My first rodeo, my existing options were worth about $40k on buyout day. That's chump change, even counting inflation, but I was a kid so that more than doubled my assets. Everybody was pretty happy. Five months later we were all almost under water, and half our raises were more stock options (I don't know what kind of psychadelic drugs come up with that plan). Nobody was happy and productivity tanked. And still we were doing a better job than our new masters. By the end of the lockup period our options were worth 60% of the strike price.
In the end I learned the hard way about a bizarre strategy for keeping your company going. First, have a high valuation. Second, find a small company with liquid assets. Third, buy out the company with a stock swap and only a little cash. And now you have more capital on hand so you can lie to your investors for a few extra months.
Not that I'm bitter.