Purchase Stock but cannot pay AMT

Question

I was released by my company and I had to purchase my ISO's within 60 days of leaving the company or lose them. The issue is to purchase them would mean around a $1.2m AMT & State Tax Bill next year. As the company is private they determine if and when they buyback your shares. I want to sell them all now but can't, so if I purchase them all and between now and next year the company don't buy them back I have a Tax Bill that I cannot pay.

Where do I stand when I have no control when I can sell my shares? when I need to sell my shares to pay my tax bill? It will mean selling my house, cars and still not have enough funds to pay my AMT & State Tax thus it will probably bankrupt me?

perennial_noob · Answer

To repeat a standard disclaimer but this is something you should approach a tax consultant with. You already seem to have an estimate of $1.2M (which I'm not sure how you have). The best reference sites are still approximations. Also note, that you pay the higher of AMT and your usual income tax.

As for possibly selling your stocks, you could look into secondary markets to sell - SharesPost, EquityZen, for ex.

Purchase Stock but cannot pay AMT

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