Thursday, March 20, 2014 11:47:39 PM
He bought a million shares last year at .08 (call it block A)
He exercise half a million shares of company grant stock option at .08 (call it block B)
The half a million shares he sold at .28 will be counted against his purchase last year (block A). This will be counted as capital gain instead of income.
For block B, if he does not sell for more than a year, it will qualify for capital gain rate also.
So why sell now? As you say, he needs the cash to exercise the stock option and pay income tax due in april.
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