Three Ways To Avoid Tax Problems When You Exercise Options

34210643I love the movie Wall Street because Gordon Gekko’s single-minded pursuit of money led to his downfall. This is not just a Hollywood story. In my past role as a tax accountant in Silicon Valley, I saw many executives and employees get greedy, too. By attempting to capture an early gain in their company’s stock, they exercised so many stock options that they didn’t have enough money to pay the taxes due on their gains.

A surprisingly large number of people fall into this trap. Some of them are just ill-informed. Others, I believe, are overcome by their greed: It causes them to forget that stock prices can go down as well as up, or keeps them from embracing a rational plan to pay the taxes.

Up A Creek

In most cases, when you exercise your options, income taxes will be due on the excess of the option value (set either by the company’s board of directors, if it is private, or by the market, if it is public) over its exercise price.

If you have non-qualified options (“Non quals” or NQOs), your employer must withhold taxes when you exercise your options, as if you had received a cash bonus. The employer decides how much to withhold, based on guidelines from the IRS and the states. Unless you sell stock at the time of exercise to cover your withholding, you will have to write a check to your employer for the taxes withheld.

If you have incentive stock options (ISOs), your employer will not withhold taxes. That means it’s up to you to self-regulate and set aside the taxes you’ll owe.

Whether you have NQOs or ISOs, you will need to set aside money held in another account, like a savings or money market account, to pay taxes.

Whether you have NQOs or ISOs, you will need to set aside money held in another account, like a savings or money market account, to pay taxes. If you don’t have the resources to pay the tax due on an option exercise, you should consider exercising fewer options so you don’t create an income tax obligation you can’t afford to pay.

Following are two scenarios that show what can happen if you get greedy and exercise as many options (either non-quals or ISOs) as you can without a plan. You might find yourself in a financial quagmire, stuck owing more in taxes than you have cash on hand to pay.


You exercise a non-qualified stock option when its value is $110 and your exercise price is $10.

Your taxable compensation income is $100.

Assume you are in the highest federal and state income tax brackets, so you owe 50% of the gain to the government.

Your tax on the exercise is $50. You’ll write a check to your employer for the $35 of federal and state taxes the company must withhold. You still owe $15 in taxes.

At this point you own stock in your employer, you’ve paid $10 to exercise options, and $35 for tax withholding.

What happens next?

The stock price drops to $10, at which time you sell your stock.

The final result is you have no stock, have spent $35 for taxes and still owe $15 in taxes (the $10 to exercise NQO and $10 from stock sale net to zero).

Put enough zeros behind these numbers, and you can see how this becomes a problem.

Yes, the $100 loss on the stock sale is tax deductible, but it is a capital loss. The loss deduction may be subject to annual limits, so your tax savings may not be realized for many years.


You exercise an ISO when its value is $110 and your exercise price is $10.

You have no taxable income for regular tax purposes and $100 taxable income for Alternative Minimum Tax  (AMT) purposes. The exercise of the ISO will likely cause you to be subject to AMT for federal purposes and may cause you to be subject to the AMT for state purposes, so assume you owe 35% of the gain to the government.

Therefore your tax on the exercise is $35, and since employers don’t withhold taxes on ISO exercises you must be prepared to pay this $35 from your own resources.

At this point you own stock in your employer, you’ve paid $10 to exercise options, and have a $35 tax obligation.

What happens next?

The stock price drops to $10, at which time you sell your stock.

The final result is you have no stock, but you still owe $35 in taxes (the $10 to exercise ISOs and $10 from stock sale net to zero).

It was in the cases of ISOs[1] that I more often saw people in IRS nightmares, with tax bills in the hundreds of thousands or even millions they couldn’t pay.

As in the case of non-qual exercises, the $100 loss is tax deductible, but may be subject to annual limits.  Also note that you will have a different basis in your stock for regular tax and AMT purposes, as well as an AMT credit carryover, which should be taken into consideration.

Do these scenarios sound unlikely? I have seen versions of them happen dozens of times, often enough that I tell this cautionary tale whenever I can.

What can be done to avoid a potential problem?

• If your employer is public, consider selling at least enough stock at exercise to pay for your ultimate tax liability. This is commonly referred to as a cashless exercise. On exercise, you immediately sell enough stock to pay both the exercise price and your anticipated tax liability. (But remember that you should still set aside some money for the incremental tax due).

If you don’t have enough to pay the taxes, consider exercising fewer options.

• Exercise fewer options so that you keep money aside to pay taxes. This is the hardest choice for many people to make, because they worry that if they don’t act now, that they will have missed a potential big opportunity.

• Consider exercising your options in a staggered fashion. If you hold stock from previously exercised options, that gives you the opportunity to sell the stock as you exercise additional options. This choice can be particularly beneficial if stock has been held for over one year and the associated gain qualifies for favorable long-term capital gain tax treatment.

Manage Your Downside Risk

Be just as rational when it comes to your options as you are when you are planning your investment portfolio. Stock values don’t always increase over time. Part of what you’re doing is managing downside risks. That may mean parting with some of the potential upside to avoid a catastrophic downside.

Being greedy, or unprepared, and betting all of your assets on the future of your employer’s stock can produce some unexpected and undesirable financial consequences.

For more on employee stock options, visit our Stock Options & RSUs section.


Bob Guenley was a tax accountant to Silicon Valley executives from the 1980s through the 2000s, and currently works for a leading venture capital firm.



This article is not intended as tax advice, and Wealthfront does not represent in any manner that the outcomes described herein will result in any particular tax consequence. Prospective investors should confer with their personal tax advisors regarding the tax consequences based on their particular circumstances. Wealthfront assumes no responsibility for the tax consequences to any investor of any transaction.

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13 Responses to “Three Ways To Avoid Tax Problems When You Exercise Options”

  1. tm June 12, 2013 at 10:04 am #

    “In most cases, when you exercise your options, income taxes will be due on the excess of the option value over its exercise price.”

    Can you write off the loss if your exercise price is below the option value? E.g. buying the options for $10 when they are currently valued at $5?

    • Andy Rachleff June 12, 2013 at 11:55 am #

      Why would you exercise options that are under water?

      • Antonio July 3, 2013 at 11:34 am #

        I’d also like to know what would be the point if exercising the option and not selling the stock immediately? Why not hold on to the option and exercise when you want to sell, paying taxes at that time.

        • Andy Rachleff July 5, 2013 at 9:58 am #

          The reason some people choose not to sell immediately is to have the opportunity to get long term tax treatment on their gain if they hold the exercised option for more than one year. Most people do not choose this path because they need the proceeds to pay the tax that is due upon exercise.

  2. Bob Guenley June 12, 2013 at 1:49 pm #

    The direct answer to your question is no. You don’t have a deductible tax loss when you exercise. You have to sell stock to recognize a loss. The bigger question is the one Andy just asked. Bob

  3. Phil Haslett June 28, 2013 at 10:49 am #

    Very helpful post. I’ve found that it’s very difficult to find clear-cut information regarding exercising private company stock options. Private companies should provide more guidance to their employees about ISO vs NQSO vs RSU, valuation, and liquidity opportunities.

    It’s tough for a startup employee to commit to exercising their shares when it requires upfront cash AND they don’t know what they could do with their shares afterwards.

  4. CW September 26, 2013 at 10:27 pm #

    Here is a scenario I am not sure of so if anyone could shed some light that would be great. If I exercise 1000 shares at an exercise price of $10 when company stock was trading at $50, I would have an AMT on $40,000. So let’s say I owe $14,000 ($40,000*.35) on April 15, 2014. I exercised on July 1st, 2013 so my goal is to wait at least until July 2nd, 2014. On July 2nd, 2014 the stock is worth $40 (down 10 from exercise price) and I sell 1000 shares. My profits would be $30,000 (1000 * (40-10)) and my long term capital gains tax would be $4,500 ($30,000*.15). What happens to the difference between the AMT tax of $14,000 and my long term capital gains tax of $4,500?

    Thanks in advance

    • Andy Rachleff September 27, 2013 at 11:07 am #

      I’ll make this as simple as I can:

      -the AMT paid in 2013 is a creditable tax that can be carried forward to following years & reduces your Regular Tax (“RT”) down to your AMT for that year, but not below. Any unused credit is carried forward indefinitely
      -the stock basis for AMT purposes is $50K & for RT purposes is $10K
      -In 2014 you’ll have a $10K LOSS for AMT purposes & $30K gain for RT purposes, so it is highly likely that your RT will exceed your AMT, so you reduce your RT down to AMT

      For example, if in year of sale the RT is $20K & AMT is $12K you use $8K of AMT credit (so tax paid for year is $12K) & still have $6K credit ($14K – $8K) to carryover & in use future years.

      In theory over time you’ll get the $14K back, generally most of which would occur when you sell stock you’ve exercised.

      Where you can get screwed is when your AMT loss is greater than you are allowed to take each year (the annual limit on net capital losses is $3K for both RT & AMT, with any excess being carried over to future years). So in his example, even though he has a $10K AMT loss only $3K is allowed in 2014, 2015 & 2016, & $1K in 2017, so it may take several years to recover the AMT paid in 2013.

      Clear as mud?

  5. mtrono March 4, 2014 at 4:53 pm #

    I’m curious why you didn’t describe a 4th option – cashless exercise & sell everything (or almost everything) that’s vested? This is the lowest risk option (of course, it also has the largest tax liability). This seems like a sensible strategy for individuals whose majority net worth is held in the vested ISO options. You can always decide from that point forward to use some of the proceeds to exercise & hold ISOs as they vest. This leads to your 3rd option.

    The 2nd option seems to me the most risky as it assumes the stock will increase. There’s no benefit if the stock is stable (or grows slowly), but huge opportunity cost if the stock decreases.

    • Andy Rachleff March 5, 2014 at 2:44 pm #

      The article was focused on private company employees who do not have the option of a cash less exercise.

  6. Oliver Channing August 23, 2014 at 1:38 pm #

    Here is my scenario (and I am very confused on this amt credit things).

    I started a job in april 2011 and got 40000 ISO. 1.87 strike price.

    In Nov 2012 I bought 5000 shares at 1.87 (fmv 4.47). Thus paid a little bit of AMT
    In April 2013 I bought 8000 shares at 1.87 (fmv 4.47).
    In Nov 2013 I bought 8000 shares at 1.87 (fmv 4.47). I got hit much harder on amt for this year.

    I recently did a private sale of my 1000 shares at $11 a share. Transfer fees of $6250. I sold
    from the lots that were considered long term cap gains.

    My question/confusion is what my cost basis is for irs reporting. It the cost basis on my stock the 1.87 or is it the 4.47. I assume that it is actually 1.87 and I would pay LTCG on that, and *then* some of my prior AMT payments would be payed back?!? This feels in some ways like a double taxation thing. I paid some tax on virtual gains but then have to pay my long term cap gains on the original cost basis. Any clarifications would be great.


  7. Oliver Channing August 23, 2014 at 1:39 pm #

    The above comment actually was 10,000 shares at $11 dollars. A gross of 110,000 before fees.

    • Andy Rachleff August 28, 2014 at 5:12 pm #

      Your cost basis is $1.87/share for Regular Tax purposes and $4.47/share for AMT purposes. You must complete a separate IRS Schedule D for both calculations and include both Schedule Ds with the tax return you file with the IRS (the Schedule D for AMT purposes should state “ALTERNATIVE MINIMUM TAX” on the top of the form, which should be automatic with the tax preparation software you use).

      The difference in the net capital gain on the Schedule Ds is shown as a negative amount on Form 6251, Line 17 . This negative adjustment will reduce the 2014 AMT & should (largely) offset the AMT previously paid on shares sold (other tax items factor into Regular Tax & AMT calculations, so the reduction in 2014 AMT may not equal AMT paid in prior years).

      You should also check your 2012 & 2013 Federal Tax Returns to see if a Form 8801 was completed, in which case there may be an AMT credit carryover that can be used in 2014 (or succeeding years if not completely used in 2014). Your tax preparation software should carry this credit forward automatically.

      The AMT credit is typically pretty small since the stock basis adjustment for AMT purposes generally reduces AMT in year of sale to offset AMT paid in exercise year.

      As with all tax related issues, we strongly encourage you to seek the advice of a tax professional before taking any action.

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