The thing is, most support agents only get a few shares. Both of the last two companies I worked for, it cost me about $1,500 to exercise the shares I'd vested

The thing is, most support agents only get a few shares. Both of the last two companies I worked for, it cost me about $1,500 to exercise the shares I'd vested after about 2 years, and their 409a FMV was about $26k at the time I exercised them. One of those companies has since gone public and my piddly little $1,500 became worth over half a million dollars. It's absolutely a lottery, but if you get in places at the right times, I think it's worth collecting tickets rather than doing the same work for similar pay where you don't get tickets.