Question

Is a cashless exercise better than a stock swap?

Answer

The right choice depends on your specific financial situation. A cashless exercise is simpler but may trigger immediate capital gains or ordinary income taxes, especially with incentive stock options (ISOs), which can cause a disqualifying disposition. A stock swap may offer better tax deferral but requires meticulous tracking of basis layers and holding periods.

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We exist so you don’t have to worry about money. For more than 40 years, we’ve taken the sophisticated, time-tested approach that many ultra-high net worth individuals use to help manage their financial lives and made it accessible to more families.

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