El Guapo wrote: Wed Nov 15, 2017 1:01 pmI mean, it's just not true that the only way to determine the value of a vested option is to sell it.
It's the only valid way of calculating the *actual* gain to the employee.
Some maths:
Employee A is granted 2500 stock options for XYZ, Inc with a 4-yr vesting schedule (25% per year), and an expiration date of 8 years (from the grant date), which also expire 30 days after separation. The strike price is $5 per share (in my experience, the strike price has always been set by the closing price of the stock on the day that the Board approved the grant).
On the first year anniversary, the stock price is $7 per share. Since 625 shares have now vested, Employee A owes federal income tax on $1250. On the second anniversary, the stock price is $12 per share. 625 shares have vested on this date, so Employee A owes federal income tax on $4375. What about the stock options that vested the year before at $7 that Employee A didn't exercise? Does she owe federal income tax on the additional $3125 that those options are "worth" on the second anniversary date? On the third anniversary, the stock has taken a hit and is now trading at $4. Employee A gets to take a loss on the -$625 "worth" of options? What about the first 1250 options that are now worthless that they already paid taxes on? On the fourth anniversary, the stock has recovered and sits at $6, when the remaining options vest. That's federal tax on $625, and whatever we have to do with the other 1875 options that have been treated differently because they vested at different times.
Things seem to be going well for the XYZ, so Employee A holds onto the options. Then Lehman Brothers fails, and the stock market crashes in the span of a day, and while she tried to sell them she realized that you can't do that without a margin account which takes too long to setup and the stock falls to $2.89 per share and all of her options are now worthless. Oh, and she's laid off while the stock is depressed, and all 2500 options expire.
You *could* do this. It would just be monumentally stupid to force Employee A to have to pay income taxes on $5625 of income that the employee never received.
What if in this scenario, the employee held the options for a further three years (selling seven years after the original grant), at $17 per share? You've now got four lots of options that have been taxed one or more times over the past seven years, that all have to be treated differently when trying to calculate how much tax is owed.
That's scenario #2 described above.
Scenario #3 is ($17 - $5) * 2500 = $30,000. Now pay income tax on it. Done.
The idea that this is a problem that needs solving is preposterous.