Making Sense of Equity Compensation

September 25, 2019

Equity compensation allows employees to share in the fruits of a business’s collective labor. In addition to providing great incentives for employees to put the team first, equity gives everyone greater participation in a firm’s success. And, if you have the opportunity, equity compensation can be a key contributor on your path to financial independence.

Equity compensation comes in many forms depending on the motives of employers and the stage of the business lifecycle a firm is in:

  • Restricted Stock Units (RSUs) represent an employer’s promise to deliver shares to you as they vest over time, as performance metrics are met, or when other restrictions are removed.
  • Incentive Stock Options (ISOs) provide you the right to purchase employer stock at a stated price and can qualify for preferential tax treatment if certain holding requirements are met.
  • Non-Qualified Stock Options (NQSOs, or NSOs) are like ISOs but they do not come with preferential tax treatment and there are no required holding periods.
  • Restricted Stock awards you immediate and full ownership rights over your shares, but they still vest over a specified schedule.
  • Employee Stock Purchase Plans (ESPPs) allow you to buy employer stock at a discounted price, and the shares can also qualify for favorable tax treatment when you eventually sell, provided required holding periods are met.

Given the rise of equity compensation in the Bay Area alone, we have helped many of our clients navigate the nuances of the different options offered by their employers, even as early as when evaluating different job opportunities. Different taxation rules, third-party valuations, special elections, and more add to the complexity and decision points along the way for consideration.

The Timing of Taxation

One complicating feature of many types of equity-based incentives is that taxation occurs when awards vest—at a time when you may not have the liquidity to cover the tax bill (since you haven’t sold the company stock yet).

With stock options, delaying the decision to exercise can defer taxation, but can put off qualifying for lower capital gains rates and lead to higher ordinary income taxes in a given year.

It is important to weigh these timing issues, so you can make the optimal decision with the information you have and ensure that you have the resources available to pay any corresponding tax bill.

Sometimes taxation is deferred until a “change of control” event, such as an acquisition or IPO. That means there could be a large amount of taxable income to you all in one year. Even though the timing may be uncertain, we have helped clients in these situations evaluate the possible implications and potential ways to mitigate that tax liability when it occurs.

Public or Private?

The value of a public company’s stock is determined by the market. However, when companies are private, the board and eventually third-party assessors set the valuation that determines the economic benefit of equity compensation for tax purposes (a 409A valuation). This adds additional complexity when evaluating the potential benefit and impact on your overall compensation.

Special Elections

For restricted stock, often used by early-stage startups to attract talent when a firm’s cash needs are tight, there is a special election you can make called an 83(b) election. It can lead to preferential tax treatment; however, this election is irreversible and can cause issues if you later leave the company before all your stock vests.

Vesting Schedules, Lock-Up Periods, and Trading Windows

Vesting schedules, lock-up periods, and trading windows may prevent you from selling company stock when you would like to. So, it is important to have strategies in place that work to mitigate the risk of holding a concentrated position if your company stock is a large portion of your overall wealth.

Accounting for Changes

Changing events—personal and/or employer-related—can always impact your plan or complicate past decisions you can’t undo. For example, new equity incentives will vest over time and may change in form as your firm evolves. As we’ve done many times for clients, we can help you construct contingency plans in case circumstances or timelines change.

Whatever your situation, we can work with you to lay out your options, contextualize each decision within your broader financial and life circumstances, and highlight where uncertainties may lie so you can make more informed decisions. This article only scratches the surface of navigating the “nice-problem-to-have” of equity compensation.

We’d love to hear from you and answer questions as you consider your next steps. Please reach out to your Litman Gregory Advisor or contact us here to discuss your goals and implement a plan to help you achieve financial success.


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