I've had options at 3 companies that all went through some event. 1 - Company acquired after I left. I paid 3k for my shares when I left, made 3k net. Not bad.

I've had options at 3 companies that all went through some event. 1 - Company acquired after I left. I paid 3k for my shares when I left, made 3k net. Not bad. 2 - Company was self-funded when I left, paid about 2k for shares. When they took external investment years later, I needed to sell my shares, net 6k. 3 - Company I was still working for was acquired. I'm acquihired at a better salary & benefits, plus retention bonus after a year. Exercised my options at 4k to net 55k. I've had a run of good luck, and, in each case, the cost to exercise my options was one I could afford to lose if things turned. If it comes up again, I'll have to evaluate where I am at that time. Each event is unique, you have to judge your specific circumstances.