Once: nothing. (Except a mac mini which the founder was nice enough to buy me as a kind of `exit bonus' :) Despite my options having vested, investors held pre

Once: nothing. (Except a mac mini which the founder was nice enough to buy me as a kind of `exit bonus' :) Despite my options having vested, investors held preferred stock which (since the exit was small-ish) left no liquidity on the table for the employee option-holders. Then, because I was no longer working there at the time of the exit, nothing was negotiated for me as part of the sale. (Those employees who did stay on got something I think, not tonnes though AFAIK and they came with `golden handcuffs'). I had worked hard for them at well below market on the basis the options would make up for my opportunity cost. They didn't, despite the company getting an exit. My advice would be always treat options as a `nice to have' not a replacement for salary, they're so hard to value effectively, and even in the event of an exit their value can still depend to a great extent on the goodwill of founders and investors at the time, on whether you're still working there and whether you want to work for the acquirer, and in general on so many factors outside your control.