Exercising options in a company with no market to sell those shares is a recipe for bankruptcy. Exercising an option is a taxable event, regardless of whether y

Exercising options in a company with no market to sell those shares is a recipe for bankruptcy. Exercising an option is a taxable event, regardless of whether you sell the result shares to receive cash. If you try to anticipate an exit by exercising options early to minimize tax, you might find yourself with a hefty tax bill and no way to pay it should that exit not actually materialize. When dealing with stock options the best advice is, IMO, always to exercise and immediate sell enough of the stock to cover the result tax hit.