I want to keep my equity. I have NSOs, and would have to execute within 90 days of leaving. I think there's a decent chance it will be worth a decent amount of money in the next few years. I don't plan to execute with my own money, as the cost to do so is ~100k. I also don't think there's any chance I could execute with a loan or anything like that.
I plan to ask for an extension of the 90 days to execute. If it's extended, I would stay at the company for 6 months or so to allow for a smooth transition. If it's not extended, I would leave immediately.
I'm a key employee. If I were to leave abruptly, it would likely serious cause problems for the company.
Am I crazy? Should I be asking for something else in order to keep my equity?
2. It's a startup and you say you're a key employee. Why do you have NSOs vs ISOs? NSOs are very unfavorably taxed -- read up on NSOs vs. ISOs before anything else.
3. Perhaps you can stay on as a very part-time advisor to postpone start of 90-day window? (so you can start your next thing instead of staying 6 months)
4. Don't join another startup unless they offer you ISOs, and are an early enough employee that you can exercise early and elect 83(b). Or unless they pay you more than BigCo.