Anyone considering a “developer #1” position at a (presumably pre-money, low valuation) company is well-advised to insist on pre-exercising their options to avo

Anyone considering a “developer #1” position at a (presumably pre-money, low valuation) company is well-advised to insist on pre-exercising their options to avoid exactly this conundrum. You should even be able to get the cost covered with a signing bonus, since the company will get the cash right back. Then you can quit any time and keep all your vested shares, with no tax consequences. Worked out swell for me. Consult a real tax attorney, of course.