Worker Stock Options (ESOs): A Complete Guide

What Is an Worker Stock Option (ESO)?

The term worker stock option (ESO) refers to a kind of equity compensation granted by corporations to their employees and executives. Moderately than granting shares of stock directly, the corporate gives derivative options on the stock as a substitute. These options are available in the shape of standard call options and provides the worker the fitting to purchase the corporate’s stock at a specified price for a finite time period. Terms of ESOs will probably be fully spelled out for an worker in an worker stock options agreement.

On the whole, the best advantages of a stock option are realized if an organization’s stock rises above the exercise price. Typically, ESOs are issued by the corporate and can’t be sold, unlike standard listed or exchange-traded options. When a stock’s price rises above the decision option exercise price, call options are exercised and the holder obtains the corporate’s stock at a reduction. The holder may select to right away sell the stock within the open marketplace for a profit or hold onto the stock over time.

Key Takeaways

  • Worker stock options are offered by corporations to their employees as equity compensation plans.
  • These grants are available in the shape of standard call options and provides an worker the fitting to purchase the corporate’s stock at a specified price for a finite time period.
  • ESOs can have vesting schedules that limit the flexibility to exercise.
  • ESOs are taxed at exercise and stockholders will probably be taxed in the event that they sell their shares within the open market.
  • They will have significant time value even in the event that they have zero or little intrinsic value.

Understanding Worker Stock Options (ESOs)

Corporate advantages for some or all employees may include equity compensation plans. These plans are known for providing financial compensation in the shape of stock equity. ESOs are only one kind of equity compensation an organization may offer. Other sorts of equity compensation may include:

  1. Restricted Stock Grants: these give employees the fitting to accumulate or receive shares once certain criteria are attained, like working for an outlined variety of years or meeting performance targets.
  2. Stock Appreciation Rights (SARs): SARs provide the fitting to the rise in the worth of a delegated variety of shares; such a rise in value is payable in money or company stock.
  3. Phantom Stock: this pays a future money bonus equal to the worth of an outlined variety of shares; no legal transfer of share ownership normally takes place, although the phantom stock could also be convertible to actual shares if defined trigger events occur.
  4. Worker Stock Purchase Plans: these plans give employees the fitting to buy company shares, normally at a reduction.

In broad terms, the commonality between all these equity compensation plans is that they offer employees and stakeholders an equity incentive to construct the corporate and share in its growth and success.

For workers, the important thing advantages of any kind of equity compensation plan are:

  • A chance to share directly in the corporate’s success through stock holdings
  • Pride of ownership; employees may feel motivated to be fully productive because they own a stake in the corporate
  • Provides a tangible representation of how much their contribution is price to the employer
  • Depending on the plan, it might offer the potential for tax savings upon sale or disposal of the shares

The advantages of an equity compensation plan to employers are:

  • It’s a key tool to recruit the most effective and the brightest in an increasingly integrated global economy where there may be worldwide competition for top talent
  • Boosts worker job satisfaction and financial wellbeing by providing lucrative financial incentives
  • Incentivizes employees to assist the corporate grow and succeed because they’ll share in its success
  • Could also be used as a possible exit strategy for owners, in some instances

There are two essential sorts of ESO:

  1. Incentive stock options (ISOs), also referred to as statutory or qualified options, are generally only offered to key employees and top management. They receive preferential tax treatment in lots of cases, because the IRS treats gains on such options as long-term capital gains.
  2. Non-qualified stock options (NSOs) may be granted to employees in any respect levels of an organization, in addition to to board members and consultants. Also referred to as non-statutory stock options, profits on these are considered abnormal income and are taxed as such.

Stock options are a profit often related to startup corporations, which can issue them so as to reward early employees when and if the corporate goes public. They’re awarded by some fast-growing corporations as an incentive for workers to work towards growing the worth of the corporate’s shares. Stock options may also function an incentive for workers to stick with the corporate. The choices are canceled if the worker leaves the corporate before they vest. ESOs don’t include any dividend or voting rights.

Essential Concepts

There are two key parties within the ESO, the grantee (worker) and grantor (employer). The grantee—also referred to as the optionee—may be an executive or an worker, while the grantor is the corporate that employs the grantee. The grantee is given equity compensation in the shape of ESOs, normally with certain restrictions, probably the most essential of which is the vesting period.

The vesting period is the length of time that an worker must wait so as to find a way to exercise their ESOs. Why does the worker must wait? Since it gives the worker an incentive to perform well and stick with the corporate. Vesting follows a pre-determined schedule that is ready up by the corporate on the time of the choice grant.


ESOs are considered vested when the worker is allowed to exercise the choices and buy the corporate’s stock. Note that the stock is probably not fully vested when purchased with an option in certain cases, despite exercising the stock options, as the corporate may not wish to run the chance of employees making a fast gain (by exercising their options and immediately selling their shares) and subsequently leaving the corporate. 

If you have got received an options grant, you need to rigorously undergo your organization’s stock options plan, in addition to the choices agreement, to find out the rights available and restrictions applied to employees. The stock options plan is drafted by the corporate’s board of directors and accommodates details of the grantee’s rights. The choices agreement will provide the important thing details of your option grant comparable to the vesting schedule, how the ESOs will vest, shares represented by the grant, and the strike price.

In case you are a key worker or executive, it might be possible to barter certain facets of the choices agreement, comparable to a vesting schedule where the shares vest faster, or a lower exercise price. It may be worthwhile to debate the choices agreement together with your financial planner or wealth manager before you sign on the dotted line.

ESOs typically vest in chunks over time at predetermined dates, as set out within the vesting schedule. For instance, chances are you’ll be granted the fitting to purchase 1,000 shares, with the choices vesting 25% per yr over 4 years with a term of 10 years. So 25% of the ESOs, conferring the fitting to purchase 250 shares would vest in a single yr from the choice grant date, one other 25% would vest two years from the grant date, and so forth.

In case you don’t exercise your 25% vested ESOs after yr one, you’ll have a cumulative increase in exercisable options. Thus, after yr two, you’ll now have 50% vested ESOs. In case you don’t exercise any of ESOs options in the primary 4 years, you’ll have 100% of the ESOs vested after that period, which you’ll then exercise in full or partly. As mentioned earlier, we had assumed that the ESOs have a term of 10 years. Because of this after 10 years, you’ll not have the fitting to purchase shares. Due to this fact, the ESOs have to be exercised before the 10-year period (counting from the date of the choice grant) is up.

Receiving Stock

Continuing with the above example, let’s say you exercise 25% of the ESOs after they vest after one yr. This implies you’ll get 250 shares of the corporate’s stock on the strike price. It ought to be emphasized that the record price for the shares is the exercise price or strike price laid out in the choices agreement, regardless of the particular market price of the stock.

Reload Option

In some ESO agreements, an organization may offer a reload option. A reload option is a pleasant provision to make the most of. With a reload option, an worker may be granted more ESOs after they exercise currently available ESOs.

ESOs and Taxation

We now arrive on the ESO spread. As will probably be seen later, this triggers a tax event whereby abnormal income tax is applied to the spread.

The next points have to be borne in mind with regard to ESO taxation:

  • The choice grant itself will not be a taxable event. The grantee or optionee will not be faced with a direct tax liability when the choices are granted by the corporate. Note that typically (but not all the time), the exercise price of the ESOs is ready on the market price of the corporate’s stock on the day of the choice grant.
  • Taxation begins on the time of exercise. The spread (between the exercise price and the market price) can be referred to as the bargain element in tax parlance, and is taxed at abnormal income tax rates since the IRS considers it as a part of the worker’s compensation.
  • The sale of the acquired stock triggers one other taxable event. If the worker sells the acquired shares for lower than or up to 1 yr after exercise, the transaction can be treated as a short-term capital gain and can be taxed at abnormal income tax rates. If the acquired shares are sold multiple yr after exercise, it will qualify for the lower capital gains tax rate.

Let’s display this with an example. Let’s say you have got ESOs with an exercise price of $25, and with the market price of the stock at $55, want to exercise 25% of the 1,000 shares granted to you as per your ESOs.

The record price can be $6,250 for the shares ($25 x 250 shares). For the reason that market value of the shares is $13,750, if you happen to promptly sell the acquired shares, you’ll net pre-tax earnings of $7,500. This spread is taxed as abnormal income in your hands within the yr of exercise, even if you happen to don’t sell the shares. This feature can create a big tax liability if you happen to proceed to carry the stock and it plummets in value because of the exercise.

Let’s recap a crucial point—why are you taxed on the time of ESO exercise? The flexibility to purchase shares at a big discount to the present market price (a bargain price, in other words) is viewed by the IRS as a part of the overall compensation package provided to you by your employer, and is subsequently taxed at your income tax rate. Thus, even if you happen to don’t sell the shares acquired pursuant to your ESO exercise, you trigger a tax liability on the time of exercise.

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Intrinsic Value vs. Time Value for ESOs

The worth of an option consists of intrinsic value and time value (extrinsic value). Time value depends upon the period of time remaining until expiration (the date when the ESOs expire) and a number of other other variables. Given that the majority ESOs have a stated expiration date of as much as 10 years from the date of option grant, their time value may be quite significant. While time value may be easily calculated for exchange-traded options, it is more difficult to calculate time value for non-traded options like ESOs, since a market price will not be available for them.

To calculate the time value to your ESOs, you would need to use a theoretical pricing model just like the well-known Black-Scholes option pricing model to compute the fair value of your ESOs. You will want to plug inputs comparable to the exercise price, time remaining, stock price, risk-free rate of interest, and volatility into the Model so as to get an estimate of the fair value of the ESO. From there, it is a straightforward exercise to calculate time value, as may be seen below. Do not forget that intrinsic value—which might never be negative—is zero when an option is “at the cash” (ATM) or “out of the cash” (OTM); for these options, their entire value subsequently consists only of time value.

The exercise of an ESO will capture intrinsic value but normally gives up time value (assuming there may be any left), leading to a potentially large hidden opportunity cost. Assume that the calculated fair value of your ESOs is $40, as shown below. Subtracting intrinsic value of $30 gives your ESOs a time value of $10. In case you exercise your ESOs in this example, you can be giving up time value of $10 per share, or a complete of $2,500 based on 250 shares.

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The worth of your ESOs will not be static, but will fluctuate over time based on movements in key inputs comparable to the worth of the underlying stock, time to expiration, and above all, volatility. Consider a situation where your ESOs are out of the cash (i.e., the market price of the stock is now below the ESOs exercise price).

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It could be illogical to exercise your ESOs on this scenario for 2 reasons. Firstly, it’s cheaper to purchase the stock within the open market at $20, compared with the exercise price of $25. Secondly, by exercising your ESOs, you can be relinquishing $15 of time value per share. In case you think the stock has bottomed out and need to accumulate it, it will be far more preferable to easily buy it at $25 and retain your ESOs, providing you with larger upside potential (with some additional risk, because you now own the shares as well).

ESOs vs. Listed Options

The most important and most evident difference between ESOs and listed options is that ESOs usually are not traded on an exchange, and hence wouldn’t have the numerous advantages of exchange-traded options.

The Value of Your ESO Is Not Easy to Ascertain

Exchange-traded options, especially on the most important stock, have an ideal deal of liquidity and trade steadily, so it is simple to estimate the worth of an options portfolio. Not so together with your ESOs, whose value will not be as easy to establish, because there is no such thing as a market price reference point. Many ESOs are granted with a term of 10 or more years, but there are virtually no listed options that trade for that length of time. LEAPs (long-term equity anticipation securities) are among the many longest-dated options available, but even they only go three years out, which might only help in case your ESOs have three years or less to expiration.

Option pricing models are subsequently crucial so that you can know the worth of your ESOs. Your employer is required—on the choices grant date—to specify a theoretical price of your ESOs in your options agreement. You’ll want to request this information from your organization, and in addition learn how the worth of your ESOs has been determined.

Option prices can vary widely, depending on the assumptions made within the input variables. For instance, your employer may ensure assumptions concerning the expected length of employment and estimated holding period before exercise, which could shorten the time to expiration. With listed options, however, the time to expiration is specified and can’t be arbitrarily modified. Assumptions about volatility may also have a big impact on option prices. If your organization assumes lower than normal levels of volatility, your ESOs can be priced lower. It could be a great idea to get several estimates from other models to match them together with your company’s valuation of your ESOs.

Specifications Are Not Standardized

Listed options have standardized contract terms with regard to the variety of shares underlying an options contract, expiration date, etc. This uniformity makes it easy to trade options on any optionable stock, whether it’s Apple or Google or Qualcomm. In case you trade a call option contract, as an example, you have got the fitting to purchase 199 shares of the underlying stock at the required strike price until expiration.

Similarly, a put option contract gives you the fitting to sell 100 shares of the underlying stock until expiration. While ESOs do have similar rights to listed options, the fitting to purchase shares will not be standardized and is spelled out in the choices agreement.

No Automatic Exercise

For all listed options within the U.S., the last day of trading is the third Friday of the calendar month of the choice contract. If the third Friday happens to fall on an exchange holiday, the expiration date moves up by a day to that Thursday. On the close of trading on the third Friday, the choices related to that month’s contract stop trading and are robotically exercised in the event that they are greater than $0.01 (1 cent) or more in the cash. Thus, if you happen to owned one call option contract and at expiration, the market price of the underlying stock was higher than the strike price by one cent or more, you’ll own 100 shares through the automated exercise feature.

Likewise, if you happen to owned a put option and at expiration, the market price of the underlying stock was lower than the strike price by one cent or more, you can be short 100 shares through the automated exercise feature. Note that despite the term “automatic exercise,” you continue to have control over the eventual final result, by providing alternate instructions to your broker that take precedence over any automatic exercise procedures, or by closing out the position prior to expiration. With ESOs, the precise details about after they expire may differ from one company to the subsequent. Also, as there is no such thing as a automatic exercise feature with ESOs, you have got to notify your employer if you happen to want to exercise your options.

Strike Prices

Listed options have standardized strike prices (exercise prices), coming in increments comparable to $1, $2.50, $5, or $10, depending on the worth of the underlying security (higher-priced stocks have wider increments). With ESOs, because the strike price is often the stock’s closing price on a selected day, there aren’t any standardized strike prices.

Within the mid-2000s, an ESO backdating scandal within the U.S. resulted within the resignations of many executives at top firms. This practice involved granting an option at a previous date as a substitute of the present date, thus setting the strike price at a lower cost than the market price on the grant date and giving an quick gain to the choice holder. ESO backdating has turn out to be far more difficult because the introduction of Sarbanes-Oxley as corporations are actually required to report option grants to the SEC inside two business days.

Vesting and Acquired Stock Restrictions

Vesting gives rise to manage issues that usually are not present in listed options. ESOs may require the worker to realize a level of seniority or meet certain performance targets before they vest. If the vesting criteria usually are not crystal clear, it might create a murky legal situation, especially if relations sour between the worker and employer. As well, with listed options, when you exercise your calls and acquire the stock you’ll be able to get rid of it as soon as you would like with none restrictions. Nonetheless, with acquired stock through an exercise of ESOs, there could also be restrictions that prevent you from selling the stock.

Even in case your ESOs have vested and you’ll be able to exercise them, the acquired stock is probably not vested. This could pose a dilemma, since you could have already paid tax on the ESO Spread (as discussed earlier) and now hold a stock that you just cannot sell (or that’s declining). 

Counterparty Risk

As scores of employees discovered within the aftermath of the Nineteen Nineties dot-com bust when quite a few technology corporations went bankrupt, counterparty risk is a legitimate issue that’s hardly considered by those that receive ESOs. With listed options within the U.S, the Options Clearing Corporation serves because the clearinghouse for options contracts and guarantees their performance.

Thus, there may be zero risk that the counterparty to your options trade will probably be unable to satisfy the obligations imposed by the choices contract. But because the counterparty to your ESOs is your organization, with no intermediary in between, it will be prudent to observe its financial situation to be certain that you usually are not left holding valueless unexercised options, and even worse, worthless acquired stock.

Concentration Risk

You possibly can assemble a diversified options portfolio using listed options but with ESOs, you have got concentration risk, since all of your options have the identical underlying stock. Along with your ESOs, if you happen to even have a big amount of company stock in your worker stock ownership plan (ESOP), chances are you’ll unwittingly have an excessive amount of exposure to your organization, a concentration risk that has been highlighted by FINRA.

Valuation and Pricing Issues

The essential determinants of an option’s value are volatility, time to expiration, the risk-free rate of interest, strike price, and the underlying stock’s price. Understanding the interplay of those variables–especially volatility and time to expiration–is crucial for making informed decisions concerning the value of your ESOs.

In the next example, we assume an ESO grants the fitting (when vested) to purchase 1,000 shares of the corporate at a strike price of $50, which is the stock’s closing price on the day of the choice grant (making this an at-the-money option upon grant). The primary table below uses the Black-Scholes option pricing model to isolate the impact of time decay while keeping volatility constant, while the second illustrates the impact of upper volatility on option prices.

As may be seen, the greater the time to expiration, the more the choice is price. Since we assume that is an at-the-money option, its entire value consists of time value. The primary table demonstrates two fundamental options pricing principles:

  1. Time value is an important component of options pricing. In case you are awarded at-the-money ESOs with a term of 10 years, their intrinsic value is zero, but they’ve a considerable period of time value, $23.08 per option on this case, or over $23,000 for ESOs that offer you the fitting to purchase 1,000 shares.
  2. Option time decay will not be linear in nature. The worth of options declines because the expiration date approaches, a phenomenon referred to as time decay, but this time decay will not be linear in nature and accelerates near option expiry. An option that is much out-of-the-money will decay faster than an option that’s at the cash since the probability of the previous being profitable is way lower than that of the latter.

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The table below shows option prices based on the identical assumptions, except that volatility is assumed to be 60% reasonably than 30%. This increase in volatility has a big effect on option prices. For instance, with 10 years remaining to expiration, the worth of the ESO increases 53% to $35.34, while with two years remaining, the worth increases 80% to $17.45. Further on shows option prices in graphical form for a similar time remaining to expiration, at 30% and 60% volatility levels.

Similar results are obtained by changing the variables to levels that prevail at present. With volatility at 10% and the risk-free rate of interest at 2%, the ESOs can be priced at $11.36, $7.04, $5.01, and $3.86 with time to expiration at 10, five, three, and two years respectively.

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The important thing takeaway from this section is that merely because your ESOs haven’t any intrinsic value, don’t make the naïve assumption that they’re worthless. Due to their very long time to expiration in comparison with listed options, ESOs have a big period of time value that shouldn’t be frittered away through early exercise.

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Risk and Reward Associated With Owning ESOs

As discussed within the preceding section, your ESOs can have significant time value even in the event that they have zero or little intrinsic value. On this section, we use the common 10-year grant term to expiration to display the chance and reward related to owning ESOs.

If you receive the ESOs on the time of grant, you usually haven’t any intrinsic value since the ESO strike price or exercise price is the same as the stock’s closing price on that day. As your exercise price and the stock price are the identical, that is an at-the-money option. Once the stock begins to rise, the choice has intrinsic value, which is intuitive to grasp and simple to compute. But a standard mistake will not be realizing the importance of time value, even on the grant day, and the chance cost of premature or early exercise.

Actually, your ESOs have the very best time value at grant (assuming that volatility doesn’t spike soon after you acquire the choices). With such a big time value component—as demonstrated above—you truly have value that’s in danger.

Assuming you hold ESOs to purchase 1,000 shares at an exercise price of $50 (with volatility at 60% and 10 years to expiration), the potential lack of time value is sort of steep. If the shares are unchanged at $50 in 10 years time, you’ll lose $35,000 in time value and can be left with nothing to point out to your ESOs.

This lack of time value ought to be factored in when computing your eventual return. Let’s say the stock rises to $110 by expiration in 10 years time, providing you with an ESO spread—akin to intrinsic value—of $60 per share, or $60,000 in total. Nonetheless, this ought to be offset by the $35,000 loss in time value by holding the ESOs to expiration, leaving a net pre-tax “gain” of just $25,000. Unfortunately, this lack of time value will not be tax-deductible, which suggests that the abnormal income tax rate (assumed at 40%) can be applied to $60,000 (and never $25,000). Taking out $24,000 for compensation tax paid at exercise to your employer would depart you with $36,000 in after-tax income, but if you happen to deduct the $35,000 lost in time value, you can be left with just $1,000 in hand.

Holding ESOs Until Expiration

Before we take a look at a number of the issues surrounding early exercise—not holding ESOs until expiration—let’s evaluate the final result of holding ESOs until expiration in light of time value and tax costs. Below shows the after-tax, net of time value gains and losses at expiration. At a price of $120 upon expiration, actual gains (after subtracting time value) are only $7,000. That is calculated as a diffusion of $70 per share or $70,000 in total, less compensation tax of $28,000, leaving you with $42,000 from which you subtract $35,000 for time value lost, for a net gain of $7,000.

Note that whenever you exercise the ESOs, you would need to pay the exercise price plus tax even if you happen to don’t sell the stock (recall that exercise of ESOs is a tax event), which on this case equates to $50,000 plus $28,000, for a complete of $78,000. In case you immediately sell the stock on the prevailing price of $120, you receive proceeds of $120,000, from which you would need to subtract $78,000. The “gain” of $42,000 ought to be offset by the $35,000 decline in time value, leaving you with $7,000.

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Early or Premature Exercise

As a strategy to reduce risk and lock in gains, early or premature exercise of ESOs have to be rigorously considered, since there may be a big potential tax hit and massive opportunity cost in the shape of forfeited time value. On this section, we discuss the means of early exercise and explain financial objectives and risks.

When an ESO is granted, it has a hypothetical value that—since it is an at-the-money option—is pure time value. This time value decays at a rate referred to as theta, which is a square root function of the time remaining.

Assume you hold ESOs which are price $35,000 upon grant, as discussed in the sooner sections. You think within the long-term prospects of your organization and plan to carry your ESOs until expiration. Below shows the worth composition—intrinsic value plus time value—for ITM, ATM, and OTM options. 

Value Composition for In-, Out-, and At-the-Money ESO Option With Strike of $50 (Prices in $ 1000’s)

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Even if you happen to begin to achieve intrinsic value as the worth of the underlying stock rises, you will probably be shedding time value along the best way (although not proportionately). For instance, for an in-the-money ESO with a $50 exercise price and a stock price of $75, there will probably be less time value and more intrinsic value, for more value overall.

The out-of-the-money options (bottom set of bars) show only pure time value of $17,500, while the at-the-money options have time value of $35,000. The further out of the cash that an option is, the less time value it has, because the chances of it becoming profitable are increasingly slim. As an option gets more in the cash and acquires more intrinsic value, this forms a greater proportion of the overall option value. Actually, for a deeply in-the-money option, time value is an insignificant component of its value, compared with intrinsic value. When intrinsic value becomes value in danger, many option holders look to lock in all or a part of this gain, but in doing so, they not only quit time value but additionally incur a hefty tax bill.

Tax Liabilities for ESOs

We cannot emphasize this point enough—the most important downsides of premature exercise are the massive tax event it induces, and the lack of time value. You might be taxed at abnormal income tax rates on the ESO spread or intrinsic value gain, at rates as high as 40%. What’s more, it’s all due in the identical tax yr and paid upon exercise, with one other likely tax hit on the sale or disposition of the acquired stock. Even when you have got capital losses elsewhere in your portfolio, you’ll be able to only apply $3,000 per yr of those losses against your compensation gains to offset the tax liability.

After you have got acquired stock that presumably has appreciated in value, you might be faced with the selection of liquidating the stock or holding it. In case you sell immediately upon exercise, you have got locked in your compensation “gains” (the difference between the exercise price and stock market price).

But if you happen to hold the stock, after which sell it afterward after it appreciates, you could have more taxes to pay. Do not forget that the stock price on the day you exercised your ESOs is now your “basis price.” In case you sell the stock lower than a yr after exercise, you should have to pay short-term capital gains tax. To get the lower, long-term capital gains rate, you would need to hold the shares for greater than a yr. You thus find yourself paying two taxes—compensation and capital gains.

Many ESO holders may find themselves within the unlucky position of holding on to shares that reverse their initial gains after exercise, as the next example demonstrates. Let’s say you have got ESOs that offer you the fitting to purchase 1,000 shares at $50, and the stock is trading at $75 with five more years to expiration. As you might be anxious concerning the market outlook or the corporate’s prospects, you exercise your ESOs to lock within the spread of $25.

You now resolve to sell one-half of your holdings (of 1,000 shares) and keep the opposite half for potential future gains. Here’s how the maths stacks up:

  • Exercised at $75 and paid compensation tax on the total spread of $25 x 1,000 shares @ 40% = $10,000
  • Sold 500 shares at $75 for a gain of $12,500
  • Your after-tax gains at this point: $12,500 – $10,000 = $2,500
  • You are actually holding 500 shares with a basis price of $75, with $12,500 in unrealized gains (but already tax paid for)
  • Let’s assume the stock now declines to $50 before year-end
  • Your holding of 500 shares has now lost $25 per share or $12,500, because you acquired the shares through exercise (and already paid tax at $75)
  • In case you now sell these 500 shares at $50, you’ll be able to only apply $3,000 of those losses in the identical tax yr, with the remainder to be applied in future years with the identical limit

To summarize:

  • You paid $10,000 in compensation tax at exercise
  • Locked in $2,500 in after-tax gains on 500 shares
  • Broke even on 500 shares, but have losses of $12,500 you can write off per yr by $3,000

Note that this doesn’t count the time value lost from early exercise, which could possibly be quite significant with five years left for expiration. Having sold your holdings, you furthermore may not have the potential to achieve from an upward move within the stock. That said, while it seldom is sensible to exercise listed options early, the non-tradable nature and other limitations of ESOs may make their early exercise obligatory in the next situations:

  • Need for Cashflow: Oftentimes, the necessity for immediate cashflow may offset the chance cost of time value lost and justify the tax impact
  • Portfolio Diversification: As mentioned earlier, a very concentrated position in the corporate’s stock would necessitate early exercise and liquidation so as to achieve portfolio diversification
  • Stock or Market Outlook: Moderately than see all gains dissipate and switch into losses on account of a deteriorating outlook for the stock or equity market basically, it might be preferable to lock in gains through early exercise
  • Delivery for a Hedging Strategy: Writing calls to achieve premium income may require the delivery of stock (discussed in the subsequent section)

Basic Hedging Strategies for ESOs

Basic ESO hedging strategies include writing calls, buying puts, and constructing costless collars. Of those strategies, writing calls is the just one where the erosion of time value in ESOs may be offset by getting time decay working in a single’s favor. We strongly recommend that you just discuss any hedging strategies together with your financial planner or wealth manager. Also review your organization’s code of ethics and/or related policies—there could also be restricted practices on dealing in options related to your organization through which chances are you’ll be considered an insider.

We use options on the hypothetical XYZ Corp., to display hedging concepts. Say that XYZ closed at $175.13 on November 15, the date at which period the longest-dated options available on the stock are the three-year calls and puts.

Let’s assume you might be an XYZ worker who’s granted ESOs to purchase 500 shares of the corporate on Nov. 29, which is able to vest in 1/3 increments over the subsequent three years, and have 10 years to expiration. For reference, the three-year $175 calls available in the market are priced at $32.81 (ignoring bid-ask spreads for simplicity), while the 175 puts trade at $24.05.

Listed here are three basic hedging strategies, based in your assessment of the stock’s outlook. To maintain things easy, we assume that you just want to hedge the potential 500-share long position to simply past three years.

  1. Write Calls: The idea here is that you just are neutral to moderately bullish on XYZ, through which case one possibility to get time value decay working in your favor is by writing calls. While writing naked or uncovered calls is usually a very dangerous business, on this case your short call position can be covered by the five hundred shares you’ll be able to acquire through the exercise of the ESOs. You subsequently write five contracts (each contract covers 100 shares) with a strike price of $250, which might fetch you $10.55 in premium (per share), for a complete of $5,275 (excluding costs comparable to commission, margin interest etc.). If the stock goes sideways or trades lower over the subsequent three years, you pocket the premium, and repeat the strategy after three years. If the stock rockets higher and your XYZ shares are “called” away, you’ll still receive $250 per XYZ share, which together with the $10.55 premium, equates to a return of just about 50%. (Note that your shares are unlikely to be called away well before the three-year expiration because the choice buyer wouldn’t want to lose time value through early exercise). One other alternative is to write down one call contract one yr out, one other contract two years out, and three contracts three years out.
  2. Buy Puts: Let’s say that although you might be a loyal XYZ worker, you might be a tad bearish on its prospects. This strategy of shopping for puts will only provide you downside protection, but won’t resolve the time decay issue. You’re thinking that the stock could trade below $150 over the subsequent three years, and subsequently buy the three-year $150 puts which are available at $14.20. Your outlay on this case can be $7,100 for five contracts. You’ll break even when XYZ trades at $135.80 and would earn cash if the stock trades below that level. If the stock doesn’t decline below $150 inside three years’ time, you’ll lose the total $7,100, and if the stock trades between $135.80 and $150 by you then would recoup a part of the premium paid. This strategy wouldn’t require you to exercise your ESOs and may be pursued as a stand-alone strategy as well.
  3. Costless Collar: This strategy allows you to construct a collar that establishes a trading band to your XYZ holdings, at no or minimal upfront cost. It consists of a covered call, with part or the entire premium received used to purchase a put. On this case, writing the 3-year $215 calls will fetch $19.90 in premium, which may be used to purchase the 3-year $165 puts at $19.52. On this strategy, your stock runs the chance of being called away if it trades above $215, but your downside risk is capped at $165. 

Of those strategies, writing calls is the just one where you’ll be able to offset the erosion of time value in your ESOs by getting time decay working in your favor. Buying puts aggravates the problem of time decay but is a great technique to hedge downside risk, while the costless collar has minimal cost but doesn’t resolve the problem of ESO time decay.

How Do ESOs Differ From Listed Options?

ESOs differ from exchange-traded or listed options in some ways. As they usually are not traded, their value will not be easy to establish. Unlike listed options, ESOs wouldn’t have standardized specifications or automatic exercise. Counterparty risk and concentration risk are two risks of which ESO holders ought to be cognizant.

Are ESOs Worthless at First?

Although ESOs haven’t any intrinsic value at option grant, it will be naïve to assume that they’re worthless. Due to their lengthy time to expiration in comparison with listed options, ESOs have a big period of time value that shouldn’t be frittered away through early exercise.

What Are the Tax Implications of Receiving Worker Stock Options?

While the choice grant will not be a taxable event, taxation begins on the time of exercise and the sale of acquired stock also triggers one other taxable event. Tax payable on the time of exercise is a significant deterrent against early exercise of ESOs.

Despite the massive tax liability and lack of time value incurred through early exercise, it might be justified in certain cases, comparable to when cashflow is required, portfolio diversification is required, the stock or market outlook is deteriorating, or stock must be delivered for a hedging strategy using calls.

The Bottom Line

ESOs are a type of equity compensation granted by corporations to their employees and executives. Like a daily call option, an ESO gives the holder the fitting to buy the underlying asset—the corporate’s stock—at a specified price for a finite time period. ESOs usually are not the one type of equity compensation, but they’re amongst probably the most common.

Stock options are of two essential types. Incentive stock options, generally only offered to key employees and top management, receive preferential tax treatment in lots of cases, because the IRS treats gains on such options as long-term capital gains. Non-qualified stock options (NSOs) may be granted to employees in any respect levels of an organization, in addition to to board members and consultants. Also referred to as non-statutory stock options, profits on these are considered to be abnormal income and are taxed as such.

ESO holders ought to be acquainted with their company’s stock options plan in addition to their options agreement to grasp any restrictions and clauses therein. Employees must also be acquainted with their company’s code of ethics or skilled conduct policies  They must also seek the advice of their financial planner or wealth manager to achieve the utmost advantage of this potentially lucrative component of compensation.

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