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ISOs · Case studies
Illustrative scenarios, start to finish.
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Case study: exercising pre-IPO ISOs
An early employee exercised before the IPO and made an AMT bet that paid off. The lesson is in why it worked, not that it did.
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Case study: the AMT trap when the stock crashed
A worker owed AMT on a paper gain, then the shares fell 70%. Here is what he did next and what would have saved him.
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Case study: a disqualifying ISO sale to diversify fast
Why one founder chose ordinary income over holding a single volatile stock for the lower rate.
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Case study: the 90-day scramble after leaving
An employee left with $90k of in-the-money ISOs and 90 days to find the cash, or lose them.
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Case study: what happens to ISOs in an acquisition or IPO
A liquidity event finally lets you sell, and that is exactly when ISO holders make their most expensive mistakes. The money showing up is not the same as the money you keep.
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