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I'm at a startup and haven't exercised for this exact reason I was hoping this was to fix that.

It's unclear to me that if I defer it and the company goes out of business before then, does that mean I pay no taxes?

And if the price goes up do I pay capital gains or income tax on the difference in value between now and what it went up to? What about the difference between now and my excise price.




In my unprofessional opinion you need to know at least two things to get an idea of whether or not you will owe taxes when you exercise: 1) the strike price you pay to exercise your options, 2) the current fair market value (FMV) of the stock

You will only run into this AMT trap if there is a difference between 1 and 2. This could happen if you were granted options a long time ago and your company has since raised new rounds which increased the valuation. This is when the IRS eyes your exercized options as 'income' unlike the normal case with ISOs where the strike price and FMV are pretty close.

EDIT: see this excellent post elsewhere in this discussion: https://news.ycombinator.com/item?id=12565340


If you never exercise you don't pay taxes.

I think if you hold the shares longer than 2 years, then you pay capital gains. If you hold them less than 2 years, then you pay income tax.




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