M&A
How to sell a business: the steps from your decision to closing day
You are ready to sell, or close to it, and the advice arrives in pieces. This is the whole path in order, what each step asks of you, and how long it takes.
A child asks whether to plan on running the company, or your best manager asks about buying in. Here is how to compare successors, the numbers each one needs, and how far ahead to start.
By Surfside Capital AdvisorsPublished 7 min read

Succession planning for business owners means deciding who will own and run the company after you, how they will pay you, and when control passes. The usual successors are a family member, a manager, a partner, your employees through an employee stock ownership plan (ESOP), or an outside buyer. Start years ahead, because a successor takes time to prepare.
A child asks whether they should plan on running the company, your best manager asks what it would take to buy in, or a health scare makes you wonder who would sign payroll next month. Each is the same question with two halves: who will own the business, and who will run it. They are often different people.
It covers four decisions: who owns the business next, who runs it, how and when you are paid, and what happens if you cannot work before the handover. A business succession plan is the written version, with dates, a price or a method for setting one, and the terms of payment.
Exit planning is the wider work of deciding when you leave, what you need from the business, and which exit you take. Succession is the part that names the person, and even an outside buyer will ask who runs the company after you.
Five kinds of successor cover most cases, and the biggest difference between them is how you get paid.
| Successor | How you are usually paid | What has to be true | What to watch |
|---|---|---|---|
| A family member | A gift, a sale, or a mix, often over years | They want the job and can do it, and the family agrees on what is fair to children outside the business | Gift and estate tax rules |
| A manager or management team | Their own cash, a bank or SBA-backed loan, and often a note you hold | The business can carry the debt after paying someone to do your job | Part of your price depends on results after you leave |
| A partner or co-owner | A buyout under your buy-sell agreement, often funded by life insurance | A price or formula in the agreement, and money to fund it | How the agreement is structured can change the tax result |
| Your employees, through an ESOP | A sale of your shares to the plan | Payroll and cash flow large enough to support the plan | Independent appraisals and years of plan administration |
| An outside buyer | Cash at closing, sometimes with part of the price paid later | Financials and a company a stranger can check and run | A process that takes months |
A management buyout is a sale of the company to the people who already run it. An ESOP is a qualified retirement plan that must be designed to invest primarily in the employer's own stock, according to the IRS, and federal tax law requires an independent appraiser to value the private-company shares it holds. If you own an advisory firm, when is the right time to sell your RIA covers the extra steps.
Start from what you need, then test each candidate against three questions.
Ownership and management can be split, with a family member owning the shares and a hired manager running the company. When no one in the family wants to own or run the business, a family plan does not fit, and the choice is among a manager, a partner, your employees, and a buyer.
You need four: a value range, the amount you need after tax, what the business earns once your job is paid at market rates, and what each successor can afford.
For a gift of shares, the IRS uses fair market value, the price at which property "would change hands between a willing buyer and a willing seller," both with reasonable knowledge of the relevant facts (Treasury Regulation 25.2512-1). A range built the same way shows what you give up when you set an insider's price below it, and how to increase business value before an exit covers what moves it.
Your own number is what you need after tax, and by when. Payments spread over ten years are worth less to you than the same total at closing, and they depend on how the business does without you.
Earnings without you are the ones a successor inherits, so replace your own pay with what it would cost to hire someone to do your job. The figures below are an illustration.
| Item | Today, with you in the job | With a manager paid at market rate |
|---|---|---|
| Earnings before pay for the top job | $900,000 | $900,000 |
| Pay for the person running the company | $150,000 | $240,000 |
| Earnings left for the owner | $750,000 | $660,000 |
In this example the successor inherits $90,000 a year less than you see. A buyer restates earnings this way, so do it first.
What a successor can afford usually comes from the business's future cash flow. SBA 7(a) loans of up to $5 million can fund complete or partial changes of ownership, according to the U.S. Small Business Administration, and how to finance a business acquisition covers what a lender will ask of your successor. If you are paid over time, the IRS's installment method generally lets you report the gain as the payments arrive, although gain from depreciation recapture is reported in the year of the sale and inventory does not qualify.
Your buy-sell agreement and a short contingency plan decide it. A buy-sell agreement is a contract among the owners, and sometimes the company, that says who may or must buy an owner's shares, and at what price or by what formula, when an owner dies, leaves, or wants out.
How the agreement is funded matters. In Connelly v. United States (June 6, 2024), two brothers' company held $3.5 million of life insurance on each of them to buy back a brother's shares at his death. The Supreme Court held that the company's obligation to redeem the shares did not offset the insurance proceeds in valuing the company for estate tax, which cost the estate $889,914 in additional tax. The Court noted that a cross-purchase agreement, in which the owners buy each other's shares, would have avoided the risk that the insurance proceeds raised the value of the shares, with drawbacks of its own.
Check your own agreement for the price or formula, how the buyout is funded, and when the price was last updated. Then write one page for the first 90 days without you: who can sign payroll and pay bills, who speaks to the bank and the largest customers, and where the agreements and insurance policies are kept.
Count back from the day you want to stop running the business, because the slow parts are preparing a successor and building a record of results without you. A sale takes months once it starts, as the risk of waiting one more year shows.
No number of years fits every company. If you want out in five years and have no successor in mind, start with the numbers now, because they show which paths are still open. Exit optionality covers the groundwork that helps every path.
We set out the valuation range, restate your earnings the way a buyer or a lender would, and model how each successor could pay you and over what period, so you can compare the paths with numbers. That is part of our succession planning and M&A advisory work.
Under tax code section 1042, a C corporation owner can defer the gain on shares sold to an ESOP by reinvesting in qualified replacement property between three months before and 12 months after the sale. Among other conditions, the plan must own at least 30% of the stock right after the sale, and the owner must have held the shares three years. S corporation shares sold after 2027 can use the election on up to 10% of the amount realized.
A year leaves time to get the numbers and start a sale, and little time to prepare a successor who has never run the business. Choose among the paths a year allows, such as a partner already in the business or an outside buyer, and keep handing work to your managers so the company depends on you less while it changes hands.
General information, not legal, tax, or investment advice.
Figures and rules as published by these sources on the dates shown.
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