Keith Rabois

Ramp counts the days since it started, which lets Eric Glyman state precisely how present his investor has been: Keith Rabois has been involved on 98 percent of them.¹ That is not the ordinary relationship between a board member and a company, and it is the clearest evidence of what Rabois actually does for a living.

Rabois is an American technology executive and venture capital investor at Khosla Ventures, previously a senior operating executive at PayPal, LinkedIn, Slide, and Square, and a co-founder of the real estate marketplace Opendoor. Since 2013 he has worked mainly as an investor, first at Khosla Ventures, then at Founders Fund, then back at Khosla Ventures, where he sits on the boards of companies including Ramp, Affirm, DoorDash, and Faire. He is widely known in startup circles for an opinionated, publicly circulated view on hiring.

Background

Rabois was born in 1969 and raised in Edison, New Jersey. He studied political science as an undergraduate at Stanford University, graduating in 1991, and went on to Harvard Law School, receiving his J.D. in 1994. At Stanford he became friendly with Peter Thiel, then an editor and co-founder of the conservative student publication The Stanford Review, a relationship that later brought him into the PayPal orbit. His time at Stanford was also marked by a disciplinary incident in which he was reprimanded, along with other students, for shouting slurs outside an instructor's home. Rabois has said the episode was intended to test the university's speech rules. After law school he clerked for a judge on the U.S. Court of Appeals for the Fifth Circuit, then practiced as a litigator at Sullivan & Cromwell.

Getting started

Rabois left law practice for technology at the end of the 1990s, joining PayPal as executive vice president of business development, public affairs, and policy. PayPal, an online payments company, was staffed with an unusually concentrated group of future founders and investors later known as the "PayPal Mafia," including Thiel, Elon Musk, Reid Hoffman, and Max Levchin. eBay acquired PayPal in 2002. Rabois followed several of these colleagues into subsequent ventures, joining Hoffman's professional networking company LinkedIn as vice president of business and corporate development, then Slide, a social-media startup founded by Levchin. In 2010 he became chief operating officer of Square, the payments and point-of-sale company co-founded by Jack Dorsey and Jim McKelvey, running day-to-day operations during a period of rapid growth. He resigned from Square in 2013 after a subordinate accused him of sexual harassment, an allegation he denied and which was settled. The episode ended his run as a line operating executive and marked his shift toward investing. Later that year, drawing on his relationship with Vinod Khosla from Square's board, he joined Khosla Ventures. In 2014, while at Khosla, he co-founded Opendoor with Eric Wu, Ian Wong, and JD Ross, a company built to buy and resell homes directly from sellers using an algorithmic pricing model.

What he built

At Khosla Ventures, Rabois led the firm's first institutional investments in several companies that became large outcomes, including DoorDash, Affirm, and Faire, and invested early in Stripe. Opendoor itself, the company he co-founded, raised its first venture round in 2014 led by Khosla Ventures, launched its home-buying pilot in Phoenix, and later went public through a 2020 merger with a special-purpose acquisition company, though its stock and business model came under significant pressure during the 2022-2023 downturn in the housing market. In 2019 Rabois left Khosla Ventures to become a general partner at Founders Fund, the venture firm co-founded by Thiel. While there, in 2021, he co-founded OpenStore, a Miami-based company that acquired and operated small e-commerce brands built on Shopify, reportedly raising tens of millions of dollars at a valuation in the hundreds of millions. In January 2024 Rabois left Founders Fund and returned to Khosla Ventures as a managing director, while continuing to represent Founders Fund's interests on several boards, including Ramp, Found, Trade Republic, and Pietra. As an investor, he has been an unusually hands-on board member; the expense-management company Ramp has described him as closely involved in its operations on a near-daily basis since investing.¹

How he operates

Rabois' signature as an operator and investor is a codified philosophy of hiring, delivered publicly as an "art of hiring" talk and reinforced in his advising of portfolio companies. He argues that founders should hire for narrow, extreme strengths, or "spikes," rather than well-rounded competence, saying the market overpays for balance and underprices talented people who come with real weaknesses. In a public conversation with Ramp co-founder Eric Glyman, Rabois framed Ramp's rapid scale-up around three ingredients he considers universal: disciplined hiring, product execution velocity, and standing out from competitors rather than simply being well-messaged.² He has publicly endorsed promoting from within over hiring outside senior executives, telling a Ramp offsite that the company should stop recruiting outside seniority because its own junior staff were already performing at a high level.² Ramp has said three of its four top leaders were promoted internally rather than hired from outside.¹ His influence since 2013 has run less through founding and running his own company day to day and more through shaping how other founders hire, manage velocity, and build organizations.

Where things stand

As of the mid-2020s, Rabois is a managing director at Khosla Ventures, based in Miami, where he has lived since relocating from the Bay Area in the early 2020s. He continues to sit on the boards of Ramp, Affirm, DoorDash, and other portfolio companies, and remains a frequent public commentator on hiring, startup operations, and venture strategy through talks, interviews, and social media. Opendoor, the company most associated with his own founding credit, remains publicly traded but has faced a materially smaller valuation and business contraction since the housing-market slowdown that began in 2022.

Key facts

• Born in 1969 in Edison, New Jersey; B.A. in political science from Stanford (1991), J.D. from Harvard Law School (1994).
• Held senior roles at PayPal, LinkedIn, and Slide, and served as chief operating officer of Square from 2010 to 2013, resigning after a harassment allegation he denied.
• Co-founded Opendoor in 2014 with Eric Wu, Ian Wong, and JD Ross; the company later went public via SPAC merger in 2020.
• Led Khosla Ventures' first institutional investments in DoorDash, Affirm, and Faire, and invested early in Stripe.
• Left Khosla Ventures for Founders Fund in 2019, co-founded OpenStore in 2021, then returned to Khosla Ventures as managing director in January 2024.
• Known for a publicly circulated "art of hiring" doctrine centered on hiring for narrow talent "spikes" and promoting from within, which he has applied directly in advising portfolio companies such as Ramp.