What is equity compensation and how does it work?

Equity compensation is a form of pay tied to company ownership, often in the form of stock options or RSUs. Each type has its own rules around vesting, taxation, and timing, which directly impact how and when compensation becomes usable wealth. The complexity often increases over time as multiple grants and decisions begin to overlap.

When should I exercise my stock options?

There is no single right time to exercise stock options. The decision depends on your tax situation, cash flow, company outlook, and overall net worth concentration. Exercising too early or too late can create different tax outcomes and risk exposures, which is why evaluating multiple scenarios is important.

RSUs are typically taxed as ordinary income when they vest, based on the value of the shares at that time. Any additional gain or loss after vesting is taxed as capital gains when the shares are sold. Withholding is often applied but may not fully cover the total tax liability.

Should I sell my RSUs when they vest?

A helpful way to evaluate this decision is to consider whether you would choose to buy your company stock if you received the same value in cash. Holding RSUs without a clear strategy can lead to unintended concentration over time, especially when equity compensation continues to accumulate.

How much of my net worth should be in company stock?

There is no universal percentage that applies to everyone. The appropriate level of company stock exposure depends on your financial situation, career stability, and long-term goals. Equity compensation can build gradually, which can lead to over-concentration if not evaluated intentionally.

At what point does equity compensation become complex enough to need guidance?

Equity compensation often becomes more complex as multiple grants accumulate, income increases, and a larger portion of net worth is tied to company stock. At that stage, decisions around exercising options, managing tax exposure, and handling concentration risk begin to interact in ways that are not always obvious.

wealth management for women & families

Equity Compensation Planning

Equity compensation can be one of the most powerful wealth-building tools available. It can also be one of the most confusing.

Schedule Consultation

Equity compensation requires a strategy.

Decisions with consequences

Timing

Reclaiming the Clock

Equity isn't a reward if you’re too exhausted to enjoy it. We move you away from the "wait and see" trap that keeps you tethered to a corporate calendar. By defining clear exit windows and cash flow milestones ahead of time, we ensure your liquidity is driven by your personal goals, not by the inertia of a vesting schedule or market volatility.

Precision

Making Your Equity "Real"

You’ve spent years building value for your company. Precision is how you finally claim that value for yourself. We move beyond generic "hold or sell" advice to model exactly how your shares integrate with your life. By quantifying your exposure and setting clear execution targets, we ensure your transition from employee to owner is handled with the same high standards you bring to your own work.

Tax Intelligence

Protecting Your Private Reserve

The IRS is a silent partner in your compensation, but they don't have to be the majority shareholder. We orchestrate your vesting and exercise dates across a multi-year horizon to shield your earnings from the highest brackets. By proactively eliminating the "April surprises" that plague DIY planning, we help you keep the maximum amount of what you’ve rightfully earned.

We help turn your equity into your financial autonomy.

You’ve earned the equity, let’s own the outcome.

Visibility & Flow

Vesting & Liquidity Mapping

We translate complex vesting schedules into a high-definition cash flow roadmap. By modeling your upcoming wealth events, we ensure you have a strategic view of when your equity becomes "real," allowing you to fund major life milestones without the guesswork or the anxiety of a shifting market.

Capital Preservation

Eliminating the "April Surprise."

High-value vests often come with under-withholding traps that lead to massive, unexpected tax bills. We provide the specific calculations and quarterly payment strategies needed to stay compliant without draining your cash flow. We turn a chaotic tax season into a non-event.

Risk Mitigation

Defeating the "Golden Handcuffs"

Concentrated stock positions are a silent trap for your long-term freedom. We quantify your exposure and design a disciplined exit strategy that protects your family’s lifestyle, ensuring your future is never held hostage by a single company’s stock price or a change in management.

Life Alignment

Funding Your Autonomy

Whether you’re eyeing a career pivot, a sabbatical, or a legacy move, we align your liquidity with your intent. We turn corporate compensation into a tangible lever for your personal freedom, ensuring your wealth supports your vision for the future, not just your employer's bottom line.

Equity Compensation CASE STUDy →

Emily
Maximizing Career & Benefits

Black and white portrait of a woman with shoulder-length wavy hair and bangs, smiling with exposed teeth, wearing a dark blazer and a delicate necklace.

High-growth careers bring unique rewards and unique pressures. Emily found herself navigating the complexities of equity compensation and a major career pivot while trying to keep her family’s future in focus. This case explores how we helped her move past decision fatigue to align her concentrated wealth with her long-term vision.

Read Her Story

Frequently asked questions about equity compensation.

Equity compensation is a form of pay tied to company ownership, often in the form of stock options or RSUs.
Most people understand the basics. The complexity tends to build quietly over time as multiple grants overlap and decisions start to interact.
At a certain point, it becomes less about understanding what you have and more about how those decisions affect each other, especially from a tax and risk perspective.
That’s typically when people step back and realize they want a more structured approach rather than continuing to piece it together on their own.
There isn’t a single “right” time to exercise your stock options. It depends on your tax situation, your company’s outlook, your cash flow, and how concentrated your net worth already is.
The decision can materially affect your tax exposure and overall risk, and in some cases the timing is not easily reversed once action is taken.
What we see most often is people making this decision in isolation or based on partial information, especially as their compensation becomes more meaningful.
As the stakes increase, many prefer to step back and evaluate the full picture rather than continuing to carry that decision-making on their own.
RSUs are typically taxed as ordinary income when they vest, based on the value of the shares at that time.
Any additional gain or loss is taxed as capital gains when the shares are sold.
Where this becomes an issue is that withholding is often not aligned with your actual tax rate, which can lead to underpayment that only becomes clear later.
Many high earners assume it’s handled and only realize the gap at tax time.
This is one of those areas that feels straightforward early on, but becomes more important as income and grant size increase.
A useful way to think about this is:
If you were paid this amount in cash, would you choose to buy your company’s stock today?
Most people don’t naturally frame the decision this way and end up holding without a clear strategy.
Over time, that can lead to a level of concentration that doesn’t align with their broader goals and isn’t always obvious as it builds.
As portfolios grow, many people prefer to have a consistent framework guiding these decisions rather than revisiting them each time a grant vests.
Equity compensation often builds quietly over time, often without a clear point where it feels urgent to address.
At a certain point, your income, your career, and a meaningful portion of your net worth are all tied to the same company.
That level of exposure can work in your favor, but it also increases downside risk in ways that aren’t always obvious until they matter.
This is typically when people want a more intentional plan around how and when to diversify.
Most people don’t start out feeling overwhelmed by equity compensation.
The shift tends to happen gradually as multiple grants accumulate, income increases, and more of your net worth becomes tied to your company.
At that point, decisions around exercising, tax exposure, and concentration risk begin to interact in ways that are not always easy to unwind.
That’s usually when people decide they don’t want to carry those decisions alone and prefer a more structured, coordinated approach.