Total guesswork as I don't know the guy, but my suspicion as an observer is the money from selling Reddit and Hipmunk was peanuts, he has lots of wealthy friend

Total guesswork as I don't know the guy, but my suspicion as an observer is the money from selling Reddit and Hipmunk was peanuts, he has lots of wealthy friends, and the IPO is a good chance at a big win, despite the downsides.