jman25

Isn't it sale date 2 years from grant, not exercise date 2 years from grant, that matters for ISO vs NSO treatment? "Instead, if the employee holds the shares for two years after grant and one year after exercise, the employee only pays capital gains tax on the ultimate difference between the exercise and sale price. If these conditions are not met, then the options are taxed like a non-qualified option" from https://www.nceo.org/articles/stock-options-alternative-mini...

Honestly, if you do care about money at least in the sense of relatively short-term cash, I'd recommend trying to solve it by shooting for something Google-caliber.