Author: Richard Archer

10 Simple Tips to Maximize Your Restricted Stock and RSUs

Restricted Stock Units (RSUs)

Incorporating restricted stock and RSUs (restricted stock units) into your financial plan can get complicated. You will need to make plenty of decisions, such as how long you will hold your shares if you should sell them and put them into an alternative investment, or if you will use the money to meet one of your financial goals. 

If your head is spinning, take heart. Here are 10 simple tips to help you maximize your restricted stock and RSUs.

Before We Start, How Do RSUs Work Again (And How Does This Differ From Restricted Stock)?

Restricted stock units (RSUs) are a form of equity compensation that companies grant to employees, in which the employees receive company shares upon completion of a specified vesting schedule. Think of them as a bonus – paid in stock shares instead of cash.

They differ from stock options in that employees do not have to purchase shares at a particular stock price; rather, they are given shares outright once they vest.

By contrast, “restricted stock” is actual stock granted on the award date, but it generally cannot be sold or transferred until it vests. Because you technically own restricted stock at grant (although with restrictions), it may be eligible for dividends and potentially an 83(b) election.

RSUs and restricted stock tie employee interests to the company’s future performance. 

However, if you’re not sure how to fit either of these into your overall financial plan, the following rules should help guide you in determining an ideal approach.

Rule #1: Set Your Goals For Your RSU or Restricted Stock Strategy

In order to make quality decisions, you need to determine what you hope your stock will do for you. 

When you eventually sell the shares, where do you want that money to go? How do your shares and their potential sale fit in relation to your other income, 401(k), and other savings?

When setting your objectives, keep both your timelines and your financial goals in mind. Whether you have restricted stock or RSUs, these awards can help fund key financial priorities, such as: 

  • Paying for education
  • Providing a down payment on a home
  • Growing retirement savings
  • Diversifying existing investments

By outlining these aims at the outset, you’ll be able to make more informed choices about whether to hold, sell, or reinvest your shares. 

You should also consider how RSUs fit into your broader compensation, especially if they represent a large portion of your earning potential. Be sure to keep them on your radar alongside salary, bonuses, and any other benefits you receive.

Rule #2: Know Your Vesting Schedule

It is important to know the dates your grants will vest since you will need to pay taxes on the resulting income. 

If you want to avoid a hefty tax bill, it requires planning ahead. Your vesting schedule will depend on your company and the conditions they place on the stock, but it is usually time-based, requiring you to work at the company for a certain period before vesting can occur.

One helpful approach is to create a timeline or calendar event marking each vest date. By planning around these dates, you’ll have a clearer picture of how your income may spike during certain periods, potentially moving you into a higher tax bracket. 

You might also want to see if your company offers any flexibility in your vesting; for instance, some companies allow for acceleration of vesting in certain circumstances, such as mergers, acquisitions, upon disability, or retirement eligibility. 

Either way, thinking ahead helps with tax planning and allows you to anticipate your tax liability (the amount you’ll need to pay the government when tax time comes) long before you owe it. 

📝 Note: Tax liability is a fancy word for the amount of money you owe in taxes to the government.

Rule #3: Understand the Consequences if You Were to Quit

If you leave your company before your restricted stock vests, you will usually forfeit the unvested grants. 

There can be exceptions to this, so be sure to gather all the details from your company before you make the decision to leave. 

If you have a significant amount of shares that haven’t vested, it might be worth it to stay with your company long enough to benefit from this reward for your service.

Evaluate the current and future value of your RSUs or restricted stock and think about whether staying at the company until a certain vest date could be financially advantageous. If you are planning a career change, weigh the opportunity cost of leaving unvested RSUs behind against the benefits of a new role. 

Sometimes, negotiations with a new employer could include a ‘make-whole’ RSU or stock grant to compensate you for the value you are giving up.

Rule #4: Consider Taxes

Your taxable income will be the market value of the shares at vesting and is subject to federal income tax, Social Security, and Medicare, plus any state and local income tax. 

📝 Note: Taxable income is the part of your income that the government uses to figure out how much tax you owe.

Your company may offer you a few ways to pay taxes at vesting, such as withholding shares for taxes, a sell-to-cover transaction for taxes of a portion of the shares, a salary deduction, or simply a check payment. A 22% standard supplement tax withholding, as a sale from shares vested is fairly common. The standard withholding rate often becomes 37% if your total income exceeds $1,000,000.

When you eventually sell the shares, you will pay capital gains tax on any appreciation the stock has from the vest date until the sale date.  

To further minimize your overall tax liability, consider increasing contributions to tax-deferred accounts—such as 401(k)s, Health Savings Accounts (HSAs), or other qualified plans—during your vesting years. By carefully coordinating these strategies, you can maintain more control over your income and keep your total tax liability in check.

Rule #5: Look Into an 83(b) Election

With restricted stock (not RSUs), you have the option to make a Section 83(b) election with the IRS within 30 days of the grant date.

An 83(b) election allows you to pay taxes on the value of the stock at the grant date rather than the vesting date.

If you believe the stock price will be higher on the vesting date and you are confident you will meet vesting requirements, this can be a beneficial move for you. 

Also, moving the time of taxation to the grant date starts the capital gains holding period earlier, which can make a difference at the eventual sale of the shares.

However, keep in mind that making an 83(b) election does involve certain risks: if the stock doesn’t appreciate or—worse—loses value, you might have paid more taxes upfront than necessary. Additionally, if you leave the company or fail to meet vesting requirements, you generally cannot get a refund on taxes already paid because the election is irrevocable once filed. It’s important to consult with a tax advisor or financial planner to confirm if an 83(b) election aligns with your overall financial goals and risk tolerance.

Rule #6: Tax Rates and Restricted Stock Units

Be sure to anticipate what restricted stock and RSUs will do to your tax rates when you vest.

The extra income could push your income into a higher tax bracket, raise your rate of capital gains tax, and trigger extra Medicare taxes, possibly costing you thousands of dollars. If you plan ahead, you can implement strategies that could keep you in the lower tax brackets.

When you hold restricted stock or RSUs, it’s important to understand their impact on both ordinary income and capital gains taxes. 

Tax rates vary by state—some impose high income and capital gains taxes, while others charge little or none. Your location can significantly influence what you owe. Other factors, such as your total income, the length of time you have held the shares, and your filing status, also play a role.

Typically, the market value of your shares becomes taxable income when they vest, which may increase your federal and state tax burden. (Remember, if you made a Section 83(b) election for restricted stock, the income would have been taxed earlier.) 

After vesting, any additional increase in the share price is usually treated as capital gains.

Selling shares within a year of vesting usually means paying short-term capital gains taxes at ordinary income tax rates (currently 10% to 37% federally).

Wait over a year, and you’ll generally qualify for long-term capital gains rates (currently 0% to 20% federally). Plus an additional 3.8% net investment income tax for those individuals with high income.

Please note: Tax laws and rates can change, and states may have unique rules that affect your final bill. To stay informed, it’s wise to keep track of any changes or work with a financial professional.

Rule #7: RSU Selling Strategy: Decide Whether to Hold or Sell

Whether or not you sell your shares at vesting will depend on multiple factors, such as tax planning, financial planning goals, and company restrictions. 

  • If you sell immediately, you can use the shares to pay for the taxes incurred at vesting. 
  • If you hold your shares, your capital gains tax will be affected when you sell in the future. 

Your decision may be influenced by your cash needs, upcoming life events, and other financial planning factors, including diversification, dividends paid on your stock, and alternative investments. 

If your company is publicly traded, there can be blackout dates that prevent you from trading and stock ownership guidelines that require you to keep a certain amount of stock. With private companies, there are probably restrictions in your grant or SEC rules that will impact when you can sell.

Rule #8: Remember Dividends

Even though you can’t transfer or sell restricted stock until it vests, the stock is still issued to you and in your name, which means you could receive dividends. 

If you have unvested RSUs, this does not apply. 

But when a company pays dividends on outstanding shares of stock, it can choose to pay dividend equivalents on RSUs. These may be deferred or accrued to additional units and then settled when the unit vests.

Rule #9: Don’t Let Company Stock Skew Your Portfolio

It’s a cliché, but when it comes to your portfolio, you don’t want to keep all of your eggs in one basket. You don’t want too much of your net worth tied up in your company stock, and since restricted stock and RSUs vest over time, it’s easy to miscalculate how much of your portfolio is reliant on the success of your company. 

In order to avoid overconcentration, consider working with a CERTIFIED FINANCIAL PLANNER® to determine how much your holdings in company stock contribute to your overall net worth.

A financial advisor can help you tackle concentration risk by building a plan to gradually reduce your holdings in company stock. 

Together, you might set up automatic sales when shares vest, look for opportunities to offset gains through tax strategies, or use hedging tools to manage volatility. 

The proceeds can then be channeled into a well-diversified blend of broad-market funds, bonds, or alternative investments, reducing your reliance on a single stock’s performance. Ongoing reviews help make sure your approach stays in step with your goals, risk tolerance, and changes in the market.

With a more diversified approach, you won’t be betting your financial future on a single stock. And as life changes, regular check-ins will help you stay on track.

Rule #10: Rely on a Professional

Managing restricted stock, RSUs, and everything that comes with them can get complicated fast. From taxes to timing to investment decisions, there’s a lot to think about — and it’s easy to feel unsure about the best path forward.

That’s where we come in. 

At Archer Investment Management, we help tech professionals navigate the ins and outs of equity compensation and build plans that align with their lives and goals. 

If you have ESOs, restricted stock, or RSUs, don’t hesitate to reach out to us to help you maximize restricted stock units (RSUs) and incorporate them into your overall financial picture. 

If you’re looking for clarity and a strategy that ties it all together and takes the guesswork out of managing your restricted stock, we’re here to help.

Click here to schedule a call and let’s talk.

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Understanding Qualifying and Disqualifying Dispositions for ISOs: A Complete Guide

Understanding Qualifying and Non-Qualifying ISO Dispositions

An Important Decision: Should I take a Qualifying Disposition or Sell Earlier, Triggering a Disqualifying Disposition?

If you’ve received Incentive Stock Options (ISOs) from your employer, one of the biggest financial decisions you’ll make is deciding when to sell your shares after you’ve purchased them (a step known as exercising).

Exercising ISOs presents a critical decision: Should you aim for a qualifying disposition or selling earlier, triggering a disqualifying disposition? The choice isn’t just about taxes; it can play a role in your financial goals, such as buying a home or managing risks in your portfolio.

What Are Qualifying and Disqualifying Dispositions?

Qualifying Disposition

A qualifying disposition happens when you sell your ISO shares after meeting two specific holding period requirements:

1. At least one year after the exercise date (when you purchased the shares)

2. At least two years after the grant date (when you received the options)

When you meet both of these requirements, you’ll pay the lower long-term capital gains tax rate (0%, 15%, or 20%, depending on your income) instead of the much higher ordinary income tax rates.

Watch Out! Many people only focus on the one-year holding period after exercise. But don’t forget—you also need to hold them for at least two years after the grant date. Missing this second requirement could mean paying much higher taxes by triggering a disqualifying disposition.

Disqualifying Disposition

A disqualifying disposition happens if you sell your ISO shares too early—before meeting  the two holding periods.

When this happens, your profits are taxed at ordinary income tax rates, which can go as high as 37% for top earners. That’s a big difference from the lower rates when the sale is considered a qualifying disposition.

Qualifying vs. Disqualifying Dispositions at a Glance

Viewing ISOs and Employer Shares from a Portfolio Perspective

It’s exciting to hold stock in your company, but holding too much can be risky. If the stock price drops, your portfolio could take a big hit.

That’s why it’s important to think about your ISOs as part of a bigger picture and make sure your investments are well-balanced to protect your long-term financial health.

The Real Tax Impact: Why It Matters

The difference between qualifying and disqualifying dispositions has a big impact on how much of your profit you get to keep after taxes.

Here’s the breakdown:

    • Qualifying Disposition: You’ll pay the lower long-term capital gains rate (around 15-20% for most people).

    • Disqualifying Disposition: You’ll pay the higher ordinary income tax rate, which can reach up to 37%.

Let’s say you’re in the highest tax bracket. The difference between these rates could mean paying 17% more in taxes—potentially costing you tens of thousands of dollars, depending on how much stock you’re selling.

Struggling to untangle the best time to sell your stock? That’s exactly what we help our clients with every day. Schedule a call with us, and we can help you figure it out.

When a Disqualifying Disposition Might Make Sense

Even though disqualifying dispositions can come with higher taxes, there are times when they make good financial sense.

If you have immediate liquidity needs—whether for buying a house, paying for an emergency, covering education costs, or any other major expense—having money on hand might be more valuable than holding out for tax savings.

Selling early can also help reduce your financial risk.

For example, if you’re worried about your company’s performance, stock market swings, or your own job security, it could be smarter to sell some shares now and diversify your investments rather than waiting just to save on taxes.

Here’s a real-life example:
One of our clients, a Tesla employee, faced an unexpected layoff. They needed money quickly to relocate, buy a bigger home, purchase a second car, and prepare for a baby.

In this situation, selling the shares immediately—even with the higher tax hit—was the right move.

The immediate funds allowed them to meet their needs without unnecessary stress.

Understanding the Alternative Minimum Tax (AMT)

Let’s talk about the Alternative Minimum Tax (AMT), which can complicate ISO decisions.

If you exercise your ISOs but don’t sell the shares right away, you might owe AMT even though you haven’t made any money from selling them.

Here’s how it works: The IRS looks at the “paper gain”—the difference between the price you paid to exercise your options and the market value of the stock. Even if you’re just holding the shares, this paper gain can create a tax bill. It’s one more thing to factor in when planning your ISO strategy.

A paper gain is like potential profit. It’s the difference between what you paid for your stock when you exercised your options and what the stock is worth today.

Even though you haven’t sold the stock or made any real money, the IRS looks at this potential profit and might tax you on it with the Alternative Minimum Tax (AMT). It’s like being taxed on money you don’t actually have in your pocket yet!

(We often refer to this potential profit as “an “unrealized” gain).

Five Key Considerations for Deciding When to Sell Your ISO Shares

There’s no one-size-fits-all answer for when to sell your ISO shares—it all depends on your personal situation and financial planning needs.

    1. Start by looking at your income level. If you’re in a higher tax bracket, the tax difference between qualifying and disqualifying dispositions becomes even more important.

    1. Next, think about market risk. Waiting to meet the waiting requirements for a qualifying disposition might save on taxes, but it also means holding onto your shares longer. If the stock price drops during the holding period, those tax savings could disappear.

    1. To stay on top of things, make sure you keep track of key dates such as your grant date, exercise date, and vesting schedules. Knowing these details can help you plan your sales effectively.

    1. A great strategy to lower risk is “staged selling.” Instead of selling all your shares at once, sell in smaller amounts over time. This approach balances market risk with tax benefits.

    1. Lastly, check how much of your portfolio is tied up in employer stock. Too much can leave you overexposed if your company’s stock takes a hit. Diversifying your investments is key to long-term financial stability.

Remember, tax laws aren’t set in stone

Tax laws change, which could affect how you plan your ISO sales. Changes to capital gains tax rates or AMT rules might also impact your strategy.

Staying informed about these potential shifts by working with a CERTIFIED FINANCIAL PLANNER® is important so you can adapt your plan and avoid surprises.

Next Steps

To make informed ISO decisions, take a close look at your grant dates and exercise dates, calculating the tax impact of a qualifying versus selling early to trigger a disqualifying disposition, and consider any immediate liquidity needs. Your risk tolerance also shapes your approach.

Once you have a clear sense of your financial picture, set a timeline for exercising and selling  your shares based on the current market and your company’s performance.

Working with a CERTIFIED FINANCIAL PLANNER® experienced in equity compensation can help align your ISO strategy with broader financial goals, while a tax professional can provide tailored advice for your situation.

The Bottom Line

Guide to understanding qualifying and disqualifying dispositions

Qualifying dispositions can be a great way to save on taxes, but they’re not always the right choice. The best decision balances tax savings with your personal needs and financial goals.

Sometimes, it’s worth paying a little more in taxes if it helps you meet a big life goal, reduce risk, or feel more financially secure.

Need help developing a custom ISO strategy?

Reach out to our team at Archer Investment Management to schedule a consultation.

We specialize in helping tech professionals make smart, confident decisions about their equity compensation.

Schedule a call with our team.

Editor’s Note: This article was originally published on August 15th, 2022. It has been updated to offer an expanded scope of the subject area.

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