The first startup I worked for, back in the Ancient Days Of The Web, gave me (employee #4, 5, or 6, depending on which of the three of us walked in the door fir

The first startup I worked for, back in the Ancient Days Of The Web, gave me (employee #4, 5, or 6, depending on which of the three of us walked in the door first) options that would have netted me low seven figures when the company was gobbled up in the first bubble. Would have, had I exercised those options before I quit the place and let them expire. So it goes. The second time I had equity was a few years later, joining a much larger company shortly before a terribly botched IPO. The next morning the CEO parked his new Ferrari right next to the employee entrance; the rest of us were stuck with a strike price well above the current valuation. My options eventually peaked out at ~$300K value, but were underwater for years; in theory I could have made far more just buying the stock like any old yutz off the street, if I'd had any expectation that the company would recover, which I didn't. The third time, well, ask me again in a couple years and we'll see how it turns out. It'd be nice, of course, but I'm not counting on it. My advice: * Be an early employee, preferably during a bubble. (Now is probably good.) * Exercise your options. * Never park your shiny new sports car where your employees can see it.