> you'll still take home a large payout even after taxes have been deducted, i would not worry about that, would be more worried about when/if the company either goes public or gets acquired.

But they will be on the hook for an AMT bill in April which will likely be worth 3-10 years worth of their current annual salary. The tax question is by far the most important question for this individual. The question of losing the $X0,000 that they put into the options directly is a rounding error.