If you left on good terms, assuming your version of "fired" is not as bad as "FIRED!", perhaps you can buy your options at the strick price, but that's risky. I

If you left on good terms, assuming your version of "fired" is not as bad as "FIRED!", perhaps you can buy your options at the strick price, but that's risky. If you buy your options for say $10000 and the stock ends up being worthless then you lost $10000 plus taxes (read on) The AMT Tax Monster: Suppose you buy your options for $10000, and if the startup is acquired or publically traded and your shares are worth $90000 at the end of the year, then the IRS will say that you earned an extra $80000 in short term capital gains ... WHETHER OR NOT YOU SOLD THE STOCK! You still have to pay tax on that change in value. That's a "feature" of the AMT tax. So you pay the IRS an extra $22000 in taxes. You're now down $32000. Finally after 30 months you sell the stock for $38000. So overall you gained $4000 plus and if you know which forms to file you can get a tax deduction for the extra tax you paid before... up to certain amount. So don't buy your options unless you're absolutely certain the stock will be worth a lot more than what you paid for it and you can sell it quickly at any time.