Michael Gray, CPA’s Option Alert #57

An irregular alert for issues relating to employee stock options

July 3, 2008
© 2008 by Michael Gray, CPA
ISSN 1931-2768

(If you find this information valuable, please pass it on to a colleague!)

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Happy July 4!

Hope you and your family enjoy a great July 4! We get a three-day weekend this year.

Be extra careful with fireworks, this year. If you live in California, you know there are many wildfires burning throughout the state. There might not be many firefighters available for emergencies right now.

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Can you believe the year is half over already?

How is your year going? Despite all the “doom and gloom” talk in the press, we hope this has been a good year for you. Let us know if we can be of service for any developments.

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Michael Gray gives a live employee stock options seminar on July 11

Michael Gray will be giving a live “Secrets of Tax Planning For Employee Stock Options” luncheon seminar on July 11. The seminar will be at Hobee’s Restaurant at the Pruneyard in Campbell, California. For details and to make reservations, call Dawn Siemer weekday afternoons at 408-918-3162, or email mgray@taxtrimmers.com.

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Have a great vacation, Dawn!

Dawn Siemer will be taking a vacation visiting family in the Northwest from July 14, returning July 28. Dawn manages our internet operations and our office and she will be sorely missed while she’s away.

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Employer reporting for payment of deductible ESOP dividends to change

Certain dividends paid directly to employees relating to employer stock held in an ESOP are tax deductible for the employer.

The dividends are taxed as retirement plan distributions, but they aren’t eligible for rollovers and they don’t count as required minimum distributions.

In the past, employers have reported these payments on Form 1099- DIV. This practice started in 1985 to allow taxpayers using short form 1040A to report the income.

Effective for distributions of these § 404(k) dividends made in 2009 and later years, the payments will be reported on Form 1099- R. If other qualified distributions are made in the same year, they will be reported on a separate Form 1099-R from the § 404(k) dividends.

(IRS Announcement 2008-56, 2008-26 IRB)

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Questions and Answers

To our readers:

The answers to many of your questions can be found in our free reports, “Executive Tax and Financial Planning For Non-Qualified Stock Options” and “Executive Tax and Financial Planning For Incentive Stock Options.”


Is there a difference between nonstatutory and non-qualified stock options?


No. They are two names for the same thing.


I can exercise an option by swapping NQ shares already held from a previous exercise, according to my employer. They tell me also that I can swap some additional shares to cover the withholding taxes on the new shares. Will surrendering the additional shares to pay taxes also be tax free?


No. You will be deemed to have sold the shares to pay the taxes.

Is there a reason you are holding onto shares received from exercising an NQO? Unless the shares can’t be sold or there is an expected IPO or acquisition, I usually recommend selling them. The taxes could then be paid using the sale proceeds. You might also be able to sell shares received to pay the exercise price.

Michael Gray regrets he can no longer answer emails personally. He will answer selected questions in this newsletter.

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Do you know about our other newsletters?

For general tax developments, tax planning ideas, business development ideas and book reviews, subscribe to Michael Gray, CPA’s Tax & Business Insight.

We are now offering our real estate tax newsletter, Michael Gray, CPA’s Real Estate Tax Letter, free of charge. Like this newsletter, we will talk about new developments, have reports on special tax concerns, and answer questions and answers. To subscribe and read a sample issue, visit realestatetaxletter.com.

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IRS Circular 230 Disclosure:

As required by U.S. Treasury Regulations, you are hereby advised that any written tax advice contained in this communication 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.

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Consult with a tax advisor

For our readers who aren’t tax advisors, this newsletter is intended to alert you about tax issues that could affect you. It is not a substitute for advice from a professional tax advisor. You will find that getting advice from a qualified advisor is a worthwhile investment.

Tax advisors should view the newsletter as an alert to become aware of issues relating to employee stock options for further research and study.

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Subscribe to Michael Gray, CPA’s Option Alert!

To receive the next issue of Michael Gray, CPA’s Option Alert with more employee stock option tax developments and answers to questions from our readers automatically via email, subscribe by filling out the form below.

(Michael Gray is the author of Secrets of Tax Planning For Employee Stock Options, Stock Grants and ESOPs.)

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