Cashless exercise employee stock options
You have lost faith in your employer's prospects and therefore in its stock. You are overdosing on company shares. You want to avoid getting pushed into a higher stock bracket. Waiting to exercise all your options at once could do just that. Exercising a portion at a time can alleviate the problem. A quick way to estimate the value of your options is to calculate how much you would pocket after exercising them and immediately selling the shares. Remember also that income tax will be due on that gain. It's vital to remember that when you hold onto shares that have been converted from exercised options, it is the same as making an investment in the stock. If you're not comfortable with the possibility of a decline, don't hold onto the shares. This is the most straightforward route. You give your employer the necessary money and exercise stock certificates in return. What if, when it comes time to exercise, you don't have enough cash on hand to buy the option shares and pay any resulting tax? Some employers let you trade company stock you already own to acquire option stock. This strategy has the additional benefit of limiting your concentration in company stock. You must have held the swapped ISO shares for the required one- and two-year holding periods to avoid having the exchange treated as a sale and thus incurring tax. This is a case in which you borrow from a stockbroker the money needed to exercise your option and, simultaneously, sell at least enough shares to cover your costs, including taxes and broker's commissions. Any balance is paid to you in cash employee stock. Most stock quote data provided by BATS. Market employee are shown in real time, except for the DJIA, which is delayed by two minutes. All times are ET. FactSet Research Systems Inc. Certain market data is the property of Chicago Employee Exchange Inc. A Time Warner Company. 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