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Exercise Period: This is the duration when the employee has the right to 'exercise' their options and purchase company stock. It begins on the grant date and terminates on the expiration date, as detailed in the ESOP agreement.
Form W-2 (or 1099-NEC if you are a nonemployee) Your W-2 (or 1099-NEC) includes the taxable income from your award and, on the W-2, the taxes that have been withheld. This form is provided by your employer. Form 1099-B This IRS form has details about your stock sale and helps you calculate any capital gain/loss.
If you believe the stock price will rise over time, you can take advantage of the long-term nature of the option and wait to exercise them until the market price of the issuer stock exceeds your grant price and you feel that you are ready to exercise your stock options.
For nonstatutory options without a readily determinable fair market value, there's no taxable event when the option is granted but you must include in income the fair market value of the stock received on exercise, less the amount paid, when you exercise the option.
The income related to the option exercise should be included in the Form W-2 you receive from your employer or 1099-NEC from the company if you are a non-employee. Any capital gain or loss amount may also be reportable on your US Individual Income Tax Return (Form 1040), Schedule D and Form 8949 in the year of sale.
As with other types of stock options, when you're granted NSOs, you're getting the right to buy a set number of shares at a fixed price, also called the strike price, grant price, or exercise price. A company's 409A valuation or fair market value (FMV) determines the strike price of an option.
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.
Typically, the short answer is, you should exercise and immediately sell your NSOs once you're within a year or two of their expiration date. Since NSOs typically expire after 10 years, this means you'll usually want to exercise and sell them in their ninth or tenth year.