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The Upside for Wu
If the company is a huge hit and Mr. Wu's options end up being worth a million dollars after ordinary income (not buying them out), he'd keep about $500,000 in The People's Republic of New York; but if he has long-term gain tax treatment on them, he'd keep somewhere around $650,000.
Alternatively, if the company goes bankrupt, he loses everything. So he is making a bet of $12,500 in hopes of saving $150,000 or maybe even more in taxes.
And Mr. Wu is making a big bet on this...
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