Unless it was from a Roth you are stuck with short-term capital gains tax rate for a full 12 months. if your stock at 0.57 was invested over a year that really sucks, especially if Nasrat sells the company in 11 months. You would have much much larger tax hit if the sell causes us to have to cash out. If it was already short-term but you had 6 months of investment under your belt you still started the clock over and have 12 months to go.