Business tax planning for $3M-$50M service businesses

Filing isn’t planning.By April, your tax year is already over.

A return can only report what happened. We plan your business and personal taxes every quarter, from the books we close each month, then file both returns. Led by Barry Roach Jr., EA.

“All he was doing was just filing my returns.”“They call me once a year and that’s it.”“I was blindsided, honestly.”Said to us on real calls. Names left out, words left in.

2 minutes. If it’s a fit, you pick a time with Barry. No obligation.

What does business tax planning look like for a $3M+ company?

It means working from your actual numbers every quarter and making the calls before the year closes. That covers owner salary, distributions, estimated payments, and the tax effect of hires and big purchases. At Core, an Enrolled Agent does it on the team that closes your books by the 15th, and both business and personal returns are included.

Why do I owe so much in taxes? Usually one of four reasons.

Each of these can be seen coming months ahead... if somebody’s watching.

1. Your salary was set years ago

If your salary was set when the business was half its size, it’s probably wrong now. Too low invites IRS questions. Too high is payroll tax you didn’t need to pay.

2. Your estimates are based on last year

Safe-harbor payments keep you out of underpayment penalties. In a growing company, they can still leave a big balance due in April. We recalculate your estimates every quarter from actual numbers, so they track what you’ll actually owe.

3. Big decisions happened without the tax answer

A distribution, new equipment, buying out a co-owner, a second location. Each one has a tax effect that’s easy to plan and hard to fix afterward. We run the tax side before you sign.

4. The strategy sounded great at a conference

Some of the big “tax savings” you hear about are timing tricks that come back later, often when you sell. If you couldn’t defend it in an audit without sweating, we won’t recommend it.

“I want to be able to defend what I’m doing if I’m audited.” Said to us on real calls. Names left out, words left in.

Your own salary is the biggest tax decision you make each year

If you own an S-Corp, the IRS expects you to pay yourself reasonable compensation. That’s just the salary it would cost to hire someone to do your job. What’s left can come out as distributions, without payroll tax.

We set that number for every owner, document how we got there, and revisit it when the business changes. That one number drives your payroll tax, your distributions and how the IRS reads your return. It shouldn’t be a guess.

An $8M company, a $3.6 million salary, and a question nobody asked

In June 2024, I sat down with the owner of an $8M company and his daughter. The company was a C Corporation, and the owner paid himself a $3.6 million salary. I asked if anyone had ever discussed an S Corporation election.

They looked at each other. “Nope. Never heard of it.”

They went with a firm that was a bit cheaper, maybe $300 a month. By December, their return was due January 15th and still wasn’t done. They called back.

The next summer, I modeled the options. An S Corporation election with a lower salary came out more than $100,000 lower in tax. Saving $300 a month had pushed that conversation back a full year.

Nobody had asked the question, because it was nobody’s job.

Growing profit compounds. A one-time tax trick doesn’t.

A deduction you stretch for saves money once, if it holds up. Profit you keep growing raises what your company is worth every year after.

So the tax plan works for the growth plan... not the other way around. And we’ll tell you straight when a tax move would cost you more than it saves.

Bigger strategies for high-income owners, with the year-two math on the same page

Once the business throws off real profit, the options get bigger. A retirement plan sized to your profit instead of a standard 401(k). Cost segregation on a building you own. A second entity. An accountable plan, so the business repays you tax-free for costs you cover personally.

Each can save real money. Each also has a second year. Depreciation taken now can come back as tax when you sell. Some retirement plans commit you to a contribution in a slow year too.

We put both numbers in front of you before you decide... what it saves now and what it costs later. If the second number is bigger, you’ll hear that from us first.

Planned every quarter, from books closed by the 15th

  • Quarterly tax planning for the business and every owner
  • Estimated payments recalculated each quarter from actual year-to-date numbers
  • The business return and the owners’ personal returns, prepared and filed
  • Reasonable compensation set and documented for each owner
  • The tax effect of big decisions run before you commit
  • Year-end planning before December 31, while there’s still time to act
  • IRS notices handled, with Enrolled Agent representation. State notices answered too.

The person planning your taxes can also answer the IRS

Your tax plan uses this month’s books, closed by the same team. Nobody waits for you to send a spreadsheet in March, and nobody plans from last year’s return.

The work is led by Barry, an Enrolled Agent. That’s a tax license issued by the IRS itself, so the person who plans your taxes can also answer the IRS if it writes.

What we won’t do, and what’s quoted separately

No aggressive schemes, no offshore structures, nothing that needs a “well, technically” to explain. You get every deduction you’re entitled to, a structure that fits the business, and timing that’s planned.

Pricing covers one operating entity plus the owners’ personal returns. Extra entities or multi-state payroll are quoted on the fit call, before you sign.

Questions

What owners ask about their taxes before the fit call

How much should I pay myself from my S corp?

A reasonable salary for the work you actually do. The test is what it would cost to hire someone else to do it, and the number should be documented so it holds up. Too low invites IRS questions. Too high is payroll tax you didn’t need to pay. At Core, an Enrolled Agent sets the number for each owner and revisits it when the business changes.

Why do I owe so much in taxes this year?

Usually one of four things. Your salary was set years ago. Income grew but your estimated payments were based on last year. A big decision happened before anyone ran the tax side. Or a strategy that sounded great turned out to be a timing trick. At Core, quarterly planning from books closed by the 15th is built to catch all four while there’s still time to act.

What tax strategies make sense for a high-income business owner?

The ones that still make sense in year two. It starts with the basics done right: your salary, your entity structure and estimated payments that track actual income. Then come the bigger moves, like a retirement plan sized to profit or cost segregation on property you own. At Core, an Enrolled Agent shows you this year’s savings and the later cost side by side before you commit.

Are my personal returns included?

Yes. The owners’ personal returns are included along with the business return. Core’s pricing assumes one operating entity plus the owners’ personal returns, from $5,000 a month for $3M-$10M companies. Extra entities or multi-state payroll are quoted on the fit call before you sign, so you know the full number up front.

Can I switch tax preparers in the middle of the year?

Yes. Planning runs from your current books, so it can start in any quarter. If a return is already in progress with your current preparer, it can usually be finished there, and the next returns move to Core. We coordinate the handoff either way, so nothing falls between the two firms.

When are estimated taxes due?

Federal estimated payments for individuals are due four times a year: April 15, June 15, September 15 and January 15 of the following year. If a date falls on a weekend or holiday, it moves to the next business day. At Core, we recalculate the amount before each one from your actual year-to-date numbers.

Enrolled Agent vs. CPA: who should plan my taxes?

Either can, if they actually plan. Both can prepare returns and represent you before the IRS. A CPA is licensed by a state and also does audit and attest work. An Enrolled Agent is licensed by the IRS, and the credential is tax only. What matters more is whether anyone plans before December 31. At Core, an EA plans every quarter and files both returns.

April shouldn’t be a surprise.

You’ve got three honest options. Leave it as it is. Build the finance team yourself. Or hand all four jobs to one team.

If your tax picture looked exactly like this six months from now, would that be okay? If not, tell us your revenue and what decisions are coming. On a 30-minute call with Barry, you’ll know whether we fit.

See if we’re a fit →

2 minutes. If it’s a fit, you pick a time with Barry. No obligation.