Tax advisory for business owners: Tax strategy that actually saves you money.
Most owners overpay for one reason: nobody ever walked them through the moves. I set the foundation first, entity structure, owner pay, retirement, timing, and then layer on the strategies most owners have never had put in front of them.
What planning is worth
Your tax bill is a number you can change.
Tax advisory is the planning side of tax work. It decides how you are structured, how you pay yourself, what you put away for retirement, and when you buy the things you were going to buy anyway. Those decisions set the size of the bill long before a return is ever filed.
The payoff is money that stays in the business. Profit you keep is profit you can put into equipment, into people, or into your own retirement instead of sending it to the IRS. And the more your profit grows, the more each one of those decisions is worth.
The second payoff is quieter and owners tell me it matters just as much: you stop being surprised. You know roughly what April looks like by the middle of the year, because the number came from your own books while there was still time to do something about it.
Grounded in the statute
Foundations first. Then we layer.
No gray-area schemes. Every strategy I use is grounded in the tax code and documented so it holds up. But the order matters as much as the list does. The foundation decides how much the advanced work is even worth, so that is where we start.
The foundation
Entity structure and owner pay.
Whether the S-Corp election fits, and how salary versus distributions should be set. That single split moves payroll tax, retirement room, and the QBI deduction at the same time.
Paying your family, correctly.
Hiring your children or your spouse can be a legitimate, documented strategy. Done right, the payroll is real, the work is real, and the savings compound into Roth accounts.
Write-offs done right.
Accountable plan reimbursements, the home office, the business vehicle, travel and meals. The everyday deductions most owners either miss entirely or take in a way that would not survive a second look.
Retirement stacking.
Solo 401(k), SEP, defined benefit. Retirement plans are the biggest lever most owners never fully pull. The right stack turns tax you were going to pay into wealth you keep.
Timing and depreciation.
Section 179, bonus depreciation, and the timing of income and purchases. The calendar is a tax tool: the same equipment bought in December versus January can mean a very different bill.
Estimates without surprises.
Quarterly estimated payments sized from your actual year-to-date numbers, adjusted as the year moves, so the amount due in April is a number you already knew.
Once the foundation is set
What we layer on top.
This is the work most owners have never had put in front of them, because it only pays once the foundation underneath it is right. Each of these is a real position in the code with real requirements attached.
- Short-term rentals
- A property you materially participate in does not have to behave like a rental on your return at all. The rules are specific and the hours are real. Most owners who would qualify never find out that they do.
- Real estate professional status
- Meet the tests and the wall between your rental losses and the rest of your income can come down. The tests are strict and the documentation is the whole game, so it is worth knowing early whether you are anywhere close.
- Self-rentals
- If your business pays rent for a building you own, then who owns it, how the lease reads, and whether the activities are grouped decide whether that arrangement works for you or quietly against you.
- The Augusta rule
- Your company can rent your home for a limited number of days a year without that rent landing on your personal return. Modest on its own. It stops being modest when it runs every year and the documentation is right.
- Oil and gas working interests
- One of the few places the code still allows an active deduction against ordinary income. It carries real risk, it is genuinely not for everyone, and I will tell you plainly when it is not for you.
Which of these you can actually use comes down to your numbers and how you spend your time. Two owners with identical revenue often get completely different answers. Working out which ones are on the table for you is the conversation.
The order of operations
How a tax plan comes together.
Good tax planning is not about finding one deduction or implementing the strategy that happens to be popular this year. It starts with getting the foundation right, then layering additional strategies on top as the business grows.
1. Start with the right business structure.
First, I look at how the business is currently structured. Are you operating as a Schedule C? A partnership? An S corporation? A C corporation? Does the structure still make sense based on your current income, or are you simply operating the same way you were when the business was much smaller?
The goal is not just to determine the best structure for this year's tax return. The structure has to support where the business is going over the next several years, including growth, additional owners, investments, retirement planning, succession, and eventually an exit. Your entity structure becomes the foundation for almost every strategy that follows.
2. Establish compensation and distributions correctly.
Once the structure is right, I determine how money should move from the business to you. For an S corporation owner, that means establishing defensible reasonable compensation and understanding the relationship between wages and distributions.
The goal is not simply to minimize payroll taxes. It is to properly balance FICA taxes, retirement contributions, deductions, cash flow, and compliance so the compensation strategy works as part of the overall plan. I cover the pieces in my guide to the S-Corp owner compensation stack and the election itself in my Florida S-Corp guide.
3. Capture the fundamental strategies first.
Before looking for complicated strategies, I make sure the fundamentals are actually being used correctly. That may include opportunities such as:
- Home office deductions
- Business mileage and vehicle expenses
- Accountable plans
- The Augusta Rule when applicable
- Employing family members for legitimate work
- Retirement contributions
- Health insurance and benefit planning
- Proper reimbursement of business expenses
- Family or advisory meetings when there is a legitimate business purpose
These strategies may sound simple, but when they are properly structured, documented, and consistently implemented, they can produce meaningful savings year after year.
4. Look beyond taxes to the entire financial picture.
Tax strategy should not exist in isolation. I look at how much cash the business is generating, what debt exists, what the business is spending money on, how much the owner is saving, and where those savings are ultimately going.
Sometimes the best opportunity is a tax deduction. Other times it is reducing unnecessary business expenses, restructuring debt, improving cash flow, or redirecting additional profit into retirement accounts and investments. The objective is not simply to reduce this year's tax bill. It is to improve what you are able to keep and what you are able to build. I compare the plan choices in my Solo 401(k) versus SEP IRA guide.
5. Plan the timing of income and major purchases.
Once I understand the business and its cash flow, I can start making proactive decisions about timing. If equipment, vehicles, real estate, or other major purchases are coming, I determine whether completing those transactions this year or next year makes more sense.
I also look at the timing of income, expenses, retirement contributions, bonuses, capital expenditures, and other transactions before December 31 rather than discovering them after the year is already over. Tax planning becomes significantly more powerful when decisions are made before the transaction occurs. I cover one common purchase in my guide to the business vehicle tax deduction and the contractor side in my guide to bookkeeping and taxes for Florida contractors.
6. Layer strategies as the business grows.
Finally, I keep building on the foundation. As income grows, new opportunities may become available. Retirement plans can become more sophisticated. Real estate may enter the picture. New entities may be appropriate. Estate planning, succession planning, acquisitions, or advanced tax strategies may eventually make sense.
But those strategies should not be implemented simply because they sound impressive. They should solve a specific problem or move you toward a specific financial goal.
That is where tax advisory becomes different from tax preparation. Instead of looking backward once a year and reporting what already happened, I continually evaluate the business, make adjustments, and layer strategies together.
Over time, those decisions compound. Savings in one area can fund a retirement contribution. Better cash flow can fund an investment. Better structure can create additional planning opportunities. And each layer makes the next one more valuable.
The objective is not one big tax strategy. It is building a coordinated system where your business structure, taxes, cash flow, savings, and investments are all working together.
How the work runs
A licensed CPA on your numbers all year.
I am Timothy LeGendre, a CPA licensed in Florida, license #AC62625. The planning is mine, I sign the returns and estimates, and you have a direct line to me when something changes.
Most of the moves that lower a tax bill close on December 31, so the work is spread across the year rather than compressed into filing season. I watch the numbers as the year develops, adjust estimates as profit moves, and bring you decisions while there is still time to make them.
It works because I am not guessing at your numbers. My bookkeeping clients' books are current every month, which means every tax conversation starts from what the business is doing right now, not from a return that closed a year ago. Every strategy I recommend is documented against the statute, so it holds up if anyone asks, and the same numbers feed the return I prepare at year-end.
In their own words
What clients say about working with me.
Ready to see the bill coming for once?
Bring your last return to the call. I'll tell you honestly what I see, including if it is already being done right.
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