Keith Rabois, a managing director at Khosla Ventures and CEO of OpenStore, sat down with Drew Peterson (MSB’25) at Georgetown’s 2025 Venture in the Capital Conference. Rabois held leadership roles at PayPal, LinkedIn and Square and has served on the boards of companies including Yelp and Reddit.
Rabois discussed how his legal training helped him judge risk, including in his early angel investment in YouTube, while arguing that the lawyer’s habit of spotting everything that can go wrong can work against a venture investor. He explained why Square shared meeting notes companywide, saying people make smart decisions only when they have all the information. He also shared why he does not rely on asking consumers what they want, what he thinks makes a company ready to go public, and how Washington is drawing more technology leaders. For aspiring investors, he stressed developing a clear answer to the question “why me.”