PayPal Mafia, founders and employees of PayPal who went on to found, develop, or fund other tech companies. One such member, Rabois, met PayPal’s future co-founder and fellow PayPal Mafia member, Peter Thiel, while they were both attending Stanford. Since then, his career has been tied to Thiel’s and they have worked together extensively. He has also worked with other PayPal Mafia members, including Reid Hoffman, founder of LinkedIn and Max Levchin, founder of Slide.

He is also known for investing in such companies as DoorDash, Affirm, Trade Republic, and Stripe and co-founding Opendoor.

Who Is Keith Rabois?

Keith Rabois is an American businessman and entrepreneur. A member of the so-called PayPal Mafia, Rabois worked at PayPal before moving onto a series of other businesses. This has included Square, LinkedIn, and more. Like many other members of the PayPal Mafia, Rabois’s career is extensively tied to PayPal co-founder Peter Thiel, and the two have worked together extensively. 

Early Life

Rabois was born on March 17, 1969. His birthplace was Edison, New Jersey. Rabois’s mother was an English and History teacher who eventually transitioned to sales. His father is a Certified Public Accountant (CPA).

Rabois attended college at Stanford University, graduating in 1991 with a B.A. in Political Science. While at Stanford, Rabois met Peter Thiel, future co-founder of PayPal.

His time there was not without controversy: Rabois joined other students in allegedly screaming homophobic insults outside of an instructor’s home. Rabois was punished for the incident, which he characterized as a protest and challenge of rules that Stanford had that were viewed by many as prohibiting freedom of speech.

Rabois would earn a J.D. from Harvard University in 1994. After graduating from Harvard, he clerked for the 5th Circuit Appeals Court. He also spent some time as a corporate litigator before turning to the business sector. 

Career

PayPal

Rabois business career really started when he was hired by PayPal in November 2000. Though he would leave the company two years later, the success that Rabois had at PayPal would set the stage for much of Rabois’s business success. 

Rabois served the company as the Executive Vice President of Business Affairs, Public Affairs, and Policy. This was a critical time in PayPal’s history: The company went public in February 2002. In October 2002, the company was purchased by eBay for $1.5 billion. Rabois left shortly afterward. 

LinkedIn

Rabois next major career stop was at LinkedIn, the company that was founded by a fellow PayPal Mafia member, Reid Hoffman. Rabois would work there from January 2005 – May 2007. His role was Vice President of Business and Corporate Development. 

Rabois’ own LinkedIn profile notes that the company’s user base multiplied tenfold during his time with the network. He lists his accomplishments as having created new corporate advertising streams, LinkedIn Answers, and public profiles. 

Slide

In May 2007, Rabois served as the Executive Vice President for Business and Corporate Development of Slide. Slide was founded by fellow PayPal Mafia member Max Levchin. Slide was a social gaming company. During his time there, Rabois managed the company’s relationships with other social media giants of the time, including Facebook and MySpace. He also ran a variety of corporate departments, including development, strategy, and communications.

Rabois left the company when it was sold to Google in August 2010. The company was sold for $182 million, not including money spent on retention bonuses. 

Square

Rabois’s next stop was Square, the payment processing company, where he served as the company’s Chief Operating Officer. He served in that role from August 2010 – February 2013.

Rabois’ time at Square was cut short by the threat of a sexual harassment lawsuit. According to published reports, a boyfriend of Rabois threatened to sue him for sexual harassment. Rabois admitted that he encouraged the individual to apply for a job at Square, but said that he had nothing to do with his hiring. He called the lawsuit a shakedown and said he was investigating legal and criminal options.

Khosla Ventures

Khosla Ventures marked Rabois’s first formal entry into venture capital, although he had made investments and guided others on the subject in the past. He made numerous successful investments during his time at the company. Rabois stayed there for six years, making his time at Khosla the longest position he had held in his working career.

Founders Fund

Rabois joined the Founders Fund in 2019. His role at the Founders Fund was that of a general partner. The move reunited Rabois with Peter Thiel, co-founder of PayPal, and former member of the PayPal Mafia. 

As part of his role at the Founders Fund, has made it clear that it plans on acquiring similarly situated companies and expanding its business footprint. In November 2021, Rabois announced that he had raised $75 million to purchase Shopify businesses. These Shopify purchases would allow OpenStore, a Rabois-backed business, to purchase merchants that used the Shopify platform. 

What Is Keith Rabois Known For?

PayPal Mafia

Rabois is one of the more successful American businessmen of the past two decades, and like many others, he owes that success to his membership in the so-called PayPal Mafia. This is the group of men that worked at PayPal from its founding to its eventual sale to eBay. Many have gone on to become wildly successful businessmen, and Rabois is one such example.

Furthermore, the relationships that Rabois built during this time proved critical to his future business success. He would repeatedly return to the relationships he built during this time, working with Peter Thiel and Reid Hoffman, among others. 

Startup Success

Rabois’s time with a variety of corporations and investments that he led during his time at Clarium Capital, Khosla Ventures, and the Founders Fund proved highly profitable. His investments included Opendoor, DoorDash, Scribed, and more. 

Rabois parlayed his business expertise into time with other businesses. He served on the boards of many other companies, including Yelp and Xoom. He was also involved in the founding of other businesses, including Opendoor and the Alliance of American football. 

Keith Rabois: Marriage, Divorce, Children, Personal Life

Net Worth

Rabois has a very high net worth, totaling at least $1 billion. He has been involved in a variety of highly successful business launches and IPOs. 

Marriage

Rabois married his husband, Jacob Helberg, in 2018. 

Children

Rabois and Helberg have no children.

Keith Rabois: Awards and Achievements

Keither Rabois has not won any awards that have been noted in his biography or other official sources. 

Keith Rabois: Published Works and Books

Keith Rabois has not published any books.

Keith Rabois: Quotes

“Formula for startup success: Find large highly fragmented industry w low NPS; vertically integrate a solution to simplify value product.” – Tweet from Rabois, 6/2/2017