How to Plan Your Business Exit: What an M&A Advisor Learned Selling His Own Company

By Sam Taggart

CEO and Founder

Door to Door Sales•October 3, 2026

Most owners who learn how to plan a business exit learn it the hard way, in the middle of the deal. Carey Sobel had every advantage going into his own exit. He had spent the better part of 13 or 14 years as a business broker and M&A professional. He knew how deals work from the inside. And he still says he broke a lot of the rules he now teaches.

On the CEO Roundtable, Sam Taggart and JD Beck sat down with Carey, whom they met while he was brokering one of the M&A deals the team is doing at Forge. Carey is a partner at Boss Group International on the M&A side and the Chief Acquisition Officer at Coastal. What follows is his playbook for planning an exit, finding the real value of a business and preparing for the parts of a sale no spreadsheet covers.

The Exit That Taught an M&A Advisor the Hard Lessons

Carey's marketing and advertising agency grew to "12, 13 million in top line, about 3 million in EBITDA." He decided in 2019 that he wanted out. The transaction did not close until March of 2024.

COVID hit first. Then came the agency's two best years, 2021 and 2022. By 2023 the partnership was strained, and Carey said the writing was on the wall for marketing and advertising because of AI influence and the job market. So he went to his partner with a plan built to make the buyout easy.

"I went and secured a term sheet through SBA so he could buy me out with no cash out of pocket," Carey said. He set a value he thought the business was worth and took 80% of it for the term sheet. The two had a four-hour conversation and shook hands.

Two weeks later, his partner pushed back. "He goes, I'm going to re-trade on that deal. I don't like the price."

The next step was a third-party valuation. It "came in two and a half million dollars more than my valuation." After 60 to 90 days of back and forth, Carey settled on terms he "felt was selling myself a little short." He also took "damn near 40% on a seller's note to get out of that business," which is why he now tells his sellers to keep the seller's note or earn-out "as low as you possibly can."

The Three Legs of Exit Planning

It was only after his own deal closed that Carey earned the CEPA designation through the Exit Planning Institute. The framework he learned there now shapes how he advises his clients. He calls it "the three legs of the stool."

Leg 1: The Attractiveness and Readiness of the Business

"The first leg, which is the attractiveness and readiness of a business to sell. And that's what most M&A advisors work on, right? What's the business worth? Is there continuity?"

Leg 2: Your Personal Financial Picture

"What is your net worth? What do you need to retire? That's the wealth gap. And how much of your net worth is locked up in your business? Because most business owners have 80% of their net worth locked up in it."

Leg 3: The Emotional Side

"People truly don't know the emotional aspects that go into selling your business. And it's everything from your identity, what are you going to do afterwards?" Carey asked owners to think about whether they are "okay not being the man, having so many people rely on you and ask you questions and calling the shots."

He admits he ignored this leg completely. "I didn't really think about any of the emotional side. I just wanted to get the hell out of the damn business."

Focus Is What Makes a Business Sellable

Before Carey could build something worth selling, he had to stop doing everything at once. In his early to mid-20s he had "seven or eight different businesses running at once, but none of them were doing well." His conclusion was blunt: "I'm pretty damn good at starting the business. I am not a good operator."

So he consolidated. He sold his entertainment business, stopped practicing residential real estate, sold his bars and hospitality concepts, and focused on the agency and brokering on the side. When he was deciding whether to exit the agency, he hired an executive business coach in her mid to late 70s. Her advice: "Saying no is so powerful. Saying no shows that it's more, um, exclusive to get your time. Your time becomes more valuable."

The First Questions Carey Asks Every Seller

Sam asked what Carey looks at first when an owner says, help me sell my company. Before he ever opens the financials, he asks three things.

• Why are you selling? Divorce, death or a move all make sense. "It's very rare that somebody calls me up and goes, my business is crushing it, I want to sell right now. That's a smart businessman or businesswoman."
• Why now? "There's a lot of ways that you can structure a deal that don't include getting out completely." He pointed to options like an ESOP or "a recapitalization, minority or majority."
• How involved are you in the business? An absentee owner is more attractive "because I know that the business runs without that person, so it's probably a more valuable business." The owner who brags about working 60 hours a week and handling finance and sales? "That's not good."

Why the Emotional Side Can Kill a Deal

"We really are therapists," Carey said of M&A advisors. Every deal has curveballs, and the reactions to them are "always so emotionally driven by a seller and a buyer too." The only way to keep emotion from taking over is to "prep them from the beginning on what they're going to go through."

That prep means having the team in place: legal, an M&A-involved accountant, and every owner on board. "Make sure their spouses are on board," he said, and know exactly who else owns the business. "I had a $12 million transaction die because a 1% stakeholder wouldn't sign off on it."

He also described a recent listing, an aluminum business worth about 26 to 28 million dollars, owned by a husband and wife who are 43 and 44. They "played ping pong for three months," wanting to sell one day and keep it the next. The answer was a middle path: find a group they believe in that can get them "from working 70, 80 hours a week to 30 or 40."

Sell on the Upswing, Not the Peak

JD called this the point he has the strongest opinion on: "Consider selling when you're doing well and you're growing. Not when you're peaked and not when you're on the decline."

The risk shows up in diligence. "If they start declining in revenue and their EBITDA starts to drop, they are going to get crushed," JD said, and a decline invites "a massive retrade."

Carey's fix is to always know your number. "Getting a broker's opinion of value or a informal or formal valuation on your business, there's never a bad time to do that to understand what the benchmark is." He warned against the "one more year" trap: "What will happen if there's another COVID?"

Owner Value vs. Market Value: Let the Market Set the Price

Every owner has a number in mind. Carey's experience is that it is almost always off. "99 out of 100 times they're wrong, right? Because they're going to put more emotional value on the business."

He shared one owner's reaction to his opinion of value: "Well, I ran the business for 30 years. I can't only walk away for this, this amount." Carey's view is that no single opinion, including his own or a certified appraiser's, beats the open market. "There is no more validity to his number or my number than there is to putting it on the open market and seeing what people are willing to pay for it, because that is what a business is worth."

How a Structured Sale Process Finds the Real Price

For larger deals, Carey's team runs a structured sale process and brings the business to market without a price.

• Package and list. A listing agreement is signed with the lowest amount the seller will accept, but that number is not shown to buyers.
• Go wide. The package goes out to a "proprietary database of about 40,000 active buyers across the country," from private equity groups to family offices to individuals leaving corporate America.
• Let it work. For three or four weeks, NDAs get signed, buyers get qualified and information is released slowly.
• Collect IOIs. Buyers send an indication of interest with a price range or a multiple, such as "four to six X of the trailing 12 months of P&Ls."
• Narrow to LOIs. The strongest groups move to letters of intent, management meetings and a purchase contract.

His last deal brought in "350 NDAs. We got 43 IOIs, narrowed it down to 12 LOIs, six management meetings, one purchase contract." Once the IOIs arrive, he said, "you pull out the outliers, you've just determined the market value of the price."

It can also surprise sellers in a good way. One owner asked Carey if his business was worth anything. Carey thought he could get him close to 5 million. The deal was set to close "for 8 million with only $500,000 on a seller's note. Seven and a half cash up front."

Get a Quality of Earnings Before You Go to Market

One of the biggest changes in Carey's business is that, most of the time, he now requires sellers with a sizable enough business to get a quality of earnings (Q of E) before going to market. He described it as "essentially a, um, forensic analysis on, uh, a business's financials."

Owners often buy heavy on materials and expenses at year end to cut taxable income, hold checks or delay deposits, and then there is the move from cash to accrual accounting. A Q of E normalizes all of that. And since "in most cases that buyer is going to get a Q of E anyway," the seller should be armed with the answers first. In his words: "Let's get all the ... skeletons out of the closet at the beginning."

JD said it can cut two months out of diligence, and Carey added that a completed Q of E goes up front in the marketing package, telling private equity groups, "hold on a second, we got a sophisticated seller here." It is also a seriousness test. "If one of my sellers is going to spend 20, 30, 50 grand on a Q of E, they're pretty committed to selling their business as well."

If you want a head start on getting your financials buyer-ready, read Get Your Numbers Right Before You Sell Your Company.

Write the Manual for Your Business

JD asked for one piece of advice for any future seller. Carey's answer was documentation. "Too many hats are worn by the owner. And I would always encourage the owner of a business to do everything that they can to get completely out of the business."

That includes the relationships. If all of the owner's relationships run through them and they are doing the sales, those need to move to "somebody else so you have a really strong management team, which makes the business so much more transferable and sellable."

His brokerage just went through the exercise itself, writing an SOP for everything from sending an NDA to contracting a company for due diligence. "If I got hit by a bus tomorrow, somebody could come in and pick up that manual and if they were halfway intelligent, they could understand how to operate my business."

If you are still the person every decision runs through, start with Stop Being the Bottleneck: A 30-Day Plan for Home-Service Owners.

Start Planning Your Exit Now

For more on running your company in chapters with the end in mind, read Business Exit Planning: Every Owner Exits, So Plan for It Now, and see what the legal side looks like in The Attorney Can Kill Your Deal. If you own a roofing company and want to know what it could be worth, start with a Forge Strategic Equity valuation.