For owner-operators

Business owner tax planning, built to run year-round.

The tax return tells you what already happened. Planning decides what the next one looks like. We run both — entity structure, owner comp, quarterly estimates, year-end moves, and the coordination with the long-term portfolio that most owners never get.

Check your setup Talk with Matt

What’s included

Entity structure
Owner comp
Quarterly rhythm
Year-end moves

Sound familiar?

The business is doing well. Tax time is still a scramble every year.

Most owners have a CPA who shows up in March. By then, the decisions that would have mattered — the bonus, the retirement contribution, the equipment purchase — are already made. You sign a return you don’t fully understand and write a check you didn’t plan for.

We run the calendar differently. In October, we call you with a number. You still have time to do something about it.

CPA only shows up at filing time — nothing proactive
Quarterly estimates feel like guesses, not a plan
S-corp salary hasn't been reviewed in years
Business and personal returns handled separately, no coordination

What this actually takes

Tax planning only works if you’re ready to plan.

This isn’t a tax prep service that files what already happened. It’s a quarterly planning partnership that changes what happens next. That requires three things.

Real engagement

Quarterly check-ins aren't optional. They're where decisions get made — in October, not March. You'll spend 2–3 hours per quarter on planning conversations.

Current financials

We work from real YTD numbers, not estimates. That means your books need to be reasonably current — not perfect, but actual income and actual expenses tracked.

Openness to change

If we recommend adjusting your S-corp salary, restructuring retirement, or shifting distributions, you need to be willing to act. Tax planning is only valuable if the plan actually gets executed.

Right for you? Take the owner review — it takes 5 minutes and shows where you actually are. If you find out you’re not ready yet, we have the S-corp salary calculator, quarterly estimate planner, and year-end tax planner are free.

The gap

A tax preparer files. A tax plan changes the number.

Most owners have someone who files a return once a year. Far fewer have someone who owns the rhythm of decisions that shape the return before it’s filed — the entity, the comp, the estimates, the retirement plan, the allocation at year-end.

Entity and S-corp comp

The single biggest recurring lever for most owner-operators. We build a defensible reasonable compensation analysis and re-run it as the business grows.

Quarterly estimates

Safe-harbor vs projection-based estimates, coordinated with distributions so cash actually matches what the IRS and FTB expect.

Retirement plan architecture

Solo 401(k), SEP, SIMPLE, or a cash balance / defined benefit layer — matched to profit, age, and staff. This is where high-earning owners shelter the most.

Year-end moves

QBI optimization, depreciation elections, accountable plans, PTET, and the timing of major expenses or distributions — run before December, not in April.

What’s inside

The pieces of a business owner tax plan.

Entity structure review

Sole prop, LLC, S-corp, partnership, or C-corp — we review the current election against your revenue, number of owners, exit plans, and state exposure, and flag when a change actually pays back.

S-corp tax planning

Owner compensation & payroll

Reasonable compensation built on industry data, owner duties, and revenue. Documented so the decision holds up — and re-examined as the business scales.

How we set S-corp comp

Quarterly planning cadence

A real check-in every quarter, tied to current-year books. Estimates adjusted, entity decisions revisited, and a short list of moves for the next 90 days.

Year-end planning

Wealth coordination

Distributions coordinated with the long-term portfolio, retirement plan design, and concentration from the business itself — through Measured Risk Portfolios.

Tax & wealth planning

Equity comp coordination

RSUs, ISOs, NSOs, ESPP, and concentrated founder stock — multi-year planning that sits alongside the business and not in isolation.

RSU & equity comp

Exit & liquidity planning

When a sale or partner buyout is actually on the table, we run the pre-LOI structure, the sale mechanics, and the post-close reinvestment plan.

Selling a business

Running an S-Corp?

See how salary, distributions, and QBI interact — and what a defensible reasonable comp analysis actually looks like.

S-Corp salary, distributions, and QBI

The rhythm

A quarterly cadence, not a March scramble.

Tax planning has real windows. Miss them and the decision is already made. This is what an owner’s year looks like when someone owns the calendar.

Prior-year return and extension call. Entity and owner-comp decision set for the year.

Mid-year projection and estimate check. Retirement plan funding plan confirmed.

Fall planning window — QBI, depreciation, entity elections, and PTET considerations.

Year-end moves locked in before December 31, including distribution and comp trueups.

The bigger picture

Tax and wealth, handled together.

A strong tax plan keeps the business efficient year to year. But the real compounding happens when distributions and owner income are converted into an investable balance sheet — and when the portfolio is coordinated with the entity, the concentration, and the tax picture.

See the wealth side

Retirement plan design that matches profit and owner age
Distribution timing coordinated with portfolio cash needs
Concentration management for owners heavy in one business or one stock
Estate, trust, and succession coordination as wealth grows

What changes

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

Not a list of services — a list of what actually stops happening and starts happening.

An October call instead of an April surprise

We reach out before year-end while there's still time to act — a bonus, a retirement contribution, equipment, the right distribution timing. The decisions that actually change the return get made with the books open, not after they're closed.

S-corp salary reviewed and documented

Reasonable comp re-examined every year as the business grows. Defensible number on file. The single most common IRS audit trigger for S-corp owners — eliminated.

Quarterly estimates based on what you actually earned

Real YTD numbers, not last year's safe harbor. No underpayment penalty. No writing a check in April that you didn't plan for.

Business and personal returns treated as one picture

The 1120-S and the 1040 are the same decision, run by the same team. No mismatches, no K-1 surprises, no missed deductions from two people who never talked.

Common questions

What owners usually ask first.

How much time does proactive tax planning actually take?

An October planning call runs about an hour. Quarterly estimate check-ins are 15–20 minutes each. Year-end is another hour. In a typical year you're looking at 4–5 hours on your end — compared to the scramble most owners put in every March.

Will this actually lower my tax bill?

For most profitable S-corps and owner-operated businesses, yes — usually meaningfully. The biggest levers are retirement plan contributions, reasonable comp calibration, entity structure, and timing. Owners who haven't had proactive planning often have meaningful annual savings sitting unclaimed.

I already have a CPA. What would change?

If your CPA contacts you proactively, reviews your salary and estimates before year-end, and coordinates with your financial advisor — you may already have what you need. If they primarily show up in March with a return to sign, that's the gap. We work on the tax picture year-round, not just at filing.

What if my CPA pushes back on proactive planning?

Some CPAs prefer reactive work — it's a simpler model to run. If your CPA isn't interested in mid-year planning calls, it's worth asking whether the relationship is still the right fit. We're built around owner-operators who want a plan before the bill arrives.

What if I'm starting mid-year — is it too late?

No. The most valuable moves — adjusting your W-2, accelerating deductions, setting up a retirement plan — are available any time before December 31. Starting in October still leaves time to make a real difference in the current year.

Do I need to be an S-corp to work with you?

No. We work with sole proprietors, single-member LLCs, partnerships, and C-corps too. Entity structure is one of the first things we look at — if a different setup would save you money, we'll say so.

Reviews

What clients say.

“Matt is the best! Does a great job at explaining everything and answering all your questions. As a small business owner I trust Matt to handle my taxes and provide suggestions based on my business.”

Victoria G.

Small business owner · Google

“I'm a startup and it took me several months to find the right CPA. Matt is such an asset — a wealth of knowledge, passionate, straight-shooter, proactive, humble and kind-hearted. No need to look any further.”

MJ's Eatery

Startup, San Diego · Yelp

“We had to amend a few returns when a mortgage underwriter found a small error. Matt replied right away and made himself available on a Friday night to alleviate our concerns. Pay the money to have a CPA do it right the first time. Highly recommended.”

Justin A.

San Diego, CA · Yelp

Go deeper

Ready to build a plan?

Matt Reese, CPA works with business owners on the full tax plan — entity structure, reasonable comp, quarterly rhythm, and year-end moves — coordinated with the long-term portfolio.

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

Monthly tax planning reminders

One email per month — what’s due, what to do, and which tool to use. No fluff.