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Usually, you have several choices when you exercise your vested stock options: Hold Your Stock Options. Initiate an Exercise-and-Hold Transaction (cash for stock) Initiate an Exercise-and-Sell-to-Cover Transaction. Initiate an Exercise-and-Sell Transaction (cashless)
This is called vesting. You can exercise your NSOs as soon as they vest, but you can also choose not to exercise. If you choose to exercise, you can either pay the strike price in cash or, if your company allows it, sell a portion of your shares to cover the cost of exercise (referred to as a ?cashless? exercise).
When and how you should exercise your stock options will depend on a number of factors. First, you'll likely want to wait until the company goes public, assuming it will. If you don't wait, and your company doesn't go public, your shares may become worth less than you paid ? or even worthless.
Exercise your stock options to buy shares of your company stock, then sell just enough of the company shares (at the same time) to cover the stock option cost, taxes, and brokerage commissions and fees. The proceeds you receive from an exercise-and-sell-to-cover transaction will be shares of stock. Exercising Stock Options - Fidelity Investments Fidelity Investments ? stockoptions ? exercise Fidelity Investments ? stockoptions ? exercise
Stock options are canceled: In this case, the options are typically worthless, and employees do not have the opportunity to exercise them. This outcome is common when a company is being acquired in a cash transaction, as the new company may not want to assume the obligation of outstanding stock options.