Artificial intelligence is giving some baby boomer business owners one more reason to sell: They don’t want to deal with it.
But walking away is not so simple.
For owners heading to market, AI is becoming more than a tech headache. It is becoming a test of the company’s books—and potentially its price tag.
Buyers and private equity firms want to know whether privately held companies have invested in AI, automation and other tools that can boost profits. But they also want answers to tougher questions: How were those costs recorded? Do they support the company’s earnings story? And was management making a smart bet—or just throwing money at the hottest trend in business?
“There are many boomers who are kind of just throwing their hands up,” said Joshua Chananie, a partner, board member and consumer products leader at SAX Advisors, an independent accounting and advisory firm.
Many of those owners built their companies in a different era, when relationships mattered more than software. Now, they know AI is important—but “they don’t understand what’s going on,” Chananie told Thomson Reuters in a May 1, 2026, interview.
That confusion is helping push some owners toward the exits.
They “don’t want to take the time” or make “the effort to learn it,” he said.
AI Joins the Deal Checklist
AI has gone from back-office buzzword to deal-table issue.
Potential acquirers want to know whether a company is keeping up with competitors, where it is spending on technology and whether those tools are actually making the business better.
That can be a rude awakening for owners who have not cleaned up their books before a sale. Buyers are not just listening to management’s growth story. They are checking whether the accounting records back it up.
“Most people are not ready to sell and a deal falls out of the sky that becomes too good to turn down,” Chananie said. “It becomes a fire drill.”
That fire drill can mean cleaning up accounting records, preparing sale materials, going through a quality-of-earnings review and dealing with tax, trust and estate-planning issues before the deal closes.
Many owners do not have two or three years to get ready before testing the market, Chananie said.
For companies heading to market, AI is now part of the buyer checklist: what tools the company uses, what it is spending, how those costs are recorded and whether the technology helps management track performance, costs and profitability.
Owners who ignore AI because it seems too expensive or too complicated may pay for it later—in the sale price.
“In many cases, they wind up leaving a lot of money on the table because they did things the old way,” Chananie said.
The EBITDA Fight
The fight often starts with a basic question: How profitable is this company, really?
For owners who have spent money on AI or automation, some costs may be treated as regular expenses. Others, including certain software-development costs, may be capitalized on the balance sheet. Sellers may also try to add back AI spending to adjusted earnings if they argue it was one-time, unusual or tied to future growth.
That is where the stakes get real.
Many private-company deals are priced as a multiple of EBITDA—earnings before interest, taxes, depreciation and amortization. The higher the adjusted EBITDA, the higher the potential valuation. If buyers reject the seller’s adjustments, the price can fall.
In other words: the accounting can hit the deal.
Buyers, however, are getting tougher on technology-related add-backs.
Chananie said acquirers want to know whether a company made a serious, strategic investment in AI—or whether management was “just kind of throwing ideas at the wall and seeing what sticks.”
“The business has to evolve, but it has to evolve with a purpose,” he said.
Bob Michaels, head of the technical accounting practice at CrossCountry Consulting, said companies are wrestling with similar questions as they report results to investors.
“A key question is whether AI expenditures should be expensed as incurred or capitalized, and the answer is rarely straightforward,” Michaels said by email.
Some companies are also trying to keep AI costs out of adjusted earnings by calling them one-time or transformational investments, he said.
That pitch may be getting harder to sell.
“We are seeing companies try to characterize significant AI spend as a one-time or transformational investment to exclude it from adjusted earnings,” Michaels said. “That argument is becoming harder to sustain as AI costs shift from discrete projects to ongoing operating infrastructure.”
Have a Plan Before Buyers Ask
For owners who may sell in the next few years, advisers say the message is simple: get the AI story straight before buyers show up.
That means documenting what tools the company is testing, why the spending helps the business, how the costs are recorded and how the technology supports growth.
Buyers do not just want to see AI spending. They want to see a plan—and records to back it up.
The issue is also changing succession planning.
A few years ago, Chananie said, many owners were asking whether the next generation wanted to take over the family business. Now, some are asking whether they want to lead the company through another wave of technological change.
“I think AI is driving earlier exits than what most people expected,” Chananie said.
The fear is no longer just whether the kids want the company, he added. It is: “I’m afraid of the technology and what it means and what it costs because I don’t understand it and I don’t want to take the time to learn it.”
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