I imagine cashless exercise is only valuable for ISO options that expire 90 days after leaving? Generally, you'll want to hold your options until the company i

I imagine cashless exercise is only valuable for ISO options that expire 90 days after leaving? Generally, you'll want to hold your options until the company is public or acquired, so you wouldn't need to worry about this. If you are receiving NSOs, it is best to be at a company where they expire 7 years after leaving. Even if you cashlessly exercise, you are still going to have a tax-bill problem, which can be a huge problem if current FMV is far higher than strike.