Summary List PlacementKeith Rabois says he decided to invest in Airbnb within three minutes of his first meeting with cofounder Brian Chesky in 2010. "He went into this monologue explaining Airbnb. I interrupted him and said, 'This is the coolest thing I've seen since YouTube, and I need to invest. How do I do that?'" Rabois recounted in an interview with Business Insider. He wrote one of the first checks to the company that year, when the firm was still fresh out of Y Combinator and valued at only $3.5 million. A lot has happened since then.