When to Exercise Stock Options?

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The are 3 primary reasons when to exercise your employee stock options; Expiration is Imminent, Exercising Early, and Reducing Taxes.

It is a difficult question...

ESO is here to help.

Exercising employee stock options is like buying stock in a company for a discounted price. With this mindset, it only makes sense to exercise if you think the company will succeed. In a private company this means you believe the company will exit at some point either via an Initial Public Offering (IPO) or a Merger/Acquisition (M&A). In a public company this simply means you have confidence in the future of the company.

3 Reasons to Exercise Your Employee Stock Options:

  1. Expiration is Imminent
  2. Exercising Early
  3. Reducing Taxes

Below we will dive deeper into each of these reasons to exercise your stock options.

1. Expiration is Imminent

This is simple: if you have confidence in the company, it is almost always better to exercise than let your hard-earned options drop off the table for nothing. If you have already left the company, then you need to know how long you have before your options expire. For ISOs it is 90 days from your termination date, otherwise the company decides as NSOs can be extended well beyond the 90 day timeframe. In this case your incentive to exercise is clear: to prevent the options from expiring and losing ALL value. If you haven't left the company, but either plan to leave or want the flexibility to look around (or fear you may lose your job) it can be appealing to exercise because it will lower the stress once you do leave.

Often called "golden handcuffs," stock options are a great form of compensation, but can make employees feel stuck at their job due to high exercise costs. One way to unlock your golden handcuffs is to have someone else cover the option exercise for you. If you can't afford to take this risk on your expiring stock options, a non-recourse financing with ESO Fund allows you to keep your money in the short term, while maintaining the long-term upside potential of your options, all without taking on any personal risk. Another alternative would be asking the company for an NSO extension.

2. Exercising Early

For some, but not all, companies, an early exercise of un-vested options is available to employees. In many cases it can be advantageous to exercise your stock options early (provided you have the cash, and assuming you believe in the company given you accepted a job there). The first benefit of exercising early is that you will likely have zero (or very little) tax liability at the time of exercise. The second is that you will get a head start on the clock on long-term capital gains for options that you haven't even vested. Additionally, the lower long-term capital gains rate will be applied to all (or most) of your gains on the stock, rather than paying income tax (for NSOs) or AMT (for ISOs) on some phantom gains if you were to exercise once your options vested.

The most important thing to understand when considering this is what happens if you never vest options that were exercised early. This will likely be outlined in either your Stock Option Grant or Plan (or both). The vast majority of companies will simply repurchase any un-vested shares at cost (strike price). This means you won't stand to lose any money, but the opportunity cost of exercising options and tying up cash for no gain a number of years later isn't exactly ideal. A good rule of thumb for early exercise is to exercise as many options as you are confident you will vest based on how long you plan to stay with the company, worst case you stay longer and have to exercise a portion the normal way. You should look to file an 83(b) election with the IRS within 30 days of the exercise in order to prevent taxes being owed upon vesting.

3. Reducing Taxes

There are a number of ways to reduce stock option taxes, and reducing tax impact is a common motivation when exercising stock options.

a. Long-Term Capital Gains

If you have high confidence in the future of the company, you can exercise early to trigger taxes on long term capital gains. It may seem appealing to wait until the last-minute to exercise your options so you don't have to risk your own hard-earned cash up front. While this may be true, it fails to factor in that you pay taxes based on the spread between your strike price and the current Fair Market Value of the stock. If you wait, by the time you exercise, the tax implications may have gone up considerably. When considering this tactic, you should understand the implied tax savings. According to TurboTax, in 2017 short term capital gains taxation ranged from 10-39.5% and long-term capital gains is typically 0%, 15%, or 20%. If you are subject to AMT, the rate can be as high as 28%. You will need to weigh the savings of triggering long-term capital gains based on how much you think the price of the company will rise.

b. Exercising Before 409a Goes Up

Whether you will owe taxes on your exercise or not, if your company's valuation is about to rise significantly, it may make sense to exercise while your tax burden is still reasonable. Most of the time this situation will occur when the company is about to raise a large up-round of Venture Capital money. If the funding causes the price of the company to go up by a large multiple it could leave you hanging with a massive tax bill. Two recent examples of this were in the spring of 2019 when both JUUL and DoorDash were planning to raise massive up rounds from SoftBank. In both cases, the price of common stock ended up rising to more than 3 times the price prior to funding.

Here's an example:

Imagine you have 20,000 options vested with a strike price of $1. The current FMV is at $5 per share. Your exercise would cost $20,000 and you would owe taxes on $80,000 of gain. Let's estimate this using a 40% tax rate just to make the math easy. This means you would owe $32,000 in taxes for your exercise, bringing the total exercise cost to $52,000. Certainly not cheap, but reasonable.

Now let's say your company raises money and the FMV goes up to $21 per share. You now owe taxes on $400,000 of taxable gain. Using that same 40% rate means you would owe $160,000 in taxes for your exercise, bringing the total exercise cost to $180,000. More than 3 times the money you owed before the fundraising. In this example, had you exercised before the fundraising, you would have saved yourself $100,000. This example doesn't happen to every company, however there have certainly been more drastic changes than the one outlined above. One thing to consider is that just because your taxes may go up, it doesn't mean you NEED to exercise. You should still make sure it is a risk you can afford to take, and that you have confidence in the company. Looking back to DoorDash and JUUL, at the time it seemed like a no-brainer to lock in a low tax basis before they skyrocketed in value, however you can see that there are two sides of the coin. As of writing this, DoorDash is prepping for an IPO at a much higher valuation than that 2019 funding round, while JUUL has marked down their stock multiple times in the past year.

In this sort of scenario, it often makes sense to work with ESO Fund to cover the cost of the exercise to take advantage of the low tax liability.

c. Exercising ISOs Without AMT

The AMT exemption level in 2020 is $72,900 for individuals and $113,400 for married filing jointly. If you have vested ISOs with taxable gain below the exemption amount, you can exercise them without having to pay any taxes. Remember, the taxable gain calculation is Total Options * (409a Price - Strike Price). This can be very advantageous if your company is earlier stage and primed for explosive growth in value or if you are likely to leave before an exit event. It makes less sense if an exit is imminent, but is still a reasonable route to consider (i.e. you don't plan to leave anytime soon and can simply wait until post liquidity to exercise). Read more on exercising just enough ISOs each year to avoid AMT.

You can check out ESO's AMT Calculator to determine your AMT liability.

d. Qualified Small Business Stock

If you purchase your stock directly from a C corporation with less than $50 million in capitalization and hold for 5-years or longer you will qualify for Qualified Small Business Stock exemptions. Read more on QSBS.

Okay, the Time is Right to Exercise Your Options: Now What?

Once you decide it makes sense to exercise your stock options, here are three steps you need to take prior to exercising:

Step 1: Do you believe this is a good investment?

This means 1) do you think the company will be successful in exiting through an IPO or an M&A? and 2) do you think that the value of the common stock will increase higher than your strike price? Just because you worked there and have the right to exercise options doesn't necessarily mean you are not better off simply buying an S&P500 fund or shares of a publicly traded company. Keep in mind that even following an IPO, you typically must wait out a 6 month lockup period on the public markets, and the stock could go up or down during that period. If your company is large enough, they may be required to provide Rule 701 Disclosures to option holders. These disclosures include financial information that can help you make an informed decision on whether or not to exercise the options.

If you believe in the future of the company, proceed to step 2.

Step 2: How much will the exercise cost you (taxes included)?

The cost of the exercise itself is simple: the total number of options you plan to exercise time the strike price. For example exercising 10,000 options with an exercise price of $4 will cost you $40,000.

How much you owe in stock option taxes will depend on whether you have ISOs or NSOs. For Incentive Stock Options (ISOs) you will pay AMT Tax when you file taxes in April of the following year (here is some info on How to Calculate AMT Tax). For Non-Qualified Stock Options (NSOs or NQSOs) you will pay income tax that will be withheld by the company at the time of exercise. If you have an equity portal like Carta you may find your NSO tax number there, but often times you must reach out to someone at the company to confirm your tax liability.

In either case, your taxable gain is based on the current 409a value or Fair Market Value of the company's common stock. Take that number minus your strike price and multiplied by your number of options to find out how much taxable income will result from your exercise.

Once you have figured out the cost of the exercise, proceed to step 3.

Step 3: How do I plan to pay for this exercise?

The main question is "How much can I afford to exercise?" There are two definitions of "afford" to consider. 1) Do I physically have enough money to pay for this exercise and the associated taxes? and if the answer is yes, 2) Can I afford to risk the money required to exercise? Exercising private company shares always leaves the possibility of losing your entire investment on the table. Ideally, since you are confident in the company and have done as much research as you can, you have minimized the chance of losing your money. but it still exists (COVID-19 has shown that even in the best of times, things can change dramatically). If you can afford to exercise the whole grant, great! Exercise away! If not, looking into options like the ESO Fund to cover the cost of the exercise can be a great option. NOTE: even if you can afford to exercise 100% of your options, it still may be advantageous to work with ESO for free leverage and diversification.

In summary, a stock option exercise at a startup can be a great creator of wealth, but it does not come without any risks. It is important to understand when and if it makes sense to exercise.

For more information on how to monetize your private company equity, please contact us at the Employee Stock Option Fund.

This innovative service promotes and enables a healthier relationship between companies and employees. I my opinion it's valuable to employees and great for the overall tech environment and economy. It is good for nobody when employees feel trapped because they can't afford to leave. In less extreme cases exercising can be expensive and somewhat risky and this is simply a good smart hedge and a good square deal. Brilliant!

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