Should a Startup Allow Early Exercise of Stock Options?

Startups that allow the early exercise of stock options help minimize their employees’ tax liabilities and increase the return on common stockholder equity. At Capbase, we believe there is no downside to a new company permitting the early exercise of stock options as part of their equity purchase agreement.

Early exercise allows employees and founders to essentially purchase common stock under the terms of various types of equity options packages before they are fully vested, thus translating those options into real shares that may now be allowed to mature and be taxed as long term gains when they are sold in the future.

Until they vest, however, they may not be sold, nor do they confer voting rights. There is, of course, some tax liability involved with early exercise, but if used correctly, early exercise could allow an employee to pay closer to 20% tax rather than the 50% tax they might be liable for if their options are exercised at the time of their vesting.

There are some that would argue against allowing early exercise, but these arguments are largely based on incorrectly deployed early exercise strategies. With a complete understanding of employee stock options and a cogent equity plan, if shares are properly priced, there should be no egregious tax liability at the time of exercise.

Thanks to Capbase’s cap table management and filing solutions, concerns that adding new shareholders to the cap table can cause confusion and record-keeping difficulties are no longer of concern.

The typical compensation package for a startup today should include information to educate your employees on the basics of early exercise so they can take advantage of what it has to offer and make their own informed decisions.

In a later stage company, Restricted Stocks or RSUs may be awarded to founders and employees (see Employee Stock Compensation: Equity vs. Options for finer distinctions between these two), but in most early stage companies, their equity grants are made as Stock Options, which provide the right to buy company shares at a predetermined price.

In most cases, these options will either be ISOs or Restricted Stocks (sometimes called Restricted Shares), each of which will come with a vesting schedule which dictates when the holders can exercise the options and buy shares. When options vest, shares of stock may be bought at the predetermined price—known as the exercise price or the strike price. If an employee leaves a company before their stock options vest, the company may repurchase the unvested stock.

For a comparison of ISOs versus another common type of option—non-qualified stock options (NSOs)—see our guide ISO vs. NSO: Which Are Better for Employees?

The stock option grant price for Qualified Incentive Stock Options (ISOs) must be equal or less than the FMV at the date of the grant, so in early stage companies, they are generally very inexpensive to exercise. If you allow your employees early exercise, they will only be liable for AMT (Alternative Minimum Tax) on the spread between the exercise price and FMV, which will in most cases be zero.

If your employees plan to early exercise their ISOs, they must file an 83b election within 30 days of the grant date to get special tax treatment. After they have been early exercised, ISOs are taxable at the long-term capital gains rate if their holding period is 2+ years since their date of grant and 1+ year since their date of exercise.

Otherwise, ISOs will be taxed as ordinary income. In a certain year, any ISO stock issued over the amount of $100,000 will automatically become another class of stock, NSOs, which have different tax obligations. See our article on NSOs vs. ISOs for more info on the difference between the two.

Restricted Stocks are taxed in a similar way and do not need to be held more than 1 year to be eligible for long term capital gains taxes in the case of early exercise.

Consider this example of two employees at the same company, Cluster Engineering Co.:

As you can see, Cluster Engineering Co. is a rather successful company, and has received not one but two 409a valuations in the calendar year. Though both Jesse and Michael started at the company at the same time with the same 1 year vesting schedule, Jesse was allowed early exercise of his Restricted Stocks, while Michael was not. Both were granted 5,000 shares and sold their shares for $3.00 per share at the same time in 2025.

Since Jesse early exercised, he will incur no tax liability in the year in which he purchases his shares. As his $.005 per share price was equal to the FMV of the shares at the time of purchase, the exercise of his shares does not trigger any tax payments.

When he sells his shares in 2025, he will pay long term capital gains on the income from the sale of his shares, which we’ll assume is 15%, though it may vary in practice. At this rate, the final value at which he sold, $3.00, means his tax burden from the sale of his shares in 2025 would be $2246.25.

So, Jesse’s total tax burden was $2,246.25 and his total take home earnings from selling his shares come to $12,728.75.

Michael, on the other hand, chose not to early exercise his shares and ends up purchasing them when he leaves the company for a new job in 2024. The share price increases to $2.00 per share by 2024. As a result, when Michael exercises his shares, he will pay AMT of 28% on the difference between the fair market value of his shares in 2024 ($2.00) and the price he was granted the shares in 2020 ($0.005). With 5,000 shares, Michael will be on the hook for a tax bill over $2,700 in the year in which he purchases his shares.

When Michael goes to sell his shares in 2025 when the prices is $3.00 per share, he will also pay normal income tax on the sale of his shares. This is because he will not have held the shares for long enough to qualify for these earnings to be taxed as long term capital gains.

Most technology workers are in higher income tax brackets in the United States, so they usually pay at least 24%, up to as high as 37% income tax. Let's round this out and use 30% as a number for Michael's tax taxes. In 2025, Michael will be on the hook for 30% of his profits from selling the shares, for a total of over $4,400.

By not early exercising his shares, Michael ends up paying stock at the time he exercises his shares in 2024, around $2,700. Then, Michael will pay an additional $4,400 when he sells his shares in 2025. His overall tax burden is $7,100 and his take home earnings of $7,875 (after taxes are deducted) are substantially lower than Jesse's.

Comparing the two outcomes here, because Michael did not early exercise his shares, he ended up paying an effective tax rate of around 47%. Meanwhile, Jesse was able to keep more of the proceeds from the sale of his shares, paying an effective tax rate of only 15% to the Internal Revenue Service.

While the figures in these examples are small, keep in mind that as the amount of stocks awarded goes up, the discrepancy can become quite extreme. To get more realistic picture of the tax situation for some early employees of successful startups in the United States, one could an extra zero or two to the dollar amounts in the examples above.

Years ago, as the first engineer hired at a growing startup, I purchased a significant number of my shares after they had already vested when I was leaving the company—my tax bill ended up being over $60k and I had to sign up for a payment plan from the IRS in order to pay down my tax liability. I wish I had known more about early exercise at the time!

• Most early stage companies prefer to issue employees equity compensation as ISOs and executives Restricted Stocks.
• Both ISOs and Restricted Stocks are eligible for an 83(b) election which minimizes immediate tax liability.
• In a certain calendar year, any stock granted over $100K is qualified as NSO by default.
• You must hold ISOs at least 2 years from the date of grant to qualify for taxation as a capital gain. Restricted Stocks must only be held one year.