Is There Any Reason to Exercise Before Exit?

Question

Working at a startup that makes something genuinely useful, and it's selling like crazy. Growth is actually tied to revenue, go figure. At current valuation, my options are worth multiples of the strike price.Would you exercise them?

toast0 · Accepted Answer

If your options are ISOs, and you want capital gains treatment, you need to dispose of the shares after the later of two years from grant or one year from exercise. If the (company) exit is a cash deal or not properly structured, when it closes, that could be the date of disposition. And if you hadn't exercised a year before, you get ordinary income treatment.
Of course, exercising an ISO causes current AMT income, so there's probably a current tax year obligation. (That should eventually get resolved). And your stock is illiquid until an exit, which presents risks, of course.
Otherwise, stockholders have more rights than optionholders. Generally mergers and acquisitions need a vote of the shares, although you probably don't hold enough shares to matter, sometimes it's fun to vote. And you would be entitled to more disclosure as well.

livinglist · Answer

I think most of time, the granted options will expire in some period of time if employee quits before exit?