Equity compensation and benefits
We connect stock compensation and employer benefits with your taxes, investments and spending, so vesting, exercise and enrollment decisions work together.
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Connect compensation to your plan
Map the decisions and deadlines
We review your stock grants, options and purchase plans, then map their tax rules and decision dates. Withholding, exercise costs and available cash are considered before you commit to the next step.
Plan for company-stock exposure
Your salary, bonus and investments may already depend on the same company. We consider that exposure alongside taxes and the rest of your portfolio, with a deliberate plan for holding or diversifying shares.
Make benefits fit your life
We review retirement benefits, health plans and deferred compensation alongside your savings, debt and education goals. A job change, home purchase or sabbatical can be modeled before you make the decision.
For hands-on help with your budget, explore budgeting and cash flow.
Common questions
My RSUs vested and I owe more tax than expected. What happened?
Most often, withholding. Employers often withhold at the flat supplemental rate, which under-withholds anyone in a higher bracket. It is predictable and it is fixable with estimated payments or adjusted withholding once we model the year.
Should I exercise my options early?
It depends on the type of option, the spread, your alternative minimum tax exposure, your cash position, and how much risk the company already represents in your net worth. This is a modeling question rather than a rule of thumb.
Should I pay off my mortgage or invest?
It depends on your rate, your tax situation, your liquidity, and your temperament. We will show you the math both ways and be honest that the emotional answer is a legitimate input, not a mistake.
How is my stock compensation actually taxed?
Equity compensation is where we see smart, high-earning people lose the most money to preventable mistakes, because the paperwork arrives looking like a benefit and behaves like a series of tax decisions with deadlines.
Restricted stock units are taxed as ordinary income when they vest, at the full value of the shares, whether or not you sell. Employers commonly withhold at the flat supplemental rate, which is well below the marginal rate of most people who receive meaningful RSU grants. The result is a predictable April shortfall that has nothing to do with the investment and everything to do with withholding.
Holding the shares after vesting is a separate decision from receiving them, and it deserves to be made deliberately rather than by default.
Incentive stock options are the ones that punish inattention. Exercising and holding creates a bargain element that is invisible for regular tax and very visible for alternative minimum tax, so a paper gain can generate a real cash bill in a year you received no cash. Getting favorable long-term treatment requires holding at least two years from grant and one year from exercise under IRC section 422, and those dates need to be tracked deliberately.
Nonqualified options are simpler: the spread is ordinary income at exercise. For restricted stock subject to vesting, an election under IRC section 83(b) can be extremely valuable and it generally must be filed within thirty days after the property is transferred to you. Confirm that deadline before the transfer.
Employee stock purchase plans have their own qualifying and disqualifying disposition rules under section 423 that change the character of the gain.
Underneath all of it sits concentration. When your salary, your bonus, your equity, and your largest holding all depend on one company, that is a single point of failure, and unwinding it deserves a written schedule rather than a vague intention.
What about the rest of my financial life?
The unglamorous side of this service is often where the plan is actually won. Consistent saving is the part of the plan you control. Automating it helps keep each month aligned with your goals.
Debt gets analyzed rather than moralized. Whether to pay off a mortgage early, refinance, or invest the difference depends on the rate, your bracket, your liquidity, and how you actually feel about carrying the balance, and reasonable people land in different places. Emergency reserves get sized against the real risk to your specific income rather than a generic number of months.
Employer benefits are reviewed each open enrollment, because those elections are made quickly once a year and frequently leave real money unclaimed, particularly around health plan selection, health savings accounts, and deferred compensation elections that lock for the following year.
Education funding runs through 529 plans, including the front-loading election that lets several years of gifting happen at once. And the large one-time decisions, buying a home, taking a sabbatical, changing careers, or absorbing a period without income, get modeled before they happen rather than explained afterward.
What exactly is included?
- Savings strategy and automation design
- Debt paydown and mortgage decisions
- RSU and option exercise planning
- Education funding and 529 strategy
- Emergency reserve design
- Employer benefits and open enrollment optimization
- Home purchase and major expense planning
- Cash flow modeling for career changes and sabbaticals
- ISO exercise timing and AMT modeling
- 10b5-1 trading plan design
- Nonqualified deferred compensation elections
- Securities-based lending, margin, and HELOC comparison
- Compensation package and job offer analysis
- Custodial accounts and Roth IRAs for working kids