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FWIW, re: taxes - TrumpTax raised the AMT thresholds so aggressively that the % of folks to whom this applies is probably a lot smaller than it used to be.

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And even if you are pushed over the AMT threshold, and if the only reason you went over was due to purchase of ISOs, and if you don't go over the threshold in the following year, you can get credit in future years for that extra tax you had to pay.

Correct. You can claw back a chunk every year until you have that AMT paid back so depending on your inflation and investment opportunity cost expectations you are not actually risking that much money, just the cost of the shares.

I think that really speaks volumes to how relevant it is to join early stage if you want to play the options game - later stage companies _seem_ safer but may not actually be that much safer if you consider everyone already in the investment aggressively driving the price of the shares up and forcing you to risk more on exercise.

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