I think jwz sums it up best in another post, where he talks about the best case scenario: becoming rich from your startup:
I've known dozens of instant-millionaires so far (from Netscape as well as other companies), and basically, I don't speak to any of them any more, because the money changed them and turned them into fairly creepy people. People who spend $10k on a wristwatch and then brag about it (while trying to aloofly sound like they're not bragging about it.) People whose sense of self-worth has gone nonlinear, because when they look at their brokerage statement, they forget that, while skill was certainly a component of why they got to where they did, luck was also a huge component. Most of these people have never worked for a company that built a good product and failed anyway. They don't have any understanding of the fact that skill is often necessary, but always insufficient. They believe their hype.