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What is the tax risk of exercising my employee stock options now ? I left the company in 2018 and they gave me 3 years to exercise. The company is currently private. If I buy the stock now at my low s

 
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What is the tax risk of exercising my employee stock options now ? I left the company in 2018 and they gave me 3 years to exercise. The company is currently private. If I buy the stock now at my low s

You aren't confined to only the "Subject" box when you ask a question in here.  The Subject box is where you post the essential question but down below there's a "Message" box where you can describe all the details behind your question.  Also, this is a forum for discussing income taxes and there's no obvious income tax question in what you've posted.

 

Assuming the "options" refer to NonQualified Stock Options (NQSOs) - which is probably the case - then the risk you face is pretty much the same risk any investor might face when deciding to buy stock, with the added issue that the exercise of the option might create reportable "compensation" income, income that will be taxed. Your basis will be the sum of the cost of exercising plus the compensation (if any) created by the exercise.  In other words, your basis with be the "fair market value" of the stock.

 

Assuming that you exercise and want to keep all of the stock in the grant you'll need to come up with enough cash to cover the withholding taxes and the cost of exercising the option.  At that point you hope, just like any investor, that the company prospers, the stock value rises and you can cash in for a large capital gain.

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