Cashless stock option exercise help!

Not just ordinary income but (if he's an employee), W-2 wage income, and I believe it'll be subject to SS (to the cap) and Medicare tax.

No, it won't. For an NQO, it is exercise that triggers income, not the subsequent sale.

Since this is a NQO, it goes like this:

• Bargain element is taxed as wages *upon exercise*.

• Stock basis is exercise price plus recognized wage income.

So for BOTH scenarios, he'll be in the following situation:

• 5,000 of wage income

• Will receive stock with a basis of 5,000.

In scenario one, he'll have $225,000 of wage income and a minimal short-term capital gain or loss to the extent that what the stock sells for is different than $425,000 (since it's a same-day sale, we'd expect the stock to sell for about the same price that is used by his employer to calculate the recognized wage income).

In scenario two, he'll have $225,000 of wage income and then a long-term capital gain to the extent that what the stock sells for is different than $425,000. Exercise and hold WILL NOT convert the wage income to capital gain.

Thanks Rich,

I finally found Pub 525 about 30 seconds after I posted this. Everyone ignore my OP, its completely wrong.

My new understanding is that non-qualified stock options are treated as ordinary income at the time the option is exercised on the difference in market price and grant price (EVEN if the stock is not sold). Basis is then adjusted to current market price for determining gains (either long or short) on the future sale of the stock.

That rule (and the ignorance of such) has indeed caused major financial problems for many silicon valley newly minted paper-rich folks in 2000, when their stock options turned to negative and they ended up owing to the IRS on worthless paper.

Here's one such sobering story.

's about ISOs (Incentive Stock Options) where there isan advantage to exercising and holding as opposed to NQswhere there is no such advantage (which is what the OP wasasking about). The AMT from exercising ISOs is whataffected most people in Silicon Valley. With NQ is thereis no advantage to exercising and holding; one mightas well just wait to exercise and sell if one really thinksthat the stock will keep appreciating. Anoop

In case it's not clear, the issue surrounding the Options is this; Upon exercising, one has a windfall of ordinary income, say $250K to keep the numbers low. Now, if the stock crashed, and many did, you have a capital loss of say $200K. Well, you can only take stock losses to match gains, up to $3000 that you can take off regular income, so in my example, taxes must be paid on $247K, even if the stock is zero. The losses carry forward, $3,000/yr or against other stock gains. I read a story about such a man who found a woman with a $200,000 gain, and got married. (The numbers were higher, more like in the millions, but the story doesn't change). JOE

Nope, not clear. As anoop wrote, it is the issue with ISO's and AMT that is the nasty one that affected people back in 2000. It generates an AMT deferral item which may or may not ever be recaptured.

The issue you describe is easily avoided by exercising and selling, since there is no incentive to hold the stock, as there is with ISO's. What you are describing is the same as someone getting a $250K cash bonus from their employer and immediately investing it all in one loser stock - why would someone do that on purpose?

-Mark Bole

What Mark said. Exercise and sell that day. The question is simply when to exercise, which depends on the cash needs of the owner and the prospects for the company. AMT can kill you. Don't risk it. Joe Weinstein

The OP is talking about NQOs, so AMT isn't an issue.

Rich is right, NQSOs not ISOs.

We did opt to exercise and sell by the way. The employee no longer works for the grantee and the options were set to expire Feb. 1, 2007.

thanks all

Exactly -- just to clarify some previous replies which were evidently confusing the two.

-Mark Bole