Equity comp · Complex ownership

RSU and stock option tax planning, run as one plan.

Vesting schedules, ISO AMT, ESPP qualifying dispositions, 10b5-1 plans, concentrated stock — the tax side and the investment side are the same decision. We run both so the plan holds together across years, not just this April.

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Sound familiar?

RSUs vested. A check went to taxes. You’re not sure the timing was right.

ISO options are expiring and you’re not sure how many to exercise or when. You have a K-1 from a fund and have no idea how it affects your quarterly estimates. Your CPA files the return. Your advisor manages the portfolio. They’ve never spoken.

These aren’t filing problems — they’re coordination problems. And they’re expensive.

RSU withholding rate often doesn't match your actual tax bracket
ISO exercises and AMT exposure managed as guesses, not a model
Concentrated position with no diversification plan
CPA and financial advisor operating in separate conversations

What this requires

Equity planning only works if it runs across years.

RSUs, ISOs, and concentrated stock are multi-year tax events. A real plan needs to connect the vest schedule, the tax calendar, the investment strategy, and your personal goals across time.

Multi-year planning horizon

We look at vesting schedules 2–5 years out, not just what's happening this April. That means optimizing for the full tax lifecycle of each grant, not just the next filing date.

Real coordination with investment

Tax planning on equity only works if the investment side knows about it. Withholding amounts, exercise decisions, and concentrated positions need to be decided together, not separately.

Actual execution

A plan to harvest losses, optimize exercise timing, or structure 10b5-1 sales only works if you're willing to act on it throughout the year — not just at year-end.

Ready to coordinate? Let’s talk about building a plan that works across the vest calendar. Or start with the owner review to see what else you might be missing.

The equity landscape

Same employer, very different tax mechanics.

Most equity-comp employees hold two or three of these at once. Each has its own tax treatment, its own timing window, and its own interaction with the rest of the year.

RSU

Restricted stock units

Ordinary income at vest. Employers typically withhold at a flat supplemental rate — often below your actual bracket. Under-withholding is the most common RSU surprise on April 15.

ISO

Incentive stock options

No regular income at exercise, but the spread is an AMT preference item. Multi-year planning around the AMT crossover — how many options to exercise and when — is the whole game.

NSO

Non-qualified stock options

Ordinary income on the spread at exercise, with payroll taxes withheld. Less complex than ISOs, but timing and concentration still matter.

ESPP

Employee stock purchase plan

The discount is ordinary income. A §423 plan with a 15% discount and a lookback is one of the best risk-adjusted returns employees can access — if you plan the sale.

Founder / early stock

Founder & early-stage stock

§83(b) elections, QSBS under §1202, and founder share coordination with a later sale. The §1202 exclusion rules are powerful and strict — they run from the original acquisition date.

Concentrated

Concentrated stock positions

When one position is a large share of net worth, the tax side and the portfolio side must be run together. Staged sales, direct indexing, exchange funds, and charitable strategies all apply.

General educational descriptions. The actual treatment of your specific grants depends on the plan documents, grant type, and personal facts. This is not tax or investment advice.

Run the numbers

Model your equity before the decision.

RSU Tax Impact

RSU Tax Impact Calculator

See the gross income recognized at vest, your actual tax vs. what was withheld, and any shortfall requiring a quarterly payment.

Calculate my RSU tax ISO / AMT Exposure

ISO/AMT Exposure Calculator

Model the spread, regular tax, and tentative minimum tax before you exercise — find how many options you can exercise without triggering AMT.

Model my AMT exposure Equity Event Planner

Equity Event Tax Planner

Add all your vests, exercises, and stock sales for the year — see your combined equity tax exposure and what to do before December 31.

Plan my equity events

Educational estimates only. Not tax or investment advice. Individual results will vary.

Concentration risk

When one position is 30%+ of the balance sheet.

The tax cost of selling is only half the conversation. The other half is what happens to the financial plan when a single stock represents a third, half, or more of net worth — especially when the same stock is also the employer’s.

The right answer is almost never “sell everything on April 1” or “never sell.” It’s a multi-year program that uses the taxable-gain budget you have each year, pairs it with lot-level harvesting, and coordinates with charitable and estate moves where those fit.

Tools in the concentrated-stock toolkit

Staged sales sized to the annual tax-bracket budget
10b5-1 plans for insiders to sell through blackout windows
Direct indexing to generate tax losses that offset gains on the concentrated position
Exchange funds for qualifying investors looking to diversify without an immediate sale
Charitable contributions of appreciated stock (donor-advised funds, CRTs) for eligible donors
Estate and gifting strategies that move basis and future appreciation to the right hands

See how tax and wealth coordinate

California layer

California adds a second bracket to every equity decision.

California taxes RSU vests, ISO disqualifying dispositions, and long-term gains at ordinary rates — with no preferential capital-gains rate and a top bracket above 13%. Residency and the timing of the vest both matter. A move across state lines a month too early or too late can change the bill.

RSU sourcing on vest

California generally sources RSU income based on the portion of the vesting period you worked in-state. Relocation mid-cycle requires an allocation, not a clean break.

ISO AMT at the state level

California has its own AMT. The federal AMT crossover planning isn't enough on its own — the CA calculation can change the optimal exercise pattern.

Residency & sourcing audits

California is active on residency and equity-comp sourcing. Documentation of days, domicile ties, and grant-to-vest timing should live alongside the planning.

QSBS treatment in CA

California does not conform to federal §1202 in the same way. Qualifying for the federal exclusion does not guarantee a California outcome. Plan both returns.

How the engagement works

One plan, reviewed every year.

Step 01
Grant inventory
We catalog every grant — type, vesting schedule, strike, grant date, and running cost basis — so planning decisions run off an accurate picture.
Step 02
Multi-year tax model
A 3–5 year model of income, vests, exercises, and projected sales — with bracket, AMT, and state overlays — so you see the tradeoff before you make it.
Step 03
Sale & diversification plan
A written annual plan that lines up sales, exercises, and charitable moves with the broader portfolio through Measured Risk Portfolios.

What changes

What’s different on the other side of working together.

Equity comp mistakes are invisible until they show up on a tax bill. This is what changes when the planning is done before the decision, not after.

No more AMT surprises on ISO exercises

We model the AMT crossover before you exercise — the exact number of options you can exercise without triggering AMT liability. A $40k AMT bill from an unmodeled exercise year is the most common avoidable mistake in equity comp planning.

RSU lot selection and timing, done intentionally

Vesting events are ordinary income — the timing and which lots you sell afterward determine capital gain treatment. Most people sell whatever shares are available. We pick the lots that minimize tax drag across years.

A written plan for the concentrated position

Direct indexing, donor-advised fund, exchange fund, or a staged sale — each has different tax, liquidity, and timing implications. We model all of them against your situation and put a plan on paper before any move is made.

CPA and advisor on the same call, every quarter

Investment decisions and tax decisions are the same decision when equity comp is involved. We run both sides so nothing happens in the portfolio that the tax picture didn't see coming — and vice versa.

Common questions

What owners and executives usually ask first.

How do I actually get my CPA and advisor to coordinate?

Start by asking each one: 'Have you looked at the tax impact of my portfolio decisions this year?' and 'Have you talked to my [CPA/advisor] about my vesting schedule?' If the answer is no, the gap is real. Coordination usually requires someone to own the agenda — which is what we do as part of the engagement.

Won't having them coordinate just cost more?

It typically costs less than the mistakes it prevents. An unplanned ISO exercise that triggers $40k in AMT, or a vesting event that lands in the wrong tax year — those are expensive. Coordination recovers more than it costs for most people with equity comp above $100k in a year.

What if my advisors won't work together?

Some advisors are territorial about coordination. If your CPA or advisor declines to engage with the other side of your picture, that's a signal worth taking seriously. For complex equity situations, siloed advice is a structural problem — not a personality preference.

Can I manage RSUs and options myself without a CPA?

You can track the mechanics yourself. What's harder to DIY is the year-over-year strategy: which year to exercise ISOs to avoid AMT, how to time large vesting events relative to other income, whether to use a 10b5-1 plan, and how your concentrated position affects your overall allocation. Those decisions compound across years.

What about AMT on my ISO options?

AMT exposure from ISOs is one of the most common and most avoidable tax surprises for high-income owners and executives. The math requires running the AMT calculation before you exercise — not after. We model ISO exercise scenarios against your other income sources to find the range that doesn't trigger a large AMT bill.

Is tax-loss harvesting actually worth the effort?

For concentrated positions and high-income years, yes — meaningfully so. It requires proactive portfolio management and CPA coordination, which is why most people don't get it. But for someone with $500k+ in appreciated stock and a large ordinary income year, systematic harvesting can offset tens of thousands in gains.

How often should my CPA and financial advisor actually talk?

At minimum: before year-end to plan around income and portfolio events, and before any major equity transaction. In practice, we find quarterly check-ins work well — one of those aligns with estimated tax due dates, which is a natural coordination point anyway.

Go deeper

Ready to build a plan?

Matt Reese, CPA works with equity-comp employees and executives to build multi-year plans around RSUs, ISOs, NSOs, and concentrated stock — coordinated with the full tax and investment picture.

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Tax services provided through Matt Reese, CPA. This page is educational and does not constitute tax or investment advice.

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