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26 min

Anomaly Angle #1: Strategy vs Tax Filing - What Business Owners Need to Know

The launch episode: the difference between year round strategic planning and filing a return, covering entity structure, wage optimization and ongoing exposure reviews.

Hosts: Greg O'Brien, CPA & John Malone · Anomaly CPA

Summary

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If your accountant only hears from you in March and April, you are buying a filing service, not a tax strategy. In the first episode of The Anomaly Angle, Greg O'Brien and John Malone walk through a real onboarding: a digital security company with three equal owners, strong growth, and a set of missed opportunities that had been sitting in their returns for years.

The diagnosis

The client arrived through their CFO, frustrated that their previous CPA answered every strategy question with "do not bother with those." Three things stood out in the first review: deductions with real nuance were missing, an obvious tax credit was nowhere to be found, and the owners felt broke despite rising profit and had almost nothing set aside for retirement.

Wages versus distributions

The company operated as an S corporation with three owners at a third each. Multi member S corps are rarely ideal, because distributions must be strictly proportionate to ownership, but after ten to twelve years of operating it was not worth unwinding.

The bigger issue was that all of the profit, roughly 700,000 to 800,000 dollars across the three owners, was coming out as wages. That is not wrong, it just removes the reason to be an S corporation at all: distributions are not subject to FICA and Medicare, wages are. A reasonable compensation study set a defensible wage for the following year and moved the rest to distributions, saving each owner around 10,000 to 12,000 dollars a year.

The QBI classification error

The Qualified Business Income deduction from the 2017 Tax Cuts and Jobs Act gives pass through owners up to 20 percent off the top, with phase outs above certain income levels. All three owners were showing zero QBI deduction despite having wages and income.

The cause was classification. The prior accountant had filed them as a specified service trade or business, which killed the deduction. In practice the company built its own AI and software to serve customers, a heavy technology component that does not belong in the services bucket. A QBI study confirmed it, and amended returns within the statute of limitations are bringing back roughly 25,000 to 30,000 dollars per owner, about 75,000 dollars in cash.

The pass through entity election

All three owners live in high tax East Coast states and were well past the SALT cap. Around 36 states now allow a pass through entity election, which pays the state tax at the business level and turns a capped personal deduction into a business deduction. Same money, different pocket, legally. They had never heard of it. The saving runs into five figures each over several years.

The R&D credit nobody claimed

A company writing its own proprietary AI and software is a natural candidate for the Section 41 research credit. A pre qualification questionnaire and a sample of contracts, methodology and project records confirmed there was qualifying activity, and multi year amendments are recovering close to six figures in missed credits, with more available going forward.

The common objection is "we are not scientists." The test does not require that. The work has to rely on one of the hard sciences, and computer science counts. It also does not have to be new to the world, only new to the business. A restaurant redesigning how its drive through works can qualify.

The balance sheet nobody read

Once the bookkeeping came in house, the team found an asset that should have been written off years earlier and had been sitting on the balance sheet since a bad journal entry. Fixing it released the expense. As the firm puts it internally: if you want to find where the bodies are buried in a business, look at the balance sheet.

How the process actually runs

New clients go through a deep dive covering the business, the real estate, and the family situation, and come out with five to seven levers to pull and a plan to execute each one. The accounting side runs in parallel, fixing errors or building the books from scratch, because nobody can plan on numbers they do not trust. That foundation is set in the first 30 to 45 days, then implementation starts.

After that it is a rhythm: scheduled meetings through the year, projections, estimated payments, and unlimited communication on a fixed fee, so nobody avoids a question because they fear the invoice. Laws change, businesses change, and an offer to sell can arrive tomorrow. The tax return is only a report card on how well the year was planned.

Key takeaways
Key takeaways rich text
  • Taking every dollar out of an S corp as wages removes the point of the election, a reasonable compensation study moved 10,000 to 12,000 dollars a year back to each owner
  • A wrong SSTB classification had zeroed out their QBI deduction, amended returns are refunding about 75,000 dollars across three owners
  • The pass through entity election turns capped state taxes into a business deduction in roughly 36 states
  • The R&D credit does not require scientists or a world first, only work that is new to the business and grounded in one of the sciences
  • Errors hide on the balance sheet, and a preparer who only sees it in January will not find them

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