Vinod Khosla is more popular than ever right now. The Sun Microsystems co-founder turned prominent investor — first at Kleiner Perkins and, for the last 20 years, at his venture firm Khosla Ventures — has always been sought after by founders thanks to his no-nonsense advice and his firm’s track record, including bets on Stripe, Square, Affirm, and DoorDash. But a $50 million gamble on OpenAI back in 2019 – when it was far from clear that the outfit would succeed on the scale that it has – put Khosla Ventures, and Khosla himself, squarely in the spotlight.








