# Keith Rabois

> Keith Rabois is a PayPal Mafia veteran, co-founder of Opendoor, and Managing Director at Khosla Ventures whose career spans law clerk, corporate attorney, political adviser, and now one of Silicon Valley's most prolific — and outspoken — investors. He is the first institutional backer of DoorDash, Affirm, and Faire, made early bets on Stripe, YouTube, and Airbnb, and brought the iBuyer model to residential real estate before moving to Miami and catalyzing one of the biggest tech migration waves in recent memory.

- **Role:** Managing Director at Khosla Ventures; Chairman of Opendoor
- **Organizations:** Khosla Ventures, Opendoor, OpenStore, PayPal, LinkedIn, Square, Slide, Founders Fund
- **From:** Edison, New Jersey, USA
- **Nationality:** American
- **Education:** B.A. in Political Science, Stanford University, J.D. (with honors), Harvard Law School
- **Known for:** Member of the PayPal Mafia — alumni network that founded/funded dozens of dominant tech companies, First institutional investor in DoorDash, Affirm, and Faire, Early investor in Stripe, YouTube, Airbnb, Palantir, Lyft

## Career timeline

- **1994-1995** — Law Clerk, U.S. Court of Appeals, Fifth Circuit
- **1995-1999** — Attorney at Sullivan & Cromwell law firm
- **1999** — Political adviser to Dan Quayle's 2000 presidential campaign
- **2000-2002** — EVP Business Development & Policy at PayPal (acquired by eBay for $1.5B in 2002)
- **2005-2007** — VP Business Development at LinkedIn (joined as 20th employee)
- **2007-2010** — EVP Strategy at Slide (social gaming, founded by Max Levchin)
- **2010-2013** — COO at Square; resigned amid controversy in January 2013
- **2013-2019** — Partner/Managing Director at Khosla Ventures; led investments in DoorDash, Affirm, Faire
- **2014** — Co-founded Opendoor with Eric Wu and JD Ross; pioneered iBuyer model
- **2019-2024** — General Partner at Founders Fund (Peter Thiel's fund)
- **2021** — Co-founded OpenStore, Miami-based Shopify brand aggregator (raised $75M, later crashed 95% in valuation)
- **2024-present** — Managing Director at Khosla Ventures (returned January 2024)
- **2025-present** — Chairman of Opendoor (returned September 2025)

## Achievements

- Member of the PayPal Mafia — alumni network that founded/funded dozens of dominant tech companies
- First institutional investor in DoorDash, Affirm, and Faire
- Early investor in Stripe, YouTube, Airbnb, Palantir, Lyft
- Forbes Midas List ranked as high as #4 in the U.S. and #8 globally
- Co-founded Opendoor, which pioneered the iBuyer model in residential real estate and went public in 2020
- 15+ portfolio companies have gone public
- 73+ investments with 42+ exits
- Delivered iconic 'How to Operate' lecture in Stanford/YC startup course (2014) — one of the most-referenced startup management talks online
- Catalyzed the tech migration to Miami (2020-2021) through public advocacy and Twitter presence
- Net worth estimated at ~$1 billion

## Latest updates

- **2026-02** — Joined board of Comp AI after Khosla Ventures led $17.25M Series A for the HR compensation startup
- **2026-01** — Publicly disavowed by Khosla Ventures founder Vinod Khosla over X posts defending ICE shooting of American citizen
- **2025-09** — Named Chairman of Opendoor after former Shopify COO Kaz Nejatian appointed CEO; publicly called for 85% workforce reduction
- **2025-04** — Led $11.5M Series A for Roam, a startup focused on assumable mortgages, calling it 'the future of the housing market'
- **2025-02** — Listed Miami Beach waterfront home (purchased for $28.9M) for $65M as couple prepared to move to Washington D.C.
- **2024-01** — Returned to Khosla Ventures as Managing Director after five years at Founders Fund

## Links

- LinkedIn: https://www.linkedin.com/in/keith/
- Twitter/X: https://x.com/rabois

---

Profile page: https://yespress.io/keith-rabois
Published by YesPress — https://yespress.io
Last updated: 2026-04-29