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Insights  |  Tax Architecture

The Quiet Tax Move Operators
Leave on the Table Every Year

Most founders hand their CPA a shoebox and call it planning.

Chelsea Missick  •  June 29, 2026  •  7 min read

There is a gap between a business owner who pays taxes and a business owner who plans around them. That gap is measured in hundreds of thousands of dollars over the life of a business. And it widens every year.

The move most operators miss is not exotic. It is not aggressive. It does not require a complex trust structure or an offshore account. It is a cost segregation study, executed at the right time, coordinated with the right entity structure.

And most operators who could benefit from it have never had the conversation.


What Cost Segregation Actually Is

When you buy or build a commercial property, the IRS lets you depreciate it over 27.5 years (residential) or 39 years (commercial). That depreciation reduces your taxable income. Slowly.

A cost segregation study is an engineering analysis that reclassifies components of that property into shorter depreciation categories. Carpeting, specialized wiring, certain plumbing, lighting systems, landscaping, these are not 39-year assets. Many qualify for 5-, 7-, or 15-year schedules. Some qualify for immediate expensing.

The result: a significant portion of your depreciation schedule moves from 39 years to right now.

For a $3 million commercial property, a cost segregation study can accelerate $500,000 to $1 million in depreciation into the first few years. At a 37% effective rate, that is $185,000 to $370,000 in tax that stays in your business rather than leaving it.


Why It Works Even Better Now

The One Big Beautiful Bill Act, signed into law and effective from its retroactive date of January 19, 2025, made 100% bonus depreciation permanent. This is the provision that allows assets in the 5, 7, and 15-year categories to be fully expensed in the year they are placed in service.

Previously, bonus depreciation was phasing down. The planning calculus was complicated by timing uncertainty. Now it is permanent.

That changes the math significantly. A cost segregation study in the prior environment might have accelerated depreciation into the next few years. In the current environment, that same study can produce a significant deduction in a single tax year.

For high-income operators, this is not a planning nicety. It is one of the most powerful tools in the code.


The Coordination Problem

Here is what most operators miss: a cost segregation study is not a standalone transaction.

Its value depends entirely on what surrounds it.

If your entity structure does not allow you to use passive losses against ordinary income, the deduction sits in a bucket you cannot touch. It carries forward. It is not worthless, but it is far less valuable than it should be.

If your income is not high enough in the year you take the study, you are accelerating deductions into a low-rate year and potentially pushing income into a higher-rate year later. That is not planning. That is the inverse of planning.

If you are planning to sell the property in three to five years, the depreciation recapture conversation has to happen now. Cost segregation can still make sense, but the analysis is different.

This is why the move gets left on the table. Not because operators do not have eligible properties. Because no one is running the full board.

Your CPA looks at the return. Your engineer runs the study. No one coordinates the two in the context of your entity structure, your income profile, your multi-year tax position, and your eventual exit.

That coordination is the work.


Who Should Be Running This Analysis

You should be having this conversation if any of the following apply:

You own or recently purchased commercial real estate, industrial property, or a building used in your business. You have placed significant tenant improvements or leasehold improvements. You are a real estate operator, syndicator, or investor with an active portfolio. You are running a high-margin business with significant owner income, $500K or above, and your tax liability has been growing faster than your planning has.

The study cost varies by property size and complexity. For a $2 million property, expect $3,000 to $8,000. The ROI on that is typically not close.

The more important number is the cost of not doing it. Every year you own an eligible property without a study is a year you are effectively lending the IRS money at zero percent interest and calling it a strategy.


The Honest Version

I work with Engineered Tax Services for the technical engineering on cost segregation studies. They are specialists. The depth of that analysis matters, this is not something to run through a generalist.

What I bring is the coordination layer. Making sure the study is timed correctly relative to your income. Making sure your entity structure can use the deduction. Making sure the bonus depreciation election fits your multi-year picture. Making sure the eventual exit plan does not create a recapture problem you did not see coming.

The best tax moves are not complicated in isolation. They are complicated in context. A cost segregation study is a good example: simple to understand, significant in value, and easy to get wrong without someone holding the whole board.

If you own eligible property and you have not had this conversation, the conversation is overdue.

Chelsea Missick is the founder of Elevated Business Advisors. EBA works with a maximum of five clients at a time, founders, operators, and investors who want integrated strategy rather than isolated tactics. Apply at elevatedba.com.
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