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.