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Date:   Wed, 14 Jul 1999
From:   Greg

I have received confusing information on the exercise of employee ISO options. Is the $100,000 annual limit on the number that can be initially exercised in a year or the maximum that can be exercised in a year or both. For example, if I was granted $100,000 worth in each of three consecutive years, could I exercise all $300,000 in one year, hold for a year, and only pay long term capital gains (ex AMT implications)?

TIA,
Greg

Answer

Date:   Wed, 28 Jul 1999

Hello Greg,

Thanks for writing.

The rule is the maximum fair market value of stock that is exercisable for the first time by any individual during a calendar year is $100,000. The fair market value of the shares is determined on the date of grant. Any options in excess of this amount that are exercisable during the calendar year are treated as non-qualified stock options. The earliest-granted options will be treated as incentive stock options. (Internal Revenue Code Section 422(d).)

Since your example is framed based on when the options were granted, I can’t say what the result will be.

However, if $100,000 worth of options are exercisable in three consecutive years, you could exercise $300,000 worth in year three and eventually qualify for long-term capital gains treatment for the regular tax.

Good luck!

Mike Gray

For more information about incentive stock options, request our free report, Incentive Stock Options - Executive Tax and Financial Planning Strategies.

IRS Circular 230 Disclosure: As required by U.S. Treasury Regulations, you are hereby advised that any written tax advice contained in this answer was not written or intended to be used (and cannot be used) by any taxpayer for the purpose of avoiding penalties that may be imposed under the U.S. Internal Revenue Code.