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Jackim Woods & Co. · Owner briefing

The Owner's Side of the Ledger: A Personal Checklist Before You Sell

Jim Bates
Jim Bates
October 5, 2026 · 4 min read

Before you sell your business, get your own house in order: know the after-tax number you need, hire a transaction-experienced CPA and attorney, align every owner on price and terms, separate personal items from the company, and decide what role you want after closing. Owners who skip this negotiate without a clear position.

Most pre-sale checklists are about the business: the financials, the contracts, the management team. Those matter, and buyers will test every one of them. But a sale also has a second set of preparations that no buyer will ever ask about, and owners who skip them tend to discover the gaps at the worst possible moment, usually with a letter of intent on the table and a deadline attached. This is the owner's side of the ledger.

1. Know the number you need, not just the number you hope for

Every owner has a figure in mind for what the business is worth. Far fewer have worked out what they actually need from the sale. The two are different numbers. The useful one starts with the purchase price and subtracts debt to be repaid, transaction fees, and taxes, then compares what is left against what you need to fund the next stage of your life. Owners who do this math before going to market negotiate with a clear floor. Owners who do it after signing an LOI sometimes find that a headline price they were thrilled with does not get them where they need to be.

2. Put your own advisors in place early

The buyer will arrive with a team that does this for a living: transaction attorneys, accountants running a quality of earnings review, and often a lender with its own requirements. You need a team that matches it. That usually means a CPA who has worked on business sales rather than only annual returns, a transaction attorney rather than a general counsel, and a wealth or estate planner. Much of the tax planning that can meaningfully change your net proceeds, from entity structure to estate and gifting strategies, has to be in place before a deal is signed. Bring these people in a year or more ahead, not the week the LOI arrives.

3. Get every owner on the same page

If you have partners, family shareholders, or a spouse with a stake in the outcome, the most important alignment conversation happens before any buyer is involved. Do all the owners agree on whether to sell, the minimum acceptable price, how much of it must be paid at closing, and who will stay on afterward and for how long? Disagreements that surface in the middle of a process are visible to buyers, and buyers read them as risk. A shareholder agreement that addresses how a sale decision gets made is worth reviewing now, while everyone is still on good terms.

4. Untangle what is personal from what is the company's

Over the years most owner-run companies collect a few personal threads. A vehicle or two, family members on the payroll, a personal guarantee on the line of credit, a building you own personally and lease back to the company. None of these are problems in themselves, but each needs a decision before a sale. Will the real estate be sold with the business or leased to the buyer? Which personal expenses come out of the financials, and are they documented well enough for a buyer to accept them as add-backs? Which guarantees need to be released at closing? Sorting this out early gives you cleaner financials and fewer surprises in the purchase agreement.

5. Decide what you want after closing

Buyers will ask how long you are willing to stay, in what role, and under what restrictions. Your answers affect the structure of the deal as much as the price. An owner who wants out at closing may accept less cash up front or a larger earnout. An owner willing to stay on through a transition can often negotiate better terms. Think about the non-compete you are prepared to sign, the role you want during a transition, and what you will actually do with your time. Owners who have not thought about life after the sale sometimes hesitate at the closing table, and buyers notice.

The takeaway

Getting the business ready to sell is half the job. The other half is getting yourself ready: a clear number, a capable team, aligned owners, a clean separation between personal and company, and a plan for what comes next. The business sets the price. Your preparation decides how much of it you keep, and how confidently you can negotiate for it.

FAQ

Questions practitioners actually ask

How much will I actually keep from the sale of my business?
It depends on the price, the structure, any debt that must be repaid at closing, transaction fees, and taxes. The structure of the deal and the tax planning done beforehand can shift the after-tax figure meaningfully, which is why it helps to model it with a transaction-experienced CPA before going to market.
When should I hire a CPA and an attorney for a business sale?
Ideally a year or more before you plan to sell. Some of the most valuable tax and estate planning must be in place before a deal is signed, and an attorney who has handled business sales can help you resolve contract and ownership issues before buyers find them.
What happens to real estate I own personally when I sell my business?
You usually have a choice: sell the property with the business, sell it separately, or keep it and lease it to the buyer. Each option has different tax and income implications, so it is worth deciding before you go to market rather than in the middle of negotiations.

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