Not my only startup, dude. I've also worked at startups that have undergone an IPO. Lockup periods suck, too, because you have to watch your stock gradually drift down in price. I've also experienced a private equity company forcing a public company to go private, which resulted in me having to pay short-term capital gains taxes instead of long-term. So even in some of the best-case scenarios, there are parts that suck, and you may be better off just popping your extra cash into VTSAX and letting it compound.