Maximizing the Value of Your Equity Compensation: A Guide to Making the Right Choice for You

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.

To achieve this win-win ideal, it’s important to be deliberate about which equity compensation share lots you donate, as well as whether you donate them as post-sale cash proceeds, or unsold shares. We concluded that cash isn’t necessarily king when donating to a DAF. Directly donating low basis, long-term shares usually reigns supreme.

If there’s such a thing as a match made in philanthropic heaven, it may be the ability to donate a portion of your equity compensation shares to a Donor Advised Fund (DAF). DAFs are relatively easy to fund, easy to manage, and they ensure that you get a tax deduction for the full, appreciated value of your donated stock.

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 have equity compensation and are in an abnormally high-income tax year, it often makes sense to consider how you may be able to offset that pending tax liability.

Being part of an initial public offering, or IPO, is an exciting time. This is when a private company goes through the process of getting listed on a publicly-traded exchange. Where shareholders may have previously only been able to buy or sell the company’s equity in private deals (if allowed by the company), an IPO allows for company stock to be bought, sold, or traded...

If you work for a private company and receive restricted stock units as part of your compensation package, that equity compensation may have a double-trigger provision. While not all restricted stock units, or RSUs, come with this feature, it’s an important element to understand. What Are Double-Trigger RSUs? Double-trigger restricted stock units are those that...

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.

If you have equity compensation, you may wonder how the value of the shares you hold may influence your tax bill -- or how vesting, exercising, and selling your shares may impact the value of your award..

Equity compensation and employee stock benefits can be a great tool for employers to attract and retain key talent. These benefits can be equally attractive for employees, because they fast-track your ability to grow wealth if the company’s stock price rises when you can hold and sell shares. But that’s a big “if.” Stock prices...