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Incentive Stock Option (ISO) tax question - more specific this time
Alternatively you could exercise 12000 shares for $36000 and immediately sell 7200 shares to recover your exercise price. Then you use the remaining 4800 share to pay the exercise price of the remaining 8000 options. Both scenarios are equivalent but may have different fees associated, so it's worth checking the fine print.  Tax wise: The above example is "cash neutral before taxes". The taxes associated with these transaction are substantial, so it's highly recommended to talk with a tax adviser. "cash neutral after taxes" depends highly on your specific tax situation.