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I was granted an employee stock option about two years ago. Almost half of it has vested.

The company I am with is doing very well. Every month a little more of my option vests. I have not exercised the option yet.

I believe the company will do very well in the future and want to exercise the vested shares and exercise the newly vested shares each month as they vest.

Is this possible or is a stock option only allowed to be exercised once?

The reason I want to exercise as soon as I can is to start the clock on long term capital gains and avoid paying AMT tax as the FMV of our shares increases.

The only thing I can find in my contract that seems relevant to this is a passage that says, "You may exercise the vested portion of your option during its term by delivering a Notice of Exercise to the company..."

It would be ideal if I could exercise my option as many times as I wanted but would like to be sure before diving in and potentially forfeiting the unvested shares.

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    Just to be clear, any "one particular option" you of course can only exercise once (unless I misunderstand something about the QA?) I assume OP you mean, say you have "10" options, you want to do 2 one time, 2 another time, 2 another time and so on. Is that correct? – Fattie Nov 6 '18 at 9:25
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Is this possible or is a stock option only allowed to be exercised once?

You would need to check with your company. Generally there is no restriction of exercising the option. At times some companies to manage logistics may have allowed windows "x" number of times a year to exercise the vested options. This would be best advised by your company.

It would be ideal if I could exercise my option as many times as I wanted but would like to be sure before diving in and potentially forfeiting the unvested shares.

It is unlikely that you will forfeit unvested shares because you exercised the option on vested shares. Check your agreement, generally the unvested shares are forfeited in certain conditions like; you are no longer in employment, or other such clauses.

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