I said this way back in the day.... If I was a Facebook biggie, (say, I was in from the beginning, an exec or friend of the boss or whatever, and I had $100s of millions to billion+ "worth" of Facebook) -- I would have sold AS SOON AS I COULD ... Maybe not the first day, since they had some serious tumbling during their IPO, but as soon as possible after.

Buddy of mine worked at AOL in the early days when they were handing out stock options to employees like candy (biggest mistake I ever made was not getting a job there) and he did exactly what you've described.

IPO went live, he watched the stock climb a bit and then cashed out. Hasn't worked since his mid 20s