The most expensive tax mistakes are made in deals, not in returns.

How you buy a business, structure a sale, admit a partner, or pay yourself carries tax consequences that last for years. These decisions are usually made without a tax strategist in the room. Advisory engagements put one there.

Schedule K&A — The Deal Before signing

Asset vs. stock salemodeled

Purchase price allocationoptimized

Earn-out treatmentstructured

Entity structurereviewed

Attorney coordinationin sync

Surprise after closing$0.00

A PARTNER IN THE ROOM — BEFORE THE INK IS DRY

Deals get structured by the people at the table. Make sure one of them is thinking about tax.

An asset sale versus a stock sale can change a seller’s after-tax proceeds by a large margin. A purchase price allocation signed without thought can cost a buyer years of deductions. A partnership agreement drafted without tax review can create phantom income. An S corporation owner paying themselves the wrong way can trigger an IRS examination or forfeit a deduction. None of this shows up on a return until it’s too late to fix.

Advisory work exists to move the tax conversation earlier: to the letter of intent, the term sheet, the operating agreement, the offer letter. That’s where value is created or lost.

When the decision outlasts the year.

Business owners

Owners buying, selling, merging, or bringing in partners, and owners who want an ongoing strategic sounding board, not just a preparer.

Real estate investors

Investors structuring acquisitions, syndications, joint ventures, and dispositions.

High-net-worth families

Families with closely held businesses, family entities, and generational transitions to plan.

Taxpayers under examination

Anyone facing an IRS or state examination who wants a credentialed advocate rather than a stranger.

A strategist across every decision that carries tax.

Transaction structuring. Asset versus stock sale analysis, purchase price allocation, installment treatment, earn-outs, and rollover equity.

Deal support. Tax due diligence for acquisitions and real estate purchases: what you’re really buying, and what it will cost after tax.

Entity strategy. Formation, conversion, and reorganization: S corporation, partnership, holding company, and multi-entity structures matched to how you actually operate.

Owner compensation. Reasonable compensation analysis, distribution planning, and retirement plan design for owners.

Exit and succession planning. Years before the sale, when it can still shape the after-tax number: structure, timing, and buyer readiness.

IRS and state representation. Notices, audits, appeals, and collections handled by an Enrolled Agent with unlimited representation rights.

An ongoing partner. When a decision has a tax dimension, you call before you sign. That’s the whole relationship.

Two ways to work together.

Project engagements

For a specific deal, restructuring, or examination, we scope the work, quote a fixed fee, and deliver: analysis, modeling, recommendations in plain English, and coordination with your attorney and the other side’s advisors.

Ongoing advisory

For clients who want a partner on call, our Strategy and Family Office plans include advisory access: the quick question, the sanity check before a signature, the modeling session before a big move. See Pricing & Service Plans.

The advisor is the one who answers for the advice.

Partner-level judgment. You work with a partner who has seen the structures, the deals, and the mistakes, and who stays in the room for the decisions that matter.

Clarity, not jargon. Recommendations come as clear options with the trade-offs spelled out the way you’d want them in a boardroom. Complex decisions become moves you can actually make.

Advice built to be defended. Jesse holds the Enrolled Agent credential alongside his CPA. Advice is given with the endgame in mind, and if the IRS ever asks, the person who advised you is the person who represents you.

Current on the new law. Author of The One Big Beautiful Bill, the Amazon #1 best seller on the 2025 tax law. The permanent provisions of that law reshape deal and entity planning; we plan with them every day.

Questions we’re asked before the first call.

When should I bring in a tax advisor on a business sale?

Before the letter of intent, if at all possible. The structure of the deal, asset sale versus stock sale, the allocation of price, and the treatment of earn-outs are negotiated early, and each one has a tax consequence. Advisors brought in at closing can only report what was agreed.

Should my business be an S corporation, a partnership, or an LLC?

It depends on your income, your owners, your growth plans, your state footprint, and how you take money out. There’s no universal answer, and the right answer can change as the business grows. We model the options against your real numbers and revisit as circumstances change.

Can you represent me in an IRS audit?

Yes. As an Enrolled Agent, Jesse holds unlimited rights to represent taxpayers before the IRS in examinations, appeals, and collections. See our IRS Representation page for details.

Do you work alongside my attorney and financial advisor?

Yes, and it’s how the best outcomes happen. Deals and structures involve legal, financial, and tax dimensions. We coordinate directly with your other advisors so the pieces fit.

How is advisory work priced?

Project work is quoted as a fixed fee after we understand the scope. Ongoing advisory access is included in our Strategy and Family Office plans. Either way, you’ll know the cost before we start.

Have a decision on the table with a tax dimension?

Call before you sign. A 30-minute conversation now can be
worth more than any deduction we’ll ever find on a return.