Who We Serve
ISO & RSU Holders
Your compensation is concentrated, illiquid, and taxed on a schedule somebody else set.
Incentive stock options, restricted stock units, NSOs, ESPP, and founder stock. The vest date is decided by your employer, the tax lands whether or not you sold anything, and every year you hold, more of your net worth sits in one ticker.
The position
What this situation actually looks like.
At $2M and above, equity compensation stops being a benefit and starts being a structural problem. The income is large, it is lumpy, it arrives on a calendar you do not control, and a substantial part of it is taxed at ordinary rates in the year it is delivered rather than the year you choose to realize it.
The people in this situation are usually excellent at their jobs and have almost no time to run the analysis. They know the position is concentrated. They know the withholding looks wrong. They have been told to exercise their options and have never been shown what that does to their alternative minimum tax. So the default happens instead, and the default is expensive.
Almost every lever that matters here sits before the event rather than after it, which is why the conversation is worth having in a quiet quarter rather than in the week the vest lands.
Recognition
The problems you already know about.
If several of these are familiar, the situation is well within what this practice was built for.
The withholding gap
Federal withholding on the first $1 million of supplemental wages each year is typically a flat 22%. If your marginal rate is 37%, the gap surfaces in April, sometimes with an underpayment penalty. Most people assume the employer handled it. The employer applied a statutory default.
ISOs you have not exercised because nobody modeled the AMT
Exercising incentive stock options and holding past year end makes the spread a preference item for alternative minimum tax. You pay real cash on a gain you have not received, in a year you did not plan for it. So the options sit unexercised, the clock on favorable treatment runs, and the decision gets made for you by expiry.
Frozen by what selling would trigger
You know the position is too concentrated. Selling means recognizing gain, so you hold. Holding means the position grows relative to everything else you own, so the stakes rise, so selling gets harder. It is a loop, and it resolves either deliberately or by a drawdown you did not choose.
A vest calendar that ignores your tax year
Grants vest when the grant says they vest. Two large tranches landing in the same calendar year is a materially worse outcome than the same tranches split across two, and nobody at your employer is looking at that, because it is not their problem.
A liquidity window that closes before you are ready
An IPO, a tender, or an acquisition compresses every decision into a few weeks, inside a blackout, at exactly the moment you have least attention to spare. The planning that would have mattered had to be done well before the event was announced.
Advice that stops at the vest
Your CPA files the return that reports what happened. Your employer's chosen financial wellness provider gives you a calculator. Neither of them is responsible for the multi-year sequence, so nobody is.
Less obvious
And the ones that rarely get named.
These surface in the diagnostic rather than in the first conversation, and they are usually the more consequential half.
Your equity and your salary are the same bet
If your employer has a difficult year, the stock falls and your job becomes less secure in the same quarter. Concentration in your employer's shares is not diversified by your salary. It is doubled by it.
The AMT credit you may already be owed
Alternative minimum tax paid on an ISO exercise generally creates a credit carried forward against regular tax in later years. A surprising number of people who paid it never recover it, because nobody tracked it across preparers.
Section 1202 may be on the table and untested
If your shares are in a C-corporation that was small when they were issued, qualified small business stock treatment may be available. It turns on facts established at issuance, it requires a holding period, and it is frequently discovered after the sale, which is too late.
Your state has an opinion about all of this
Where you were resident when equity was granted, when it vested, and when it was sold can each matter separately. Moving does not settle it, and several states will want to talk about the period before you left.
How we work here
The sequence, applied to iso & rsu holders.
The same three stages, in the same order, framed against the situation you are actually in.
- 01
Save
Vesting, exercise, and recognition sequenced against the calendar, with deductions and credits timed for the years your income actually spikes.
Save in detail - 02
Protect
The tax consequences of how proceeds are held and titled, modeled before anything moves and coordinated with your own counsel.
Protect in detail - 03
Grow
The tax cost of reducing concentration modeled before you sell: lot selection, timing across tax years, and state sourcing. Which shares to hold is a question for your investment adviser, not for us.
Grow in detail
Common triggers
When people tend to call.
- A large vest landing this year that will push you into a bracket you have not planned for
- ISOs you have not exercised because nobody has modeled the AMT consequence
- More of your net worth in your employer's stock than you would ever choose deliberately
- A pre-IPO or pre-transaction window that closes before you are ready to use it
- Withholding set at a default rate that leaves you owing in April
- Two grants vesting in the same calendar year that could have been split
- Wanting to diversify, but frozen by what selling would trigger
Further reading
Written for this situation.
Alternative Minimum Tax and the Cost of a Good Year
Exercising incentive stock options can create a cash tax liability on a gain you have not received. The rules governing that liability moved against high earners, and much of the equity-compensation commentary in circulation still describes the old regime.
Three States That Will Not Follow
California, Illinois, and New Jersey each break the central federal planning move, and they break it in three different ways. Only one of the three is a timing problem.
The Limit Nobody Models
A large first-year deduction is worth very different amounts to two taxpayers with the same income this year and different income next year. The provision that decides it moved against taxpayers in 2026, and almost nobody has noticed.
Not quite your situation?
Begin
Bring us the situation you are actually in.
Thirty confidential minutes with a principal. We will tell you where the real levers are, including when the answer is that you do not need us yet.
Engagements typically begin at $2M+ of annual income, or a comparable taxable event.