For executives paid in equity
Plans built around how you are actually paid.
Vested RSUs are withheld at a flat 22% on the first $1 million, even when salary already sits in the 32% or 35% bracket. That gap is one of many in equity pay. We work with the structure of your compensation directly: the calendar, the tax, and the concentration.
The situation
Every grant pulls on the next decision.
Your pay arrives on a vesting calendar that never sits still. Grants, options, an ESPP, a bonus, perhaps deferred compensation, each with its own tax rule, and a growing share of your net worth sitting in one company’s stock.
The pieces interact. An exercise changes the tax bill, the tax bill ties up cash, and selling to reduce concentration changes what you owe again. Each statement shows one piece alone, so the hard decisions get postponed because they are complicated.
We put every date and every rule on one page, then decide in order.
Why it’s complex
Five places equity pay goes wrong
Withholding and the bracket disagree
Each vest is ordinary income withheld at 22%. If your bracket is higher, the difference arrives at filing. We size the gap each quarter and plan estimated payments with your CPA.
See the strategyConcentration builds quietly
Every vest adds to the same position. Without a stated ceiling, one employer can become half the balance sheet before anyone decides it should.
Read the guideThe tax should not decide alone
Holding a low-basis position to avoid the gain is itself a risk decision. Sometimes paying the tax is the price of restoring flexibility.
Read the guideDiversify around the position
A personalized index portfolio can exclude your employer’s stock and harvest losses that offset gains from selling it, spreading the exit across several years.
See the strategyAn early exit changes the math
Leaving an employer in or after the year you turn 55 lets that plan’s withdrawals skip the 10% penalty. Rolling the balance to an IRA forfeits the exception.
Read the guideSources: IRS Publication 15 (2026); IRS Rev. Proc. 2025-32; IRC §423; SEC Release 33-11138.
Our approach
Decisions set to the vesting calendar
We start with every grant agreement, vest date, strike price, and trading window, connected to the rest of the balance sheet. Then we set rules that run on their own, so each vest becomes a routine rather than a decision.
Close the withholding gap
Model the difference between 22% withholding and your actual bracket, set estimated payments with your CPA, and adopt a sell-at-vest rule for new shares.
Time the exercises
The spread on an ISO exercise is an AMT preference item. We model exercises across several years against the $140,200 joint exemption, which phases out above $1,000,000 of AMT income, and track the credit that follows. Full long-term treatment requires two years from grant and one from exercise (IRC §422).
Design the selling plan
Directors and officers wait the later of 90 days or two business days after the next 10-Q or 10-K, capped at 120 days, before a 10b5-1 plan can trade; other employees wait 30. We design the schedule and coordinate it with your company’s counsel.
Model the exit
Unvested equity, severance, deferred compensation elections, and net unrealized appreciation on employer stock in the 401(k) are modeled together, with a liquidity bridge to 59½ where one is needed.
The work
What you’ll work through with us
- A single calendar of vests, expirations, blackout periods, and trading windows
- RSU withholding and estimated-payment planning with your CPA
- Multi-year ISO exercise and AMT modeling
- ESPP hold-or-sell decisions inside the concentration plan
- A diversification schedule: systematic sales, gifts of shares, and exchange funds where eligible
- Rule 10b5-1 plan design, coordinated with company counsel
- A net unrealized appreciation review for employer stock in the 401(k)
- Early-exit modeling that includes deferred compensation and severance
Equity compensation planning at the firm is led by Theo Halbardier, CFP®, CIMA®, CAIA®, the firm’s founder. We are fee-only: no commissions, no product sales. About Theo
Questions
Common questions from executives
Is 22% withholding on my RSUs enough?
Often not. Employers withhold at the flat supplemental rate, 22% on the first $1 million of supplemental wages in a year (IRS Publication 15). If salary alone places you in a higher bracket, every vested dollar is taxed at that bracket, and the gap appears at filing. We model the gap and plan estimated payments with your CPA.
Can you help me sell company stock if I am an insider?
We help design the schedule and coordinate with your company’s general counsel on a Rule 10b5-1 plan. We do not give legal advice, and trading windows and blackout rules remain your company’s to set.
What if my options are underwater?
Underwater options are a timing question, not a lost cause. We track the expiration dates, the exercise cost, and the AMT effect so that a decision is ready if the price recovers, and so nothing expires unnoticed.
Should I hold ESPP shares for a qualifying disposition?
It depends on the discount, the holding period, and how much of the company you already own. A qualified plan can discount shares up to 15%, and a qualifying disposition shifts part of the gain to capital-gains treatment. Holding also adds to the concentration the rest of the plan is working to reduce.
Do you handle deferred compensation and severance too?
Yes. Non-qualified deferred compensation elections, severance timing, and unvested equity are modeled together when we build an early-exit scenario.
How are you paid?
We are fee-only. We earn nothing on exchange funds, insurance, or any vehicle used to reduce a position, so the recommendation stays separate from any sale.
Reviewed by Theo Halbardier, CFP® · Updated September 2026 · Figures current for 2026
Bring the grant statements.
The first conversation is 30 minutes. A recent equity statement helps, but no preparation is needed.
Meet with us