Rabois invested in Yelp and the Xoom Corporation prior to each company's initial public offering (IPO).

[2][3][4] Rabois has been involved in investments in YouTube, Palantir Technologies, Lyft, Airbnb, Eventbrite, wish.com,[5] Relcy[6] and theorg.com.

Rabois stated that the incident was designed to challenge Stanford's rules on student speech.

[12][13][14] Thiel later defended Rabois in his book, The Diversity Myth: Multiculturalism and Political Intolerance on Campus.

After some unsuccessful ventures, in 2010, Rabois joined Square, a company that provides an electronic payment service, as its Chief Operating Officer (COO).

[22][23] In January 2015, Rabois joined the board of directors of Scribd as an observer after Khosla Ventures led a new investment round in the company.

[26][27][28] In 2021 while at Founders Fund Rabois co-founded Miami-based OpenStore, a retail-holding startup that acquire brands in the Shopify ecosystem.

[30] Rabois left Founders Fund in January 2024 to rejoin Khosla Ventures, but continues to represent it on the boards of Ramp, Found, and Trade Republic.

He planned a renovation that included a new penthouse level, a basketball court, lockers and a sauna, but received pushback from six of his neighbors.