Rethinking Whether to Exercise and Hold Non-Qualified Stock Options for Long-Term Capital Gains

When it comes to evaluating strategies to exercise your Non-Qualified Stock Options (NQSOs), what is your best plan of attack? Do you: Exercise and sell all your NQSOs immediately, cashing out the full proceeds? Exercise your NQSOs and hold shares of stock, hoping the stock price will go up? Or, leave your NQSOs unexercised and hope the stock price will go up? If you anticipate a higher stock price in the future...

If your employer has granted you incentive stock options (ISOs), you’ve likely spent time researching the tax treatment. If so, you’ve probably read about the alternative minimum tax (AMT), and qualifying and disqualifying dispositions. Perhaps the complication has left you wondering: What does this mean to me as a taxpayer?

If you’re wondering how to maximize the value of your incentive stock options (ISOs), non-qualified stock options (NQSOs), restricted stock units (RSUs), or other forms of equity compensation, you’re not alone. After all, there is plenty to think about if you’ve been granted equity compensation. You may dream of how to strike it rich. You may fear you’ll do something wrong and miss out. You might become mired in taxing technicalities, including AMT calculations. All that thinking can backfire if “TMI” (too much information) prevents you from proceeding.

Non-qualified stock options and incentive stock options are the two types of employee stock options that you may receive as part of your compensation package. While they have some similarities, they also differ, particularly when speaking to how they may be taxed at exercise and upon the final sale of stock.

Wouldn’t it be great if your company stock price only ever went up—especially if you’re participating in its growth through incentive stock options (ISOs)? Unfortunately, that’s not always how the world turns. If the share price goes down instead, you may be bummed to see the value of your incentive stock options is less than what it once was. However, a down stock price might mean that you could score some tax breaks if you exercise and hold some of those ISOs. When the price is down, the move might help minimize alternative minimum tax (AMT).

Who doesn’t love a great tax break? You and I can’t personally reverse a bear market or revise Federal regulations. But we do get to decide when and how to exercise, hold, and sell our incentive stock options (ISOs), dictating whether we have a qualified disposition or disqualified disposition. Why not make best use of your tax-planning powers when you do?

If you are lucky enough to be granted incentive stock options (“ISOs”) as part of your compensation package, it’s important to understand the timeline of events. 

Incentive stock options are a type of equity compensation you may receive as part of your overall compensation package. Incentive stock options, or ISOs, allow you to buy company stock at a fixed price for a set period of time, regardless of the current fair market value of the stock. In the best circumstances, incentive stock options can be a tool to generate significant wealth if...

If you are on the receiving end of an equity compensation award, you may be overwhelmed by the amount of new information, jargon, and rules coming your way. You might also feel uncertain about how new.

Incentive stock options are a powerful compensation tool that can help you grow your wealth. Companies award them to employees as a retention vehicle, to reward specific successes or as an incentive when trying to attract new employees. There are several advantages to incentive stock options. Because they can provide you with a significant opportunity, it’s important to understand them more fully. The Mechanics of an Incentive Stock Option To begin with, it’s helpful to...