- Using Stock To Exercise Options - FindLaw
- How to Use a Stock Swap to Exercise Employee Stock Options
- Exercising Stock Options - Fidelity
- Exercising stock options: Everything you should know | Carta
Prior to the stock swap, you had owned 65,555 long-only shares and the option to purchase 5,555 shares from the ESO. You “controlled” 65,555 shares.
Using Stock To Exercise Options - FindLaw
This is because these shares often have different tax rules subject to holding period requirements. These requirements and subsequent tax rules can make using shares received through an ESPP and ISOs in a stock swap more complicated than other methods.
How to Use a Stock Swap to Exercise Employee Stock Options
Since you sold 6,555 of your ESO to cover the cost, you retain the remaining 9,555. Post cashless exercise, you own 65,555 previously owned shares and 9,555 shares from the exercise and hold, for a total of 69,555 shares
Exercising Stock Options - Fidelity
You can use long-only stock to exercise incentive stock options, too. Like NQSOs, the tax rules regarding an exercise of incentive stock options, or ISOs, are the same whether you exercise via a stock swap or via another method.
Exercising stock options: Everything you should know | Carta
After the stock swap, you have 9,555 long-only shares and 5,555 newly acquired shares from the exercise and hold of the ESO. You now “control” 69,555.
A cash exercise may be a preferable strategy to stock swap if you are bullish on your company stock and want to retain as many shares as possible. With a cash exercise, you retain more shares post-exercise than you do with a stock swap.
If you had waited to sell your stock options for more than one year after the stock options were exercised and two years after the grant date, you would pay capital gains, rather than ordinary income, on the difference between grant price and the sale price.
If you held 65,555 long-only shares and wanted to exercise 5,555 ESOs, you will use fewer than 5,555 long-only shares to exercise and hold 5,555 employee stock options.
Also, if you leave your company after early exercising but before the stock vests, your option grant usually gives the company the right to repurchase your early-exercised but unvested stock.
If you want to limit your position in a stock, a stock swap may be a zero-cash-required way to exercise your ESOs and reduce your overall exposure to a single stock. If you want to maximize your concentrated position , you may want to pass on a stock swap and use cash to exercise your ESOs.