Good question. To clarify: I cashed out 1/3 because I'm inherently conservative financially and had no idea whether the stock would go up or down. Not because of tax purposes.
My colleagues who ran into problems with Uncle Sugar are the ones who bought and held their stock for less than a year (but long enough for it to tank in value), didn't make estimated tax payments and were fined by the IRS, or otherwise made decisions based on irrational exuberance, like borrowing against their options to buy jet-skis and crap.
My colleagues who ran into problems with Uncle Sugar are the ones who bought and held their stock for less than a year (but long enough for it to tank in value), didn't make estimated tax payments and were fined by the IRS, or otherwise made decisions based on irrational exuberance, like borrowing against their options to buy jet-skis and crap.
Hope this answers your question.