Service
Business Advisory
Entity choice, election timing, partner buy-ins, and financing decide most of your tax bill before there is a return to prepare.
Most of what determines your tax bill was settled before the tax year started. Which entity you formed. Whether you filed Form 2553, and with what effective date. How the operating agreement splits profit from capital. Whether the money you took out last year was payroll, a distribution, or a loan nobody documented. By the time the return is in front of me in March, those facts are history and my job is arithmetic.
Business advisory is the work on the other side of that line: entity selection and election timing, ownership and partnership structure, bringing on a partner or an investor, how financing gets treated, and unwinding a structure the business has outgrown. Sometimes it is one conversation and a written recommendation. Sometimes it runs across a year of decisions. It sits much closer to tax planning than to preparing a return.
Why the law degree matters here
I hold a JD from Florida State and a CPA license built on a bachelor's and master's in accounting from the University of Florida. That combination matters more on this page than anywhere else in the practice, because these are legal questions and tax questions at the same moment, and the two professions tend to see different halves of them.
Ask a business attorney whether to form an LLC or a corporation and you get a sound answer about liability, governance, and transfer restrictions. Ask a CPA and you get a sound answer about self-employment tax, basis, and section 199A. Neither is wrong. But it is one decision made twice, once in the formation documents and once on a federal election form, and the two halves have to agree with each other. When they do not, you are the one holding both pieces, usually a year later and usually in April.
So I read the operating agreement and I price what it says. A special allocation drafted to be fair between partners can produce a K-1 reporting income the partner never received in cash. A buy-sell funded the wrong way can trigger a taxable event at the worst possible moment. Catching that takes reading the document and knowing the code section. The drafting still goes back to a lawyer.
What people actually bring me
Not a menu of abstractions. These are the decisions that show up.
- Whether to elect S-corp treatment, and whether this is the year to do it
- Form 2553 timing, missed effective dates, and whether late-election relief is available
- Reasonable compensation for an owner-employee, documented against what the work is worth in the market rather than picked to hit a number
- Partnership allocations: what the operating agreement promises versus what the K-1 will report
- Bringing in a partner, including buy-in structure, capital accounts, and whether the first-year K-1 outruns the cash
- Asset sale versus stock sale when a practice or a book of business changes hands
- Debt versus equity in a financing round, and what an undocumented shareholder loan does to basis
- Whether a second entity earns the separate return, separate payroll, and separate bookkeeping it will require
The question is almost always framed wrong
The most common version I hear is whether to be an LLC or an S-corp. Those are not competing options. An LLC is a state-law entity. An S-corp is a federal tax election that an LLC or a corporation can make. Most of my small business clients are both, and the fact that the question keeps getting asked this way means somebody explained it badly.
The real question is narrower. At your profit level, does the self-employment tax you stop paying on the distribution portion exceed what the structure costs to run: payroll processing, a separate Form 1120-S, a higher preparation fee, and whatever filings a corporation picks up in your state? When profit is low, there is not enough distribution left after a defensible salary to cover those costs. When it is high, there usually is. The middle is decided by your facts, not by a rule of thumb.
Two things the S-corp savings tables online leave out. The Social Security portion of self-employment tax stops at the annual wage base, so once your salary clears it, splitting salary from distributions only saves the Medicare portion and the arithmetic gets much less exciting. And the 1120-S has its own failure mode: it is due March 15, 2027 for calendar-year 2026, and the late-filing penalty accrues per shareholder per month. On a multi-owner S-corp, a return that slips a few months can cost more than the first year of savings.
Form 7004 buys six more months to file a business return. Nothing buys back a missed election deadline. The expensive version of this conversation is the one that happens in April about a decision that was due the previous March.
How an advisory engagement runs
The first conversation
You describe the decision and the numbers behind it. No charge, no obligation. A fair number of these end with me saying the structure you have is fine and you should not spend money changing it.
Complexity assessment and a written estimate
Advisory work is scored against the same objective complexity model as every other service here. Entities involved, states filed in, and whether prior-year cleanup is in scope all move the number. You see the estimate in writing before I start.
The analysis
Projected tax under each option, the cash timing, the filing obligations each one creates, and what the structure costs to operate every year after that. Your numbers, not a general comparison.
A recommendation with a date on it
Not a list of considerations for you to weigh alone. A recommendation, the reasoning behind it, the deadline it has to clear, and a plain statement of what your attorney needs to draft.
Filing and follow-through
Elections filed with the right effective date, payroll set up if the structure requires it, and the first return prepared consistent with what we decided.
Where I stop and your attorney starts
I advise on tax and structure. I do not draft operating agreements, buy-sell agreements, or purchase agreements, and I do not form entities. Those are legal documents and they belong to a lawyer licensed in your state who represents you.
What I do is tell that lawyer what the documents have to accomplish for tax purposes, read what comes back, and say whether it does. The law degree makes me a faster reader of a draft and a better translator in that conversation. It does not make me your lawyer, and I will not blur that line to keep an engagement in-house. The same limit applies to money: I can tell you how a financing structure lands on your return and on your basis, but I do not source capital or broker a sale.
When you should not pay me for this
If you are a sole proprietor with one revenue stream and no employees, and a defensible salary would absorb most of what the business earns, there is no S-corp saving to chase yet. Stay on Schedule C, pay your estimated taxes on the quarterly dates, and come back when profit or headcount changes. An entity analysis at that level costs more than it can save you.
If the real problem is that the books are a mess and you cannot say what the business earned last year, an entity conversation is premature. That is small business accounting, and it comes first, because every structural recommendation depends on numbers you can trust.
And if you already have a CPA and an attorney who talk to each other, and you are satisfied with what they tell you, you do not need a third opinion. You need those two in the same meeting. Ask for it.
I came over to Nottingham after being with another CPA for many years. The transition was very smooth, and I love the personal attention I get from Hunter.
Start with the conversation
Tell me the decision in front of you and the numbers behind it. The first conversation costs nothing and carries no obligation, and you will leave it knowing what the options are, what the analysis would cost, and the date it has to happen by. Advisory work is priced the way everything else here is: a flat fee set by an objective complexity score, quoted in writing before any work begins.
Everything starts through the contact form. No documents travel as email attachments.
Other services
Further reading
Questions, answered plainly.
Is this a one-time engagement or an ongoing relationship?
Either one. A single decision, like an S-corp election or a partner buy-in, is a standalone engagement with a defined scope and a fixed fee. Other clients keep it open so a lease, a hire, or an equipment purchase gets run past me before it is signed rather than after. The ongoing version costs less over time, but only if you actually use it.
We have not formed the entity yet. Is it too early to talk?
That is the best time. Entity type, ownership percentages, and how capital accounts are set up are straightforward to get right at formation and expensive to unwind later. A conversation before you file the articles costs a fraction of the restructuring it prevents.
Can you fix a structure that is already set up wrong?
Often, yes. A missed S election can sometimes be cured under Rev. Proc. 2013-30, which allows relief within three years and 75 days of the intended effective date if the only failure was the late filing and the entity and every shareholder reported consistently with S status. Other problems, like a badly drafted allocation or a shareholder loan that was never documented, get fixed going forward rather than retroactively. I will tell you which category you are in before you pay me to work on it.
How is advisory work priced?
A flat fee, quoted in writing before I begin, set by the same objective complexity model used for every service here. The factors are countable: number of entities, states involved, whether there are existing K-1s or prior-year cleanup, and how many options need to be modeled. It is not hourly, so asking a follow-up question does not cost you anything.
The first conversation is free.
Tell me what's going on and I'll tell you plainly whether you need me.
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