What are Incentive Stock Options (ISOs)?
An ISO (also called statutory or qualified stock option) is a type of employee stock option that gives an employee the right to purchase company stock at a certain price called the exercise or strike price.
ISOs only apply while you are still employed at the company, and you will have 90 days to exercise after leaving. Any extension of that expiration date will result in your ISOs flipping to NSOs.
Due to their favorable tax treatment for most people, the amount of ISOs eligible for exercise each year is limited to $100,000. This is calculated by multiplying the number of shares eligible for exercise in any given year by the exercise price. The rules are especially troublesome for companies who utilize a 1-year cliff on their option grants because the entire first year's worth of shares plus all shares vesting in the 2nd year will apply towards the $100K Limit. This limit causes larger grants to be split into ISOs and NSOs.
How are ISOs Taxed?
ISOs are eligible for special tax treatment. When you exercise a stock option, there is a spread between the exercise price and the current Fair Market Value (FMV) that is subject to tax. When exercising ISOs you are exempted from paying ordinary income tax on the spread. However, exercising an ISO is subject to Alternative Minimum Tax, which comes into play for wealthier tax payers or when the spread is large. Additionally, AMT will only be a factor for wealthier tax payers or when the spread between the current FMV and the strike price is large (the AMT exemption recently changed due to 2018 Tax Reform). AMT tax won't be assessed until you pay your taxes the following Spring.
If he ISOs are sold during the same tax year as the exercise, then you will pay ordinary income tax on the spread between the exercise price and the actual sale price. This will be a disqualifying disposition and you will no longer be subject to AMT on the spread between the exercise price and the FMV. Moreover, you aren't subject to payroll taxes either even though you are taxed at the ordinary income rate. If you sell shares resulting from an ISO after the year of exercise but within a year of exercise or within 2 years of the grant, it is also a disqualifying disposition subject to ordinary income tax, but you are still on the hook for AMT in the tax year of the exercise. This is a form of Double Taxation.
If you sell ISOs after the tax year of the exercise, then you will be subject to AMT for the year of the exercise AND be subject t capita ains tax and/or ordinary income tax on the profits from the sale for that subsequent tax year. Those taxes are calculated based on the spread between the final sale price and the exercise price and the FMV at the time of exercise even if you have already paid AMT on the spread between the FMV and the exercise price. Recovering the AMT via credits on an ordinary income tax return could take a long time.
If shares resulting from an ISO are sold at least 1 year after the exercise and 2 years from the grant date, then the sale qualifies for long-term capital gains treatment on the spread between the exercise price and the final sale price. When ISOs are sold in a disqualifying disposition, then ordinary income tax is paid on the spread between the final sale price and the exercise price. ISO's are also not subject to medicare and social security taxes. There is no offset for the ordinary income tax gains from selling your ISOs except for the maximum $3000 ($1500 if married filing separately) allowance of capital losses against ordinary income.
If you hold employee stock options or restricted shares in a private company funded by institutional venture capital, feel free to contact us at the Employee Stock Option Fund for ways to reduce stock option taxes or more information on how we can assist you. By doing so, you can not only avoid the risks associated with investing directly in a startup but possibly improve your taxes as well. For specific tax related support related to stock option exercises, please contact Scott Chou.
For more information on how to monetize your private company equity, please contact us at the Employee Stock Option Fund.