Owners preparing to sell a business naturally focus on the price. After years of building something valuable, they want an offer that recognizes the work, risk, and sacrifice behind it.

But the number in the offer is only the beginning. The more consequential number is what remains after taxes, transaction costs, and the obligations that follow the seller beyond closing.

On October 21, The Alternative Board Fort Worth & West hosted Gary Jackson, Tax Partner at the CJ Group, for the final luncheon in our 2026 four-part Optimizing Your Future Exit Series at Pappadeaux Seafood Kitchen in Fort Worth.

This article draws on Jackson’s presentation and accompanying handout. Credit goes to Gary also for uniquely organizing the content of his talk around a familiar football concept: offense, defense, and special teams. Each phase of Gary’s presentation addressed different ways owners can improve or protect the proceeds from selling their business from a tax perspective.

The starting point was clear: involve experienced transaction tax and legal advisors before negotiations narrow your choices. I will touch on a few points in this short article. To receive a copy of Gary’s detailed handout, you may reach him at gary.jackson@thecjgroup.com and reference his talk at Pappadeaux Seafood Kitchen in Fort Worth.

Offense Starts Before the Offer

An owner may assume tax planning begins once a buyer makes a serious offer. By then, some of the most useful decisions may already be harder to make.

The first question is what the owner actually owns and what the buyer proposes to purchase. A sale of the company’s assets and a sale of its ownership interests can produce different tax outcomes, even when the stated price is identical.

A buyer’s preferred structure may provide benefits to the buyer while increasing the seller’s tax burden. Understanding that difference gives the owner something concrete to negotiate.

The practical assignment is to have advisors compare the alternatives in writing. What would you receive at closing? What taxes would be due? What would remain available for retirement, family needs, or your next venture?

The handout also identified opportunities involving certain qualifying business stock, family gifts, trusts, and charitable planning. These are subjects for careful evaluation with qualified advisors; their usefulness depends on eligibility, timing, and the owner’s broader goals.

An intention to help family or charity deserves attention while there is still time to structure it appropriately.

Defense Means Finding Problems First

Tax preparation and readiness for a buyer’s investigation are different assignments. Filing annual returns does not necessarily mean the company’s tax history will withstand transaction scrutiny without questions.

Buyers examine sales taxes, payroll obligations, worker classification, accounting methods, and where the company may have filing responsibilities. Operations across state lines can add complexity that an owner has not fully considered.

Unresolved issues can become bargaining points. A buyer may seek a lower price, require money to remain in escrow, demand protection against future liabilities, or delay the closing.

That makes early preparation valuable even when there is no immediate sale planned. Assemble the records, identify potential exposures, and determine what should be corrected or disclosed before a buyer raises it.

Owners should ask their advisors a direct question: if someone investigated our tax position tomorrow, what would concern them most?

Finding the answer early gives the seller time to respond thoughtfully, with fewer surprises competing for attention during negotiations.

Special Teams Can Change the Outcome

The handout’s third phase of Jackson’s talk focused on the details that turn an attractive offer into the amount an owner ultimately receives.

A letter of intent can establish expectations about structure, payment terms, and other issues before the final purchase agreement is written. Owners need to understand those expectations before signing, particularly when they agree to negotiate exclusively with one buyer.

How the purchase price is divided among assets and other arrangements also matters. Money assigned to equipment, goodwill, consulting services, or a noncompete agreement may receive different tax treatment. The labels must reflect the transaction’s actual facts.

Payment timing raises another set of questions. A seller note or an earnout means some proceeds arrive later, perhaps only if specified conditions are met. The seller must consider collection risk alongside the tax consequences.

The agreement should also establish who handles tax returns, who receives refunds, and who bears responsibility if an earlier tax issue surfaces after closing.

These provisions deserve attention alongside the headline price. They help determine how much remains accessible and how much uncertainty the seller carries into the next chapter.

Start With What You Want to Keep

For an owner considering an exit, a useful first step is a coordinated conversation with transaction counsel, a tax advisor, and the advisors helping plan life after the business.

Ask them to connect the proposed transaction to your personal financial goals and show the likely proceeds under different structures.

That conversation should happen before an offer creates urgency, when the owner can still weigh alternatives and decide which tradeoffs are financially acceptable.

The lesson from this final session reaches beyond taxes. A successful exit requires preparation while choices remain open. Knowing what you hope to keep helps you judge the offer you eventually receive.

About the Author

Ed Riefenstahl is the co-owner of The Alternative Board (TAB) Fort Worth and West, where for over 20 years he has facilitated peer advisory boards and has worked with over 100  business owners to improve performance and prepare for successful exits. He previously served as Director of the MBA Consulting Program at Texas Christian University’s Neeley School of Business, where he founded and led Neeley & Associates Consulting.

About The Alternative Board (TAB) Fort Worth & WEST

The Alternative Board (TAB) Fort Worth & West provides peer advisory boards, executive coaching, and proprietary systems and tools for owner-led businesses and leaders of nonprofit organizations. Each board brings together a small group of non-competing business owners who meet monthly in a confidential setting to share real-world experiences, challenge assumptions, and improve decision-making. TAB members also utilize strategic tools and frameworks enabled by AI that are designed to help align leadership teams, execute priorities, and build more transferable, valuable businesses over time.