Keep more of what
you have built.
Tax preparation looks back at a year that is already over. I look forward: I read your returns and your business K-1s, show you what is driving your bill, and plan your pay, your income, and eventually your exit, so the tax you pay reflects choices you made on purpose.
A return looks back. A plan looks ahead.
Reports the past
A return records what already happened. By the time it is filed, the year is closed and most of the decisions that drove the bill can no longer be changed.
Shapes the future
I work ahead of the year, deciding which accounts to draw from, how much to convert, and when to realize income, so the bill reflects choices you made on purpose.
From last year's return to next year's decisions
Tax planning starts with the real numbers, not a questionnaire. I read your actual returns, several years at a time, and your investment accounts down to the cost of each holding, so the picture reflects what is really driving your bill, including what is already working in your favor.
Then I explain it in plain English and model the options, always with the math shown. I do not prepare your return; I work alongside your CPA, who files it, so the plan and the return agree.
- 01Read
- 02Explain
- 03Model
- 04Choose
- 05Deliver
Revisited every year, and whenever something changes. Point at a step to see what happens in it.
Tax planning for every stage of ownership
The moves that matter change as your business grows, sells, and turns into the money you live on. I plan for the stage you are in and set up the one coming next.
Pay yourself and the IRS on purpose
Entity choice, reasonable salary, the QBI deduction, and retirement plans that move six figures of income off this year's return.
Structure the sale before you sign
Asset or stock, how the price is allocated, when the gain lands, and which planning has to happen before a deal is in motion.
Turn a liquidity event into lifetime efficiency
Filling brackets, Roth conversions, withdrawal order, Medicare lines, and giving, planned across many years at once.
Set your salary so the business works for you
If your business is taxed as an S corporation, how you split money between salary and distributions changes your tax bill. Salary carries payroll tax; distributions do not. The IRS requires a reasonable salary for the work you do, so the goal is not the lowest number possible. It is the right number, documented and defensible.
I review your entity, your pay, and your distributions together with your CPA, because the same salary decision also affects your QBI deduction and how much you can put into a retirement plan.
- GoalThe right number, documented and defensible
- Also movesYour QBI deduction and retirement plan room
- Reviewed withYour CPA
Not the lowest salary possible. The right one.
Protect the deduction owners rely on
The qualified business income deduction can take up to 20% of your business income off your taxable income. Above certain income levels it starts to shrink, especially for professional service businesses, and it can be capped by the wages your business pays.
I track where you sit against those lines each year, and I plan salary, retirement contributions, and the timing of income so you keep as much of the deduction as the rules allow.
Checked every year against where you sit.
Use your business to save more than a 401(k) allows
A business gives you retirement plan options most employees never get. A 401(k) with profit sharing (a solo 401(k) if you have no employees), with a cash balance plan layered on top, can let a high-earning owner set aside far more each year than a standard 401(k) allows, and every dollar contributed comes off this year's taxable income.
I model which design fits your income, your age, and your employees, then coordinate it with the plan provider and your CPA.
Every dollar contributed comes off this year's taxable income.
Plan around the years that do not look alike
Owner income rarely arrives in a straight line. A big year, a slow year, or a large distribution can each change your bracket, your estimated payments, and which planning moves make sense.
I keep your estimated payments on track to avoid penalties, and I look for chances to shift bonuses, distributions, or deductions between years so a spike in one year does not cost more than it has to. For owners still building, I also coordinate backdoor and mega backdoor Roth contributions, health savings accounts, and 529 plans so the accounts work together.
Point at a year to see how it is planned.
The structure of your sale sets the tax on it
Whether a buyer purchases your company's assets or its stock, and how the price is divided among equipment, goodwill, a noncompete, and consulting, can change the tax you owe by a wide margin. Some of that price may be taxed at capital gains rates and some at ordinary income rates.
I model the structures on the table and the allocation the buyer proposes, so you and your attorney negotiate knowing what each version leaves you after tax.
Some of the price may be taxed at capital gains rates and some at ordinary income rates.
Decide when the gain lands
A sale does not have to put all of its gain into one year. An installment sale can spread it across several, and the year you close can be planned around your other income. If your company qualifies as small business stock under Section 1202, much or all of the gain may be excluded entirely, but the requirements are strict and need to be checked well before a sale.
A large gain also reaches beyond income tax. It can add the 3.8% investment tax and raise Medicare premiums two years later, so I plan the sale year and the years around it together.
The year you close can be planned around your other income.
Some planning only works before a deal is in motion
Several of the most valuable moves have a deadline that arrives before closing. Giving shares to a donor-advised fund or charitable trust can avoid tax on that portion of the gain, but only if the gift happens before a sale is substantially certain. A change of residence to a state with lower or no income tax can matter too, though states look closely at moves made right before a sale.
This is why I want to start well ahead of an exit. My Certified Exit Planning Advisor training is built around exactly this window.
- Section 1202 checkwell before a sale
- Change of residencewell ahead
- Charitable gifts of sharesbefore a sale is substantially certain
- Deal in motionthe window starts closing
- Closing
Several of the most valuable moves have a deadline that arrives before closing.
Turn a liquidity event into lifetime tax efficiency
Once the business becomes money you live on, the work shifts to managing income across many years at once.
Income managed across many years at once.
Six levers I use after the sale and beyond
Most tax savings do not come from a single move. Some of these I decide once a year, others run quietly in the background all year, and they work best when each one is aware of the rest.
Filling the low brackets
I fill the lower brackets on purpose and leave income on the table only when the next dollar would cost too much.
Roth conversions
I plan conversions across several years, moving money to tax-free ground while your rate is low and before withdrawals are forced.
The right withdrawal order
I decide which account funds each year of spending, down to the account level, so the order you draw on works in your favor.
Cliffs and phase-outs
I watch the income lines that raise Medicare premiums, add the 3.8% investment tax, shrink the owner's QBI deduction, or phase out credits, and plan around them.
Tax-smart investing
I harvest losses as markets move, rebalance with the tax bill in mind, and, where available, manage gains stock by stock.
Charitable deductions
I compare the standard deduction with itemizing, group gifts into the right years, and use tools like donor-advised funds and gifts straight from your IRA.
Use your low-tax years when they come
Tax brackets work like a staircase, not one flat rate. Low-tax years show up at different points: a slow year in the business, the years after a sale, or the gap between stopping work and required withdrawals. I treat those years as room to use, taking some income while it is taxed lightly instead of letting it pile up and get taxed at a higher rate later.
The goal is a steadier tax rate over your whole life. I would rather you pay a moderate rate across many years than a low rate now and a steep one later, once withdrawals and Social Security stack on top of each other. Staying in a low bracket can also drop the tax on long-term investment gains and dividends to zero, so the same room does double duty.
Brackets work like a staircase, not one flat rate.
Move money to tax-free ground
A Roth conversion means paying tax on some retirement money now, so it and all its future growth come out tax-free later. Done well, it uses up the low-taxed room in your bracket each year without tipping into the next one, and it shrinks the pre-tax balance that would otherwise force large required withdrawals later on.
How much to convert is a decision I make with you each year, not a one-time bet. I look at several years at once, so the conversions you make today account for the Social Security, withdrawals, and Medicare premium limits coming tomorrow.
- Tax due on conversion$17,280
- Future tax avoided on growth$41,500
- Years modeled together7
Illustrative figures for example only.
Draw from the right account in the right order
Your money usually sits in three kinds of accounts: regular taxable accounts, pre-tax accounts like traditional IRAs, and tax-free Roth accounts. The usual rule of thumb for which to spend first is not always best. By choosing the source of each year's spending on purpose, I can keep your taxable income low in some years and use it deliberately in others.
The order also protects what you pass on. Drawing from pre-tax accounts at a low rate today can spare your heirs from inheriting an account that taxes them at a high one.
Choosing the source of each year's spending on purpose.
Stay under the lines that cost you most
Once you are on Medicare, income above certain lines raises your premiums, and the increase applies to the whole year. It works like a cliff: a single dollar over the line can cost far more than that dollar, and the rules look back two years, so today's income can raise a premium two years from now.
Medicare is one of several lines like this. Others add the 3.8% net investment income tax, shrink the qualified business income deduction owners rely on, phase out credits, or make more of your Social Security taxable. I keep all of them in view when I plan conversions and time income, so a move that looks smart on paper does not quietly cost more than it saves.
The rules look back two years, so today's income can raise a premium two years from now.
Keep your investments working on taxes all year
Capturing tax losses is not a once-a-year event. As markets move, I look for losses to offset gains now and bank the rest against gains later. When your investments drift off target, I factor in the tax before rebalancing, so getting back on track does not hand you an avoidable bill.
Where available, holding an index as its individual stocks instead of one fund lets me manage gains and losses stock by stock, and leave out companies you would rather not own, without giving up the tax savings.
- Rebalancingtax-aware
- Realized tax impact, tracked-$8,100
Illustrative figures for example only.
Make your generosity work twice
When giving is part of your life, how you give changes the tax result. Grouping several years of gifts into one year can lift you over the standard deduction when it counts. A donor-advised fund, which is a simple charitable account, lets you take the deduction now and give the money out over time. And donating stock that has grown in value, instead of cash, skips the tax on that growth entirely.
From age 70½, you can send money straight from your IRA to a charity, called a qualified charitable distribution. The gift is not added to your taxable income, and once your required withdrawals begin, it counts toward them.
Grouping gifts can lift you over the standard deduction when it counts.
A plan you can act on, and the reasoning behind it.
What is in yours depends on your return and your year. Every recommendation comes with the figures it rests on, so you can see why it is worth doing and what it assumes.
- A written tax plan for the year ahead
- A visual summary of your brackets, gains, deductions, and flagged opportunities
- The assumptions and the math behind each recommendation
- The moves worth making, in priority order
- Coordination with your CPA and, during a sale, your attorney
- A spring review of your return, a summer check against the plan, and year-end planning in the fall
- A fresh look whenever the law, your business, or your income changes
See what a forward-looking plan saves you.
I will look at your returns, your accounts, and the years ahead, then show you the moves worth making, with the math behind each one, while there is still time to make them.
Schedule an Exploration CallKeep Reading
From the blog
How to Document a Reasonable S-Corp Salary for an Audit
Build a dated file before you pay yourself. It holds your duties and weekly hours, saved wage data for comparable roles in your metro, the specific salary you chose and why, and a signed approval, all backed by matching payroll records.
Read MoreWhat Makes an Advisor Modern When You Own a Business
For a business owner, a modern advisor coordinates with your CPA, attorney, and M&A advisor and keeps your personal plan aligned through a sale. The app is optional.
Read MoreS Corp Paycheck Calculator: How Owners Estimate Salary, Taxes and Take Home Pay
To estimate an S corp paycheck, set a reasonable salary for the work you do, divide by your pay periods, subtract pre-tax deductions and withheld taxes, and treat leftover profit as distributions.
Read More