Stock FAQs

when to exercise nso stock options start up

by Mr. Major O'Hara III Published 3 years ago Updated 2 years ago
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Since time is often your friend when it comes to stock options, you can simply sit out the first couple of years to allow for growth and start to exercise your NSOs in a systematic way when you are nearing expiration. You can plan on exercising 25% of your options per year, in years 5-9.

Generally speaking, if your startup does well, it's better to exercise your options as they vest. We'll go into the two main reasons why - tax treatment and cash flow – but the quick-and-dirty answer is that if you trust your startup to grow, you're better off exercising your stock options as soon as you can.Apr 7, 2021

Full Answer

What does NSO stand for in stock options?

Non-Qualified Stock Option (NSO) Reviewed by James Chen. Updated Aug 13, 2019. A non-qualified stock option (NSO) is a type of employee stock option wherein you pay ordinary income tax on the difference between the grant price and the price at which you exercise the option.

How much does it cost to exercise a non-taxable stock option?

Let’s take a look at each tax occasion. When you exercise an NSO, you pay the company who issued the NSO the exercise price (also known as the strike price) to buy a share of company stock. If the exercise price is $10 and you have 100 NSOs, you would pay the company $1,000 to exercise your 100 NSOs and the company would give you shares of stock.

When should I exercise my NSOs?

The first step in deciding when to exercise is to look at which NSOs are vested and eligible to exercise. Also, you should not exercise if the current stock price is lower than your option price, (“under water”). Some other factors to consider:

When should I not exercise my stock options?

Also, you should not exercise if the current stock price is lower than your option price, (“under water”). Some other factors to consider: What are your expectations of your company’s growth and stock appreciation?

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When should you exercise NSO stock options?

The most common expiration of NSOs is 10 years, but this does vary from company to company. Since time is often your friend when it comes to stock options, you can simply sit out the first couple of years to allow for growth and start to exercise your NSOs in a systematic way when you are nearing expiration.

When should I exercise my options before IPO?

The best time to exercise (for most people) "You will take the minimum liquidity risk — that is, you have your money tied up the least amount of time without being able to sell — if you don't exercise until your company tells you it has filed for an IPO."

Should I exercise options early?

Exercising your stock options early means that if your company goes public, you'll get more control over the timing of your stock sale. Once your company's lockup period ends, you can decide to sell (potentially at the long-term capital gains rate) or hold onto your shares.

When should you exercise stock options in a private company?

3 Best Times to Exercise in a Private CompanyAnytime the Exercise Price & Fair Market Value are the Same. When your exercise price and the FMV (fair market value) are the same, you'll trigger $0 in taxes… ... Incentive Stock Options: Anytime You Can Avoid the AMT. ... Incentive Stock Options: Right Before the IPO.

When should you exercise options?

Exercising an option is beneficial if the underlying asset price is above the strike price of a call option or the underlying asset price is below the strike price of a put option. Traders don't have to exercise an option because it is not an obligation.

When should I exercise vested stock options?

Assuming you stay employed at the company, you can exercise your options at any point in time upon vesting until the expiry date — typically, this will span up to 10 years.

Should you exercise iso early?

The early exercise of non-qualified stock options has the possibility to achieve the tax benefits of ISOs with a 1-year holding period and without AMT concerns. Some situations where it may be beneficial to consider an early exercise: Spread between the exercise price and FMV is zero.

Do I pay taxes when I exercise stock options?

You have taxable income or deductible loss when you sell the stock you bought by exercising the option. You generally treat this amount as a capital gain or loss. However, if you don't meet special holding period requirements, you'll have to treat income from the sale as ordinary income.

Why is it never optimal to exercise American call early?

For an American call (on a stock without dividends), early exercise is never optimal. The reason is that exercise requires payment of the strike price X. By holding onto X until the expiration time, the option holder saves the interest on X.

What is the difference between an ISO and NSO?

Summary. NSOs (Non-qualified Stock Options) can be used to compensate employees, consultants, directors, business partners, and advisors. ISOs (Incentive Stock Options) can only be used to compensate employees. NSOs are taxed as regular income at the time of exercise and are not eligible for an IRS section 83b election ...

Can options be exercised after hours?

For the most part, options that are in-the-money (ITM) will be automatically exercised at the closing market price. However, it is not mandatory, and investors can contact their clearing firm with an exception that can occur during after-hours trading.

What happens if you exercise your stock options?

If you choose to exercise your stock options, you can hold on to your company shares or sell them.

What is employee stock option?

Employee stock options are a type of equity compensation that gives you the right to buy a certain number of company shares at a specified price upon vesting. Vesting refers to the point in time in which you receive actual ownership of your options and are able to exercise them (purchase company shares).

What is a non-statutory option?

Also called nonqualified stock options, nonstatutory options are taxed upon exercise at income tax rates and again when shares are sold — any gains accrued will be taxed at capital gains tax rates. NSOs can be granted to outside service providers, consultants or advisors.

What is the importance of knowing what type of options you have?

Knowing which type of options you have and understanding the different tax implications of each is crucial, as this information may help you decide when to exercise your stock options.

How long do you have to exercise your options?

Assuming you stay employed at the company, you can exercise your options at any point in time upon vesting until the expiry date — typically, this will span up to 10 years. If you’re leaving your employer, check the fine print in your options contract to see what time frame you have to exercise; this is usually referred to as the “post-termination exercise period.”

What to do if you are overly exposed to your company?

If you are overly exposed to your company shares, you may want to exercise your options and sell your company shares, using those proceeds to diversify your portfolio.

Why do companies have stock options?

Stock options help to align your interests with that of your employer. The higher your company’s share price grows, the more your options will be worth, providing extra incentive to help drive your company’s success.

How long do you have to hold stock after exercising options?

If an employee waits for at least 2 years from the grant date, holds on to the stock for at least 1 year after exercising options, and continues employment in the company for at least 3 months before the sale date, if all these 3 criteria are met, they become eligible for the special long-term capital gain tax rate. If not, an ordinary income tax of 30% is levied.

How Non Qualified Stock Option Works?

When an employee actually becomes eligible to exercise their options will depend on the non qualified stock options vesting. Vesting ensures that employees stay committed to the growth of the company. If the business posts a positive growth, so does the price of stocks. On vesting, an employee has to choose from one of these 3 options:

What is a stock option?

When an employee is granted stock options, it translates as the right to buy company shares at a fixed price on the grant date. This is a special privilege granted to employees of a company in comparison to external shareholders, who if interested, have to buy company shares at the going market price. Stock options provide the employees with an opportunity to become shareholders in their company of employment.

What is strike price?

Strike price: The price at which stock options are given to an employe e on the grant date is the strike price. This is a fixed price offered only to the employee and does not vary with market fluctuations. The idea is that share prices will increase as the business grows. So at a later stage when employees exercise their options at the strike price (which will be lower than the market price on that date), they profit from the difference in prices.

How long does a stock vesting period last?

It can range from 12 months to 5 years.

How long do you have to hold stock options to get capital gains tax?

After exercising stock options, if the stocks are held for less than 12 months – short term capital gain rates are levied (similar to ordinary income tax). If stocks are held for more than a year, long term capital gain rates are levied in the range of 0 to 20%.

How long does a stock option last?

It can range from 12 months to 5 years. Expiration date: After the vesting period, once employees have received complete rights to exercise all of their non qualified stock options, they have to use it within a set time frame. This is the expiration date. Beyond this date, employees lose their claim over these stocks.

What is NSO stock?

A non-qualified stock option (NSO) is a type of stock option used by employers to compensate and incentivize employees. It is also a type of stock-based compensation. Stock Based Compensation Stock Based Compensation (also called Share-Based Compensation or Equity Compensation) is a way of paying employees and directors of a. .

How Do Employers Benefit From Non-Qualified Stock Options?

Non-qualified stock options benefit employers in ways that are similar to all other stock options. By serving as an effective compensation method, it reduces the potential cash outflow and allows the company to retain higher cash and liquidity for other needs. It also acts as an incentive for employees – once they have a vested interest in the company, they are likely to be loyal and motivated to increase the value of the stock.

How long does Sarah hold her shares?

Sarah holds her shares for less than 12 months before selling them. In this case, Sarah would be required to pay the short-term capital gains tax rate on the profits she has made. The rates are typically pegged to tax brackets and are equal to ordinary income taxes. The amount is given by:

What is an ESOP?

Employee Stock Ownership Plan (ESOP) An Employee Stock Ownership Plan (ESOP) refers to an employee benefit plan that gives the employees an ownership stake in the company . The employer allocates a percentage of the company’s shares to each eligible employee at no upfront cost.

How many shares does Sarah have to give away?

The total number of shares she would need to give away is equal to $12,000/$45 = 266.67, or 267 shares.

Do employees pay taxes on NSOs?

As mentioned earlier, employees are required to pay taxes on NSOs when they choose to exercise their options since exercising the options creates a reportable income. The amount that will be taxed is given by:

Does Sarah have to hold her shares for a longer period of time?

Therefore, by holding her shares for a longer period of time, Sarah may have the chance to save on tax payments through the capital gains tax rates. Capital Gains Tax Capital gains tax is a tax imposed on capital gains or the profits that an individual makes from selling assets.

What happens if you exercise stock options without the date?

If the date passes without the options being exercised, the employee would lose those options. There is an expectation that the company’s share price will increase over time. That means employees stand potentially to acquire stock at a discount if the grant price—also known as the exercise price—is lower than later market prices. ...

Why are NSOs called non-qualified stock options?

They are called non-qualified stock options because they do not meet all of the requirements of the Internal Revenue Code to be qualified as ISOs. 2 

Can an employee buy stock at a discount?

There is an expectation that the company’s share price will increase over time. That means employees stand potentially to acquire stock at a discount if the grant price—also known as the exercise price—is lower than later market prices. However, the employee will pay income tax against the difference with a market share price of the stock when the option is exercised. Once the options are exercised, the employee can choose to sell the shares immediately or retain them. 1 

Does Investopedia include all offers?

This compensation may impact how and where listings appear. Investopedia does not include all offers available in the marketplace.

Can you lose stock options if you leave the company?

The terms of the options may require employees to wait a period of time for the options to vest. Furthermore, the employee could lose the options if they left the company before the stock options are vested. There might also be clawback provisions that allow the company to reclaim NSOs for a variety of reasons.

What is exercise in stock options?

A stock option vocabulary: Exercise: The act of purchasing the shares of stock that are underlying to the option. Grant price: The price at which the stock can be purchased under the terms of the option. This is also referred to as the strike price or the exercise price. Under most plans, this is set at the fair market value ...

When do options vest?

The options vest over a period of time and/or when certain individual, group, or corporate goals are met. Once vested, an employee can exercise the option at the grant price at any time over the option term, up to the expiration date.

Why is there a loss on exercise and sell?

Because of mismatches in the way fair market value at exercise is measured and how capital gain or loss is calculated , there is quite often some gain or loss. On an exercise-and-sell transaction, for example, most plan participants have a capital loss equal to the brokerage commission and SEC fees on the sale.

What is the cost basis of a stock?

Once acquired, the shares are assigned a cost basis equal to the fair market value of the stock at the time of exercise. From there, any subsequent gain or loss realized by the employee upon the sale of the shares will be a capital gain or loss.

Can you gain or lose on an exercise and sell option?

If the options are exercised and the applicable shares are sold simultaneously (as is often the case), compensation income will still be recognized, without any, or at most minimal, resulting capital gain or loss on the transaction. Because of mismatches in the way fair market value at exercise is measured and how capital gain or loss is calculated, there is quite often some gain or loss. On an exercise-and-sell transaction, for example, most plan participants have a capital loss equal to the brokerage commission and SEC fees on the sale.

Is NSO taxable?

The recipient of an NSO is not taxed at the time the option is granted, and is taxed instead when the option is exercised. When an employee exercises an NSO, the spread on exercise (the difference between the fair market value of the stock and the grant price of the option) is taxable to the employee in the same year in which the option is exercised. In fact, it’s included in compensation income, along with salaries and wages, and is reflected on IRS Form W-2 for tax reporting purposes.

How Do Non-Qualified Stock Options Work?

Non-qualified stock options are issued at a grant price. The grant price is the price at which you can buy the company stock. If the current market price exceeds the grant price, the non-qualified stock option has value.

What is the goal of stock option?

The goal here is to capture the stock option value immediately and avoid both market risk and concentration risk. Often, the proceeds are then allocated to a diversified investment portfolio* (or some other personal need).

What is vest date?

The vest date is when you (the stock option holder) have the right to exercise non-qualified stock options. Prior to this vesting date, you may not be able to do anything.

What happens if you let stock options expire?

Should you let options that have value expire, you are effectively throwing money out the door.

Why do you want to sell your stock immediately?

Why? Because you may be able to participate in the upside of the company through future options, as opposed to the ones you can exercise now.

What happens if you leave a non-qualified stock option?

If your non-qualified stock options have value but aren’t yet vested, and considering the fact that if you leave the company you forfeit them, you can see where you might be more inclined not to leave your company until you at least get a chance to exercise.

How much does Strategy 2 cost?

Strategy 2 cost $26,400, or $9,000 more. While less tax may be a good thing, there’s a trade-off: you take on additional risk by hanging onto your shares after exercising your options. Specifically, you risk losing the money it cost to exercise and buy the shares and exercise and pay the tax.

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How Non-Qualified Stock Options Work

Taxation and Non-Qualified Stock Options

  • As mentioned earlier, employees are required to pay taxes on NSOs when they choose to exercise their options since exercising the options creates a reportable income. The amount that will be taxed is given by:
See more on corporatefinanceinstitute.com

How Do Employers Benefit from Non-Qualified Stock Options?

  • Non-qualified stock options benefit employers in ways that are similar to all other stock options. By serving as an effective compensation method, it reduces the potential cash outflow and allows the company to retain higher cash and liquidity for other needs. It also acts as an incentive for employees – once they have a vested interest in the company, they are likely to be loyal and mot…
See more on corporatefinanceinstitute.com

More Resources

  • CFI is the official provider of the Commercial Banking & Credit Analyst (CBCA)™certification program, designed to transform anyone into a world-class financial analyst. To keep learning and developing your knowledge of financial analysis, we highly recommend the additional resources below: 1. Employee Stock Ownership Plan (ESOP) 2. Remuneration 3. Restricted Stock 4. Vesting
See more on corporatefinanceinstitute.com

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