Before you accept a startup stock option offer, you will want to have a strategy in place for exercising the options. This will save you from the unhappy surprises associated with stock options, such as forfeiting vested options, golden handcuffs, or unnecessary tax expenses. There’s not a one-size-fits-all strategy, but there is a menu of choices, as this article presents.
- Strategy #1: Exercise At Liquidity
- Strategy #2: Forfeit Vested Options By Not Exercising
- Strategy #3: Exercise At Expiration, Before Liquidity
- Strategy #4: Early Exercise (Prior To Vesting)
- Strategy #5: Regularly Exercise Options As They Vest
Strategy #1: Exercise At Liquidity
The default for most startup employees is to wait to exercise their stock options until the company is acquired or they can sell the shares (such as after an IPO). They simply exercise the options and sell the shares on the same day.
The benefit of this default is that they have no out-of-pocket expense to exercise or pay taxes on the option exercise until they are certain they will have a market to sell those shares. It’s a no-risk choice from that perspective.
One downside of this strategy is that a same-day exercise and sale would tax your gains at ordinary income tax rates. Another downside of this strategy is a lack of career mobility. At most companies, options expire within three months of termination of employment. If you are waiting on an exit event to exercise your options, you may be stuck at the company until that exit event occurs.
Should you leave the company voluntarily or be terminated by the company before an exit event, you may be forced into exercising your options prior to liquidity or forfeiting the options when they expire. In addition, options have a final expiration date, usually 10 years from the date of grant. This seems like a long time, but occasionally companies do not have an exit event in this timeframe. This forces the employee to exercise prior to liquidity or forfeit the options when they expire.
One variation of this strategy is to negotiate during the hiring process for an extended post-termination exercise period for the options. If you have, for instance, the full 10-year term of the option to exercise regardless of your termination date, you can use this strategy and still be free to leave the company without forfeiting your options.
Return to table of contentsStrategy #2: Forfeit Vested Options By Not Exercising
Most startup employees do not exercise their options if they leave the company before an exit event because they do not want to invest money into the exercise price and tax cost and risk losing that investment. Therefore, forfeiture is probably the second most common option exercise choice for startup employees. Why?
All options have a final expiration date, which is usually 10 years from the date of grant. Most options also expire earlier upon any termination of employment. The standard is that employees have three months after termination of employment to exercise their options. An expiration date is a forfeiture date. If you do not exercise your option before it expires, it is forfeited, and you can never purchase the shares underlying the option.
A private company employee facing an expiring option has to make their investment in the shares before there is a public market for those shares. I call this the $1M problem because I regularly get calls from startup optionholders who need to come up with $1M to exercise their options and pay the tax cost of exercise. The exercise price of an option may be quite high in itself, especially for an employee who joins later in the startup’s growth. It is the tax cost of exercising, though, that prevents most startup employees from exercising their options.
Strategy #3: Exercise At Expiration, Before Liquidity
Not all startup employees forfeit their options if they leave the company before a liquidity event. Many make the investment to pay the exercise price and the associated tax cost when they leave the company so they can acquire the shares they worked to vest.
The exercise of an option is a taxable event, so the optionholder recognizes taxable income based on the difference between the exercise price and the FMV on the date of exercise. That might be taxed as AMT for ISOs or as ordinary income for NQSOs. Either way, it can result in tax bills in the millions of dollars for the exercise of a valuable option.
The tax on an option exercise is due whether or not there is a market to sell the shares to cover the tax bill. Some people call this “phantom income” or a “dry tax charge,” but it’s very real. I’ve heard horror stories about people losing their homes (and moving in with their in-laws) because they exercised their options and incurred this tax expense but did not have a market to sell the shares.
In some cases, those shares later were cashed out at a high value in a company exit event, which in the end made the risk of paying the exercise price and tax bill a very wise choice. Sometimes, though, the investment of the exercise price and the tax bill is lost, since the shares can end up either being worth less than the exercise price or worth less than the taxable value of the shares at exercise.
To avoid this scenario, some startup hires negotiate during the hiring process for an extended post-termination exercise period for the options. This allows them to follow Strategy #1 above (exercise at liquidity) and also have career mobility to leave the company before an exit event and still take advantage of their options.
Strategy #4: Early Exercise (Prior To Vesting)
An “early exercise” is an exercise of unvested stock options. You pay the exercise price to the company and file an 83(b) election with the IRS within 30 days of exercise. The shares are still subject to vesting, as the unvested shares can be repurchased from you if you leave the company prior to your vesting dates.
Early exercise is a popular tax-planning maneuver, as it starts your holding period for capital gains and, perhaps, Qualified Small Business Stock (QSBS). This sets you up for the lowest possible tax rates when you sell your shares. It may also help you avoid the tax cost of exercise. If you make an early exercise immediately after grant, while your exercise price is still equal to the FMV of the shares, you have a $0 tax cost to exercise.
Early exercise is not available at every company, but it is worth considering if it is available to you. It may also make sense to negotiate for the right to make an early exercise as part of your offer negotiation if it is not offered to you, as I explain in my video about negotiating early-stage equity offers. I have also had clients who ask for this right to be added to their options well after they join the company, especially if the company valuation is about to explode and they want to exercise unvested shares before the tax cost would make any exercise impossible.
The downside of early exercise is investment risk, as you have to pay the exercise price (and, perhaps, some taxes at exercise) out of pocket before you have any visibility into whether the value of the shares will go up. Early exercise is very common and an easy choice at early stage companies where the FMV and, therefore, the exercise price is low. It’s a less obvious choice when the company is at a later stage and the exercise price of stock options is significant. (See also my video on exercise-price basics in startups.)
Strategy #5: Regularly Exercise Options As They Vest
The final strategy is to exercise options regularly as they vest. This is the least popular but (in many cases) the most favorable strategy.
It’s unpopular because it requires both attention and money, which are both in high demand for startup employees. It’s favorable because it provides for some of the same benefits of early exercise: it starts your tax holding period and allows you to avoid the golden handcuffs that come with unexercised options as the tax cost to exercise increases over time.
The downside of this strategy is, of course, the investment risk of paying the exercise price and tax cost of exercise. There is no guarantee that startup stock will ever become more valuable than your exercise price, or that you will be made whole for the taxes paid to exercise.
How does it work? First, you would need to stay apprised of the current FMV of the company’s common stock and upcoming corporate events that might increase its FMV. Since the FMV of the common shares on the date of your exercise will determine the tax cost to exercise, you will need to know this to make a thoughtful exercise decision.
Second, you would regularly consider whether or not to exercise your vested options. Most people approach this by meeting with their tax or financial advisor on a regular basis to calculate the expense of exercising their vested stock options. This would be done annually (or even more frequently if the company is anticipating an event that would increase its FMV). If you have ISOs, this would include an analysis of how many options you can exercise tax-free by staying under the AMT exemption amount. If you have ISOs or NQSOs, it would include an analysis of the total tax cost to exercise as well as the financial costs/benefits of exercising.
Finally, you would pay the exercise price and associated tax cost (if any) to exercise the vested options.
Think Through The Choices
I hope this article inspires you to choose a strategy before you accept a stock option offer from a startup. It’s worth the time and attention to understand your choices and come up with a thoughtful plan of action before you invest years of your time to earn startup stock options.
Attorney Mary Russell (Stock Option Counsel, P.C.) counsels individuals on equity grants, executive compensation design, employment agreements, and acquisition terms. This article was published solely for its content and quality. Neither the author nor her firm compensated us in exchange for publication of this article.
