A roundtable with M&A, valuation, finance, operations, and marketing experts on why the coming ownership transfer will compress multiples for owners who wait, and how strategic positioning is quietly becoming the biggest lever on exit value. 

Most business owners still assume that if they build a healthy company, buyers will show up when it’s time to sell.  That assumption is getting expensive. 

By 2035, roughly six million small and mid-sized US businesses will face an ownership transition, representing about $5 trillion in enterprise value, according to a McKinsey Institute for Economic Mobility report. More than half of US small-business owners are already over age 55, and one in four are over 65. The Federal Reserve’s 2025 Small Business Credit Survey found that 62% of owners have seen their retirement timeline accelerate in the past five years. Peak transaction years are projected to land between 2027 and 2028. 

Translation: a wave of similar businesses is about to hit the market at the same time, chasing a limited pool of qualified buyers and capital. 

To unpack what this actually means for owners, we brought five perspectives to the table. Dave Blanchard, who advises  small business owners on growth and marketing strategy. Kristin Young, an M&A advisor with Trans World Business Advisors. Joe Orlando of Exit Strategies Group, who leads the business valuation practice inside an M&A advisory firm. Amanda Morrison, who prepares businesses financially and operationally for sale with NowCFO. And Ryan Olson, Consulting Partner at ERA Group, who leads cost optimization work for companies preparing to transition. 

What follows is the heart of that conversation, and what it means for owners planning an exit in the next three to five years. 

The market is shifting from scarcity to competition 

For decades, the assumption underneath most exit conversations has been that demand for good businesses would always exceed supply. That assumption is no longer safe. 

 Kristin named the shift in three words:  “We’re looking at what we lovingly call the silver tsunami. All these people are getting ready to exit.” 

Joe framed the buyer-side math bluntly: 

“The owners want to sell at the absolute high. And they want to buy at the absolute low. If you ever bought stock on the exchange, you know that’s virtually impossible unless you have some type of magic eight ball that tells you when to buy and sell.” 

 Kristin sees a wider set of doors than most owners consider when they think about “exit,” and it matters because each door has a different price: 

“A seller has to be ready to exit. It’s going to happen no matter what. You’re going to sell it. You’re going to give it to your kids. You might have to close your doors if your business is not ready to sell and you can’t find a buyer for it. Or you might die. One of those things is going to happen. Which one do you want to be in?” 

 Only 20% to 30% of businesses that go to market actually sell, according to Exit Planning Institute data. Roughly half of small business owners over 55 still have no formal succession plan, according to the Forbes report on the McKinsey findings. Those numbers were already sobering when supply was normal. In the coming oversupply, they will be worse. 

More supply changes how buyers evaluate risk. When a buyer has more comparable businesses to choose from, they get more selective. The question stops being “is this a good business?” and starts being “is this the best business among the ones on my shortlist?” 

Joe walked through the math on why that selectivity translates directly into a lower multiple: 

 “Those cash flows have to be discounted back to today. If there’s risk, like key person risk, customer concentration risk, supply chain risk, that’s just going to lower the value. Increase the risk, lower the value, all other things being considered when you’re looking at it from an income approach. A market approach when you’re applying a multiple, those multiples are going to be higher for higher margin businesses.” 

 Ryan added the operational lens. Buyers are actively looking for holes: 

 “Profit consists of two things. It’s the money you bring in and the money you hold on to, what you’re not spending. There’s a lot of businesses where money is leaking out through different areas they don’t even realize. That’s going to have a big impact on the EBITDA and then the valuation of the business.” 

 His favorite example is a client whose shipping costs had been quietly inflated for years:  “We got looking at it and found this vendor was overcharging our client by a million dollars a year on their shipping costs. Nobody was looking at it because the shipping team was happy. Everything was, you know, it was just business as normal. And they even bring us donuts every Friday.” 

In an oversupplied market, the buyer’s diligence team will find that million-dollar leak. And they will price it into the offer. 

Healthy performance alone may not protect your multiple 

The most expensive assumption an owner can make right now is that solid financials will carry them through the exit process. Joe told a case study that should be required reading for anyone within five years of selling: 

 “The situation I’m currently working on. The owner wanted to sell the business, but said two or three years ago that I want to wait two or three years. They didn’t do any preparation. Then his wife got diagnosed with Parkinson’s and he said, I need to take care of her. What ended up happening was we got initial indications of value at twenty five million. And because he took his eye off the ball, the purchase price now is twelve million dollars.” 

 The kicker was the owner’s response to the halving of his exit value: 

 “His point is, well, I’m losing all this money. And I’m saying, well, you took all that money out of the business. He took twenty million out of the business in distributions over the last five years. I said, your business would be worth forty million dollars if you’d reinvested it in systems and operations and a level of management that can take over the business when you leave.” 

Dave connected that back to a decision framework every owner should be honest with themselves about: 

 “If you’re withdrawing capital from the business, you’re essentially harvesting it yourself as opposed to wanting to get value out of selling it. That’s okay if that’s what you want to do. It’s a matter of being clear about what you want to do and how you want to extract the value out of your business.” 

That is the choice under the surface of most exit conversations. Harvest cash today or reinvest to build terminal value tomorrow. Both are valid strategies. But you cannot do the first and expect the second. 

Valuation is becoming a positioning problem, not just a finance problem 

Here is where the two forces in this conversation collide. As supply rises and buyer scrutiny rises with it, the businesses that hold their multiples are not just the ones with clean financials. They are the ones that also present clearly, differentiate credibly, and reduce the buyer’s perceived risk faster than the alternatives on the shortlist. 

Dave framed the marketing side of exit readiness around four pillars that materially influence buyer perception of risk: 

“From a marketing standpoint, there’s four different pillars that can support a higher valuation. Customer profitability. Customer diversity, because customers can go away, and that’s a big risk factor for a buyer. Putting a system in place that drives growth without the owner. And extracting the owner from the day-to-day involvement in marketing decisions. Every business needs a growth engine, and a lot of times if you take the owner out of the business, the growth engine goes with them. And therefore much of the value.” 

Notice that only two of those four levers are financial in nature. The other two, systematic growth and owner extraction, are strategic and operational. They determine whether the business you have built can be understood, transferred, and scaled by someone else. 

That is the positioning problem. And it is why marketing leaders, not just finance leaders, belong in exit planning conversations three to five years before due diligence starts. 

Dave shared a small illustration from a prior client engagement that shows how off-base most owners are about why their customers actually buy: “I was working for a luxury dog hotel franchise. The owners thought it was all about luxury and they had chandeliers and dog TV and leather couches. But we asked customers why they chose them. And they said, well, my dog comes home tired and happy, the staff loves my dog and my dog loves the staff, and the place is immaculate. So luxury was not even the top ten in terms of reasons to purchase. When we shifted the marketing and branding around those three things, the communication became much more effective.” 

If owners are wrong about why their own customers choose them, buyers will notice. And the story of “why this business is worth a premium” will collapse under the first serious diligence question. 

Buyers pay more for businesses they can understand and scale without you 

Amanda made the operational version of the same argument with a memorable test: 

“If you can’t step away from your business for two weeks a month and everything run like you were there, you’re not really selling a business. You’re selling a business that really relies on you. If you’re the key person holding all the plates up, you’re not really selling a business at some point, you’re selling a job. And that’s not necessarily what people are willing to pay high dollar for. Build those systems within your company three to five years before, so that you can go to Mexico for a week or for a month, and no one knows the difference.” 

Kristin took the psychological version:

“One of the biggest issues that we have is getting owners to get their claws out of the business. You better be able to walk away for sixty days and your business better not go. If you can do those three things, if your marketing is operating without you, your operations can operate without you, your financials can operate without you, then you have a sellable business.” 

 Both describe the same phenomenon from different angles. A business that only works because the owner is in it is not fully transferable. And what buyers pay for, at the multiple level, is transferability. 

Valuation improvement begins years before due diligence 

Amanda made the most practical case for early preparation: “Thinking about it three to five years before you actually want it to happen is the most important part, especially from the financial side. Making sure that you have stable revenue, stable EBITDA, that your chart of accounts makes sense to the buyer. But that takes time. You can’t do that overnight. The value isn’t there. You can’t go back and restate things.” 

Joe agreed, and named the trap that catches most owners: “It’s hard to sell a business when you restate or normalize the earnings. It’s hard to sell that to a buyer.” 

Kristin closed the loop with the simplest possible answer to the question owners ask her most: 

 “The number one problem that we run into is that person who comes up and says, I want to sell my business. What’s it worth? I want to sell it tomorrow. And we’re like, listen, you’ve got to prep. Doesn’t matter whether you are five years out or ten years out. The number one thing right now for owners to be thinking about is when should I start? And that’s now.” 

Better exits come from aligning finance, operations, and marketing 

The clearest theme across the entire conversation was that exit value is not built inside any single department. It is built by aligning finance, operations, and marketing to tell one consistent, evidence-backed story about a business that will keep working after the owner leaves. 

 Amanda made the case for bringing outside expertise in early: “Bring in your partners, bring in your people that you know you can depend on and make sure you’re getting good advice as far as that goes.” 

 Joe named the ROI most owners underestimate: 

“Business owners fail to understand that they will get a much higher ROI by spending money to bring someone like Amanda O’Reilly in as opposed to doing it themselves. They know the business and they probably could get to that point, but they don’t put any value on their time. They could be much more productive running the business than thinking about all this stuff.” 

 Ryan added the cost-side version of the same principle: “For all of these different cost categories, it’s ideal if you can bring someone in that has expertise in these different areas, that can help find those options.” 

 Dave summarized the marketing readiness framework: 

“Do you have a clear goal for marketing? Do you understand your buyer? Do you have a clear brand that’s different than your competitors, in a way that’s easy to communicate? Do you understand how sales and marketing work together? Do you have a cadence for planning? And are you investing where your marketing is paying off?” 

 Kristin was the one to name what actually happens when finance, operations, and marketing are not aligned before an exit: 

“Those people who wait till the last minute to ask, what’s my business worth, I want to sell it tomorrow, are the ones who never get the value they should have for their business. Because they didn’t bring the third parties along that they needed. They didn’t look at the valuation on a regular basis. They didn’t bring in the person who might want a job to buy their business. Think about it now. Doesn’t matter where you are. Think about it now.” 

The new buyer, and the new opportunity 

Toward the end of the conversation, Joe surfaced an idea that changes the landscape for owners without an obvious successor. The pool of buyers is not just private equity, family offices, and strategic acquirers. There is a rising generation of young operators who cannot afford homes but can, with the right structure, afford a business. 

“Someone at that age is looking to build equity. Equity in a house. They can’t afford to buy a house. I said, why not build equity in a business? As a young buyer, tell someone that’s three to five years away from selling their business, hey, I want to buy your business. I’ll pay you a salary and we can figure out a value. Building equity in a business is not only easier, it’s exponential. Or it can be. You can’t get that multiple of value from a house.” 

 Kristin agreed, and named where she has seen this work best: 

“The best buyers I’ve found are employees around there because they already know the business. They have ideas about how they can make it better. There’s trust. Trust does not exist when you go to sell a business. Transparency doesn’t exist. Everything changes when you get a young person with a ton of energy coming in who knows the business and is passionate about it, already knows the people.” 

 Amanda extended the point into a broader succession strategy: 

“It solves that job versus business conversation. If you really are the glue that holds your business together, hire someone that can come and stand next to you and teach them the ways and pass that business on to them. Just because you’re in that position doesn’t mean you need to close your doors. There’s so many tradesmen and those types of businesses that really are the bread and butter. There are a ton of young people in this next generation coming up that want to be taught those things.” 

For owners staring at the silver tsunami, this is one of the more useful reframes in the entire discussion. The buyer pool is bigger than it looks. It just requires investing in the transfer earlier, and being open to a wider definition of who your buyer might be. 

The takeaway for owners 

The market is shifting from scarcity to competition. A generation of owners is preparing to exit at roughly the same time, and buyers will have more options and more leverage than they’ve had in a generation. 

In that market, valuation stops being purely a finance exercise and becomes a marketability problem. Cash flow still matters. Multiples still get applied. But the multiples themselves will be shaped by how clearly your business differentiates, how credibly it can operate without you, and how confident a buyer feels that the value you built will still be there twelve months after the sale closes. 

That is a marketing and positioning problem as much as a finance one. And it starts long before due diligence. 

 For owners planning an exit in the next three to five years, the highest leverage moves are the ones that make your business easier for a buyer to understand, scale, and trust. Cleaner financials. Diversified customers. A repeatable growth engine that doesn’t require your presence. A story about the business that holds up when a buyer’s diligence team stress-tests it. 

 Or, as Kristin put it: think about it now. Doesn’t matter where you are. Think about it now. 

 Watch the full conversation below:

About the participants 

• Dave Blanchard advises, small business owners and founders on growth strategy, marketing readiness, and buyer perception.
• Kristin Young is an M&A Advisor with Trans World Business Advisors, focused on preparing and selling small and mid-sized businesses.
• Joe Orlando leads the business valuation practice at Exit Strategies Group, an M&A advisory firm. 
• Amanda O’Reilly helps owners prepare their financials, accounting, and operations for a sale, and sits alongside sellers during the transaction. 
• Ryan Olson specializes in cost intelligence and supply-chain optimization for companies preparing to transition, protecting EBITDA and reducing hidden risk. 

Sources 

• McKinsey Institute for Economic Mobility: Navigating the Great Small Business Ownership Transition 
• Forbes: Millions of Small Businesses Soon Changing Hands as Baby Boomers Retire 
• Fortune: The Great Small Business Wealth Transfer, McKinsey Sees $5 Trillion of Baby Boomer Companies Coming Up for Sale 
• Federal Reserve Small Business Credit Survey 2025 
• Exit Planning Institute: Small Business Exit Data and Owner Readiness Research