This is pretty far off topic, but I'll answer it: I merely rode the internet bubble, and cashed out when it was very obvious that we could not sustain the valuation that the market had given us. Actually, had I acted unethically, I could have locked in 2-3 times the amount that I actually did cash out. I made almost all of my money (mid 7 figures pre-tax) on one year of vested stock options that had gone up 14-fold from my strike price. Knowing as I did that we were not possibly going to sustain that valuation, I could have bought an option collar for the 3 additional years of options that had not yet vested by the time our over-valuation became public knowledge - but I didn't, because, as an officer with a fiduciary duty to attempt to maximize our stock's value, I took the position that trading in put options that only would be in the money if our stock price dropped would be a violation of that fiduciary duty.

The surprise was actually on me when I learned how many of my superiors in my own company as well as other officers in other companies within the same industry had done that regardless of their fiduciary responsibility to their shareholders. And frankly, the SEC has only pursued the very largest of these folks - people who's cash-outs were in the 9-figure range who had used option collars to lock substantial gains when they knew full well their stock valuation was higher than would be sustainable.

And yes, I fly in coach, unless I can get an upgrade with an economical expenditure of miles. And no, I was never a salesman - I was a marketing director, and then later a VP of strategic business development - which basically involved using our over-inflated stock as currency in acquiring adjacent technologies and product portfolios to our own.