On this episode of In Good Company, we explore what it really means to exit a business—and why the best outcomes are almost never just about valuation. Denis Horrigan and Kevin Leahy sit down with Ramsey Goodrich of Carter Morse & Goodrich to unpack the full arc of a business transition, from unsolicited offers and early curiosity to disciplined preparation, readiness, and finding the right long-term partner.
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Ramsey shares why thoughtful owners start with one question—why—and shift their focus from “selling a business” to designing a transition that aligns with their goals, legacy, employees, and future involvement. The conversation highlights a consistent theme: successful outcomes are built long before a transaction begins, through clarity of purpose, intentional planning, and the right advisory team working in sync. For business owners thinking about what comes next, this episode reframes exit planning as less of a moment in time, and more of a process of preparing for the life you actually want on the other side.
This podcast is produced by Connecticut Wealth Management, LLC, a registered investment adviser. This content is for educational purposes only and is not intended as personalized investment advice. Some guests on this podcast may be clients of the firm. Their participation does not constitute an endorsement of our services, and all discussions are focused on business insights rather than personal financial matters. Investing involves risk and past performance is not indicative of future results. Please consult with your financial professional before making any financial decisions.
Episode 3 Transcript:
Denis Horrigan: All right. Hello, and welcome to In Good Company. This is our podcast here at Connecticut Wealth Management, where we’re trying to create a community of business owners and the professionals who serve them. The goal is to help each other navigate challenges, address opportunities, and work through the issues that come with running a business.
We’re really trying to create a club-like environment where business owners can collaborate and learn from one another so we can all find success.
Today, we’re going to talk about something we discuss quite a bit with our clients: exit planning. One of the phrases we use around here is that exit is inevitable. You will exit your business. Everyone will exit their business. The question is whether you’ll do so with a plan.
Unfortunately, many people leave their businesses without a plan. Sometimes it’s unexpected—a death, a divorce, a disability, or any number of unforeseen circumstances. But we also spend a lot of time talking about how to intentionally plan for an exit, whether that’s internally to family members, a management team, or others, or externally through a sale.
Today, we’re going to focus on that external exit and what it looks like to sell a business. We have an outstanding guest with us, Ramsey Goodrich from Carter Morse & Goodrich, who is here to talk about what that process looks like, how it feels, and the key things business owners should consider.
So, Ramsey, welcome. Thanks for being here.
Ramsey Goodrich: Absolutely. Thank you for having me.
Denis Horrigan: Ramsey, why don’t you start with the Ramsey Goodrich story? Tell us about Carter Morse & Goodrich, what the firm does, your background, and how you got into this role.
Ramsey Goodrich: Excellent. Well, thank you. I’m thrilled to be here.
We love talking with business owners about what is often one of the most important decisions they’ll ever make. We actually try not to use the word exit. Instead, we prefer the word transition—whether that’s succession planning, partnering with private equity, selling to a third party, or pursuing another path.
That transition is critically important.
Carter Morse & Goodrich is a boutique investment bank headquartered in Southport, Connecticut, with offices in Providence, Rhode Island, and, as of June 1, Garden City, Long Island. We’re continuing to expand throughout New England.
What makes us unique is that we specialize in representing families and founders through what is often a once-in-a-lifetime transaction.
My own background is more traditional Wall Street. I started at JPMorgan Chase, working on large cross-border transactions. From there, I went to Banque Paribas. I left a big bureaucratic bank for an even bigger bureaucratic French bank.
Later, I joined Ernst & Young just before the technology bubble of 2000 and 2001. For the next generation that may not remember it, it was a fascinating period—great M&A activity on the way up, significant restructuring on the way down, and really the birth of private equity as we know it today.
I was fortunate enough to lead the Financial Sponsors Group there for a number of years, working with an outstanding team across the country. We did some really interesting work, but I eventually realized that my passion was still with families and founders.
Selling a private equity portfolio company to another private equity fund isn’t nearly as exciting as helping an entrepreneur navigate one of the most significant moments of their life. When you’re working on something so personal, unique, and important, it’s easier to bring real passion to the process.
Today, we focus exclusively on five old-economy industries. Manufacturing is our core area of expertise, but we also work extensively in business services, food and beverage, consumer products, and HVAC.
HVAC happens to be a particularly active industry right now. Whether it’s a hot industry or a cool industry, I’ll let you decide.
We operate primarily in the middle market. While our marketing materials say we work on transactions ranging from $25 million to $250 million in enterprise value, our true sweet spot is in the $50 million to $150 million range. That’s often a key transition point where businesses move from being owner-led organizations to truly professionalized enterprises.
Defining Success Beyond the Sale
Denis Horrigan: Awesome. So when a business owner comes to you—and we’ll talk about when they should come to you—but when they’re thinking about selling their business, aside from sale price and valuation, what do you think is the most important thing they’re actually trying to accomplish?
What are they really trying to achieve?
Ramsey Goodrich: You said it perfectly. Everyone is concerned about maximizing value. “Get me more.” That’s how we’re incentivized, and at the end of the day, the only measurable definition of success is purchase price. How much did you get?
The problem is that’s usually the wrong metric to focus on.
When we sit down with business owners, we spend time understanding the business and determining what we think it’s worth. We develop a solid estimate of what we believe we can achieve, but that’s only the beginning of the story.
The most important question is: What does the owner really want?
What’s their definition of success?
We use the word transition rather than transaction because most owners think about this process as very binary. They believe they either own 100% of the business, make 100% of the decisions, spend 100% of their time there—or they’re completely out.
The reality is that neither of those extremes is necessarily true.
The conversation is really about defining success and understanding what the owner wants to do after the transaction. We use a simple analogy: If you sell your business on Friday, you’re going to celebrate all weekend. That’s great.
But what do you want to do on Monday? And the Monday after that? And the Monday after that?
That question often changes people’s perspective.
Valuation is important. It’s the clearest and most tangible measure of success. But there’s much more to it. Ultimately, it’s about understanding what the transition leads to.
Denis Horrigan: When you talk to business owners about what they want to do on Monday, my guess is you’re often working with them for years.
Ramsey Goodrich: Ideally.
Denis Horrigan: Ideally, yes.
If you’re talking to them today about what they think they want to do on Monday, and then three or four years later they’re actually going to market, does that vision change? And how do you figure out what they really want to do? What’s that process like?
Ramsey Goodrich: That’s the hard part. That’s the art of the deal, not the science.
When these conversations begin, owners usually describe a broad goal. They want to retire, spend more time with their grandchildren, step away from the day-to-day, or they’re simply burned out. Sometimes, as I like to joke, their spouse finally won the argument.
Whatever sparks the conversation, it’s often difficult to fully understand the desired outcome until you’re evaluating the final group of potential partners.
And that’s an important distinction. Most people talk about finding a buyer. We prefer to talk about finding a partner.
A buyer implies the end of something. An investor implies a financial transaction. A partner implies helping the company move successfully into its next chapter.
What we often find is that many owners become excited about staying involved with the business after the transaction because they’ve found the right partner.
Once you get beyond the financial considerations and clarify your personal goals, legacy becomes incredibly important.
Owners often tell us, “I’ve spent decades building this company.” In some cases, it’s been in the family for generations. We recently worked with a sixth-generation company celebrating its 150th anniversary.
For owners like that, concerns about legacy, reputation, family identity, employees, customers, and community often become just as important as the purchase price.
That’s why the answer to the Monday question depends so much on the partner.
Once we understand the owner’s definition of success, we can help shape the right outcome. Many owners ultimately want to stay involved, just in a different capacity.
Instead of making every decision every day, maybe they move into a board role. Maybe they become a consultant. Maybe they focus on product development, which is what they loved when they first started the company. Maybe they concentrate on acquisitions or sales and leave HR, administration, and other operational responsibilities to someone else.
There’s no simple answer because every owner’s vision is different.
Denis Horrigan: You talk about this being a long process and about owners developing a definition of success. Does that definition change as they work through the process? As they have conversations with family members, co-owners, management teams, and other advisors, does their thinking evolve?
Kevin Leahy: Are they usually clear at the beginning? If you look back six months or a few years later, does what they originally described as success still hold true?
Ramsey Goodrich: Usually, it’s pretty close.
It’s never 100% accurate at the beginning, but it’s a valuable starting point for the conversation and for evaluating options.
We’ll often meet business owners who say, “I got a knock on the door. Someone offered me a huge number. I’m ready to sell.”
Our response is usually, “You haven’t really thought this through yet.”
What does selling actually mean to you? What do you want out of this process?
The money may be attractive, but you can’t make a life-changing decision based solely on the first offer.
Many times, when we’re talking with owners and management teams, they’ll say, “I’ll do whatever the buyer wants me to do after closing.”
That’s the wrong answer.
Tell us what you want first, and then we’ll find the right partner to support that outcome.
When someone says, “If they want to fire me, that’s fine,” they usually don’t mean it. So we spend a lot of time challenging those assumptions upfront and defining success before we ever make a phone call or build a transaction plan.
There’s almost always something deeper driving the decision. It may be age, health, family circumstances, or simple exhaustion.
One of the biggest themes we’re seeing right now is generational.
The children don’t want the business.
Many owners built their companies with the expectation that they would pass them down to the next generation. But increasingly, the next generation doesn’t want to run the factory, manage operations, or continue in the business.
It may be a highly successful company that generates significant wealth, but it isn’t the path their children want to pursue.
As a result, many owners find themselves saying, “I’m at a point where I want to spend quality time with my family while I’m healthy enough to enjoy it. My children don’t want the business. My management team may not be ready or may not have the financial resources to buy it. I need to figure out another solution.”
That’s where planning becomes essential.
And that’s why planning should begin years in advance.
The reasons owners start the conversation are often similar, Kevin. The outcomes, however, are almost always different.
Why Fewer Businesses Stay in the Family
Denis Horrigan: Are you seeing more family-owned businesses not being passed down to family members? Is that percentage of intergenerational transitions shrinking?
Ramsey Goodrich: Absolutely.
Statistically speaking, passing a business from one generation to the next becomes more difficult with each generation.
You often see a successful transition from the founder to the second generation. By the third generation, the percentage drops dramatically. By the fourth generation, it’s extremely rare.
If you look at the broader historical picture, many members of the Greatest Generation came back from World War II and built businesses. The Baby Boom generation often stepped into leadership roles and continued those businesses. Now we’re reaching the point where the third generation is facing a very different set of choices.
Many younger family members are pursuing professional, white-collar careers and have different interests and aspirations than previous generations. As a result, fewer of them want to take over the family business.
At the same time, we’re experiencing what I call the silver tsunami.
We believe there’s a tremendous wave of business transitions coming. In fact, it’s more than a wave—it’s a tsunami of transactions driven by business owners reaching retirement age.
That trend is only beginning to build.
We’ve also come through a period of extraordinary uncertainty. In just the last few years, business owners have navigated COVID, supply chain disruptions, significant inflation, sharp increases in interest rates, election uncertainty, immigration concerns, tariffs, geopolitical tensions, and whatever challenge comes next.
The only certainty today is uncertainty.
As a result, many owners are asking themselves whether now is the right time to make a move.
What we find in the middle market is that businesses are often less volatile and less sensitive to global events than people assume. Many of the companies we work with have little or no debt, so rising interest rates may not affect them as much as headlines suggest.
Ultimately, though, the decision is often less about economic conditions and more about the emotional question every owner faces:
Is now the right time?
Building Value Through Leadership
Kevin Leahy: Ramsey, when you tell that story, are those outcomes driven by external circumstances, or are they driven by choices the owner made internally?
Could the outcome have been different?
One thing we’ve seen over time is that a larger percentage of our clients are business owners, which is part of the reason we’re having these conversations today. As we’ve grown our own business and dealt with many of the same challenges our clients face, we’ve learned that you need to spend time thinking strategically. You can’t just focus on getting from Monday to Tuesday. You have to think about next Friday, next year, and what comes after that.
So, to come back to my question: If someone really wanted to pass the business to the next generation, or if they wanted to sell internally to a management team, could they have changed the outcome through planning?
Ramsey Goodrich: Absolutely.
It all starts with defining success.
There’s always a balance between liquidity—whether that’s proceeds from a sale or a private equity partnership—and other objectives. Passing a business to family often doesn’t create the same liquidity event. Selling to a management team may be highly rewarding, but it may also result in a lower valuation than a competitive market process.
So the first step is understanding the objectives.
What are the personal goals? What are the financial goals? What are the legacy or altruistic goals?
For some companies, an ESOP can be an outstanding solution. The tax advantages can be significant, but it isn’t the right fit for everyone.
The same is true of a sale or a private equity partnership. There is no universal answer. Everything depends on the owner’s definition of success and the desired outcome.
Kevin Leahy: Is it also fair to say that if you’re committed to maintaining an independent business, you’re likely investing more time, energy, and money into building a management team?
And if your plans eventually change, doesn’t that investment also increase the value of the company to an outside buyer? A well-run business with a management team that can operate independently of the founder is probably more attractive than one that’s dependent on a single individual.
Ramsey Goodrich: Absolutely.
Your management team is one of the best predictors of value.
People don’t invest in businesses because of the equipment, the building, or even the brand. They invest because of the people running the company and the team that will continue driving it forward.
One of the biggest risks we see in founder-led and family-owned businesses is concentration risk.
Value is the inverse of risk. The riskier a business is, the less someone is willing to pay for it.
When one person is making all the decisions, holding all the relationships, and carrying all the institutional knowledge, that’s a significant risk—not only for the company, but for the next owner or partner.
What happens if that person disappears tomorrow?
We used to say, “What if they get hit by a bus?” Then we actually had a client get hit by a car, so now we joke about being abducted by aliens instead.
But the point remains the same.
If all of that knowledge and decision-making authority is concentrated in one person, the business becomes far riskier. That’s why investing in management is one of the best investments an owner can make.
Whether you’re planning a transition to family, management, an ESOP, private equity, a family office, or another buyer, strengthening your leadership team creates value.
The flip side is something I often joke about with family businesses:
Fire your brother-in-law.
Nobody likes him anyway.
Now, I’m only half kidding.
Too often, owners keep underperforming family members in the business because it’s easier than dealing with the situation. But all you’re really doing is passing that problem on to the next owner.
The next owner is going to address it anyway.
In some cases, the best move is to have an honest conversation, compensate them fairly, and help them move on to their next opportunity.
Beyond improving operations, there’s often a valuation benefit as well. If someone is being paid a substantial salary but isn’t contributing meaningful value, that expense can become an add-back when the business is valued. As a result, removing that cost can improve profitability and ultimately increase enterprise value.
More importantly, it improves the organization, strengthens the management team, and makes the company healthier going forward.
Kevin Leahy: Let me ask about the opposite situation.
In smaller companies, we often hear owners say, “We know we probably need a CFO, but we can’t afford one.”
They’re viewing that role as an expense rather than an investment. Using the same logic, couldn’t someone argue that hiring a highly compensated executive reduces profitability and therefore reduces value unless that person truly moves the needle?
Ramsey Goodrich: That’s the wrong way to think about it.
You can’t view everything as an expense. You have to view it as an investment in future success.
Find the right person. Pay them well. If they’re the right hire, they’ll create far more value than they cost.
One of the things we look for in prospective clients is their willingness to invest in their success.
Have they invested in management?
Are they willing to complete a quality of earnings report?
Are they willing to upgrade advisors when necessary?
Have they spent time on estate planning, wealth planning, and the other foundational elements that support a successful transition?
The owners who invest in building a stronger business consistently achieve better outcomes.
When business owners make those investments ahead of time, the results can be remarkable.
Tiptoe to the Starting Line
Denis Horrigan: Ramsey, you’ve done hundreds of transactions, correct?
Ramsey Goodrich: Yes.
As a firm, we’ve completed roughly 450 transactions. Personally, I’ve worked on about 120 to 130.
Denis Horrigan: You have a lot of stories, which I love.
Can you think of an example where a business owner really did the preparation work and did it well?
Ramsey Goodrich: This may sound self-serving, but it’s not meant to be.
Many of our clients succeed because we spend a lot of time upfront asking a simple question: Are we actually ready?
Most business owners want to know how quickly we can get them to market and how quickly we can get them an offer. The problem is that they’re sprinting to the starting line.
When that happens, they often trip on the way to the finish line.
The better approach is to slow down and prepare properly.
Think about what happens at closing. You’re sitting there with your Connecticut Wealth Management pen, signing hundreds of pages of documents. If your hand is shaking and you’re wondering, Am I doing the right thing? Do I have enough money? Is this the right partner? Is my family ready? Is my management team ready?—then you probably shouldn’t be doing the deal.
No matter how attractive the purchase price may be, if you’re questioning the decision at the closing table, there’s a good chance you’ll regret it later.
Statistically speaking, many business owners do regret selling their businesses.
The difference for our clients is that we spend so much time on planning and preparation before ever going to market.
We don’t sprint to the starting line.
We tiptoe to the starting line.
Sometimes that process takes months. Sometimes it takes years.
One of our best outcomes involved a fifth-generation family business. We spent 13 years cultivating the relationship, helping the family work through multigenerational issues, make strategic acquisitions, streamline operations, and develop a long-term vision before we ever discussed going to market.
I had another situation where we’d been talking with a family for years. The father always said, “No, no, no. We’re not selling.”
Meanwhile, I’d occasionally get calls from the next generation asking, “Can we go yet? Are we ready?”
Then one Wednesday I got a phone call.
“Dad said yes. Dad said yes.”
I said, “What do you mean Dad said yes?”
“He said we can sell the business. Let’s go. How quickly can we get started?”
That conversation captured just how much emotion is involved in these decisions.
At the end of the day, planning, preparation, and thoughtful consideration of the desired outcome are among the strongest predictors of success in any transaction.
Kevin Leahy: Denis, did you write that down?
“Sprinting to the starting line.”
Denis Horrigan: Actually, I wrote down, “Don’t sprint to the starting line. Tiptoe to the starting line.”
Ramsey Goodrich: Exactly.
Tiptoe to the starting line, then sprint to the finish.
Once you’ve done the planning and preparation and you’re ready to make that first call, it’s game on.
At that point, time is not your friend.
You want to move efficiently through the process and get to closing.
But before that first call, there are a lot of pieces that need to be in place.
There’s due diligence preparation. There’s personal financial planning. There’s trust and estate planning. There’s wealth management planning. There’s management succession planning.
All of those elements contribute to a successful transaction.
So take your time getting ready.
But once you’re ready, make the call and sprint to the finish line.
Responding to Unsolicited Interest with Discipline, Not Emotion
Denis Horrigan: Ramsey, there are so many unsolicited offers happening right now. Business owners receive emails, phone calls, and text messages from random sources every day.
Someone who may never have considered selling their business suddenly gets a call expressing interest in an acquisition.
Should business owners be taking those calls? Should they respond to those emails and texts, or should they ignore them?
And when does it make sense to engage an investment banker like you?
Ramsey Goodrich: That’s a great question.
The short answer is: keep a file of them.
Ninety-nine percent of those messages are worthless. Many are AI-generated. I probably receive seven or eight a day myself.
“Hey, we have a buyer interested in your business.”
“Hey, we’re an investment bank. We’d love to help.”
Apparently they didn’t bother to look at what I do for a living.
Most of those messages can be ignored. But every once in a while, something stands out. It might be a unique approach, a compelling rationale, or a genuinely strategic buyer.
When that happens, save it.
I wouldn’t necessarily engage right away, but keep a record of the interest. If that organization has demonstrated a genuine desire to acquire your company, they may belong on a future shortlist of potential partners.
But before you respond, you have to answer a more important question:
Why?
What are you actually trying to accomplish?
Getting an unsolicited offer is flattering. It’s easy to think, “My business must be incredibly valuable. Everyone wants to buy it.”
That feeling usually lasts until someone starts digging into the details.
That’s why preparation matters.
And my number one rule is simple:
Do not send your financial statements.
The first thing many buyers ask for is financial information. Resist the temptation.
Most business owners manage their income statements with taxes in mind. They’re often focused on minimizing taxable income. That’s perfectly reasonable, but it’s not the lens through which you want a buyer evaluating your business.
You want buyers looking at the highest sustainable earnings profile, not the lowest taxable one.
If you send financials too early, you’re almost guaranteeing yourself a mediocre offer.
The second issue is valuation.
Just because someone knocks on your door doesn’t mean you’re receiving the best offer available.
When we take a company to market, we’ll typically approach 50 to 100 potential partners. From that process, we may receive 10, 12, or even 15 indications of interest.
The range in valuation can be enormous.
On one transaction we’re working on right now, the highest offer is literally double the lowest offer.
Typically, we see a spread of 20% to 30% between the low and high bidders. This particular situation happens to be an extreme example, but it illustrates the point.
If someone makes you an unsolicited offer, how do you know where it falls on that spectrum?
Is it the highest offer? The lowest offer? Somewhere in the middle?
You don’t know.
So when someone expresses interest, thank them for reaching out. Then step back and ask whether this is the right time for you and whether selling aligns with your goals.
Once you’ve answered those questions, assemble the team.
Start with your wealth manager and your trust and estate planning professionals. Bring in your accountant and investment banker. Then involve your attorney to help structure and document the transaction.
Kevin Leahy: When is it too early?
Let’s say someone believes they may want to sell five years from now. Maybe it’s ten years from now.
Is there such a thing as starting too early?
I would imagine that someone who does as many transactions as you and your team do is always going to have ideas about how owners can improve the business and better prepare for an eventual transition.
Is that fair?
Ramsey Goodrich: Never.
There is no such thing as too early.
If you talk to entrepreneur coaches or founders building businesses from scratch, many will tell you that a business should be built to sell.
That doesn’t mean you have to sell it. It simply means you should be prepared if the opportunity arises.
So when is too early?
Arguably, it’s already too late because you didn’t start planning the day you founded the company.
The reality is that middle-market businesses aren’t usually as volatile as public companies. Most owners don’t need to rush into a transaction because of short-term market conditions.
In fact, we advise more people to delay going to market than we advise to move forward.
Right now, we probably have 10, 15, maybe 20 companies in our pipeline where we’re saying:
“Go fix this issue.”
“Address that risk.”
“Strengthen this part of the business.”
Then come back when you’re ready.
Rushing to market because someone knocked on your door—or because you had a bad day at the office—is usually the wrong answer.
The right answer is discipline.
Be thoughtful. Be intentional. Commit to your own success.
Denis Horrigan: I think that’s an important point about unsolicited offers.
Owners will often say, “That person was great. They were so nice. We really connected.”
And my response is usually:
Of course you did.
They’re a salesperson.
Ramsey Goodrich: Exactly. That’s their job.
Denis Horrigan: Their job is to build rapport and generate interest.
That doesn’t necessarily mean the firm they represent is the right fit for your company just because they’re enjoyable to have a cocktail with or spend an afternoon on the golf course with.
Ramsey Goodrich: And just because an offer sounds attractive doesn’t mean it actually is.
It’s only a starting point.
If a buyer knows nothing more than, “This company has $50 million in revenue and $5 million in EBITDA,” they might say, “Great. We’ll pay six times EBITDA.”
Suddenly, you’re looking at a $30 million valuation and thinking, “That sounds pretty good.”
But you haven’t addressed any of the risks.
You haven’t highlighted the opportunities.
You haven’t normalized the financial statements.
Maybe that $5 million of EBITDA is actually $7.5 million once the business is properly positioned and adjusted.
Maybe a competitive process would generate a seven- or eight-times multiple instead of six.
The point is that evaluating an offer in a vacuum rarely makes sense.
Planning, preparation, and process are what create better outcomes.
The Anatomy of a Successful Transaction
Kevin Leahy: What defines a smooth transaction? And I apologize for using the word deal, but what makes a transaction go smoothly versus becoming difficult?
Ramsey Goodrich: There are a few ways to answer that.
First and foremost, the biggest predictor of success is a genuine commitment from the owner to actually complete the transaction.
We were talking earlier about whether owners should “test the market.” My answer is almost always no.
Testing the market is usually a fool’s errand.
A successful transaction requires three things:
First, the owner has to be ready.
Second, the business has to be ready.
Third, the market has to be ready.
When someone tests the market, they’re only evaluating one of those three variables. It doesn’t tell you whether the owner is emotionally prepared, whether the business is positioned for success, or whether the timing is right.
That’s why we love working with motivated owners—people who have clarity about what they’re trying to accomplish and who believe there’s something better waiting for them on the other side of the transition.
That commitment matters.
The second major factor is preparation.
We keep coming back to planning and preparation because they truly make a difference.
The planning side starts with personal financial planning. Is the transaction going to provide enough resources to accomplish your goals? Will it support the life you want to live after the sale?
Preparation is about getting ahead of the inevitable due diligence process.
Every business has risks. Every business has vulnerabilities.
You don’t need to solve every issue, but you should address as many as possible before going to market. The more prepared you are, the smoother the process tends to be.
The third factor is having a great team of advisors.
M&A is a team sport.
Nobody should go through it alone.
We often talk about what we call the Core Four—the four key advisors every business owner should have in place before pursuing a transaction.
The first is a wealth manager.
You need someone helping you answer questions such as: Is this enough? How should the proceeds be structured? What are the trust and estate planning implications? How do I take care of my family, my community, and my philanthropic goals?
The second is a strong accounting firm.
They help evaluate profitability, identify add-backs and adjustments, assess growth opportunities, and structure the transaction from a tax perspective.
At the end of the day, what matters isn’t the headline number—it’s what actually ends up in your bank account after taxes.
The third is an experienced M&A attorney.
And I always emphasize M&A attorney.
Dentists and brain surgeons both use drills. They both went to medical school. They both have excellent reputations and glowing reviews.
But you wouldn’t ask your dentist to perform brain surgery.
The same principle applies here.
Don’t use your divorce attorney to handle your M&A transaction. Hire the right specialist for the job.
And finally—and yes, this part is somewhat self-serving—you need a good investment banker.
Industry expertise matters, but it’s not everything.
More important is finding someone who understands your objectives, gives honest advice, and is focused on achieving the best possible outcome for you.
One question we often get during pitches is, “How well do you know the buyers?”
We’re actually very proud of our answer.
Across roughly 450 transactions completed by Carter Morse & Goodrich, we’ve never sold two companies to the same buyer.
Think about that for a moment.
We operate in a relatively narrow set of industries, yet we’ve worked with 450 different buyers across 450 different engagements.
To me, that’s important because it reinforces who we’re working for.
If an investment banker repeatedly sells businesses to the same handful of buyers, you have to ask whether they’re optimizing for the client or protecting a relationship with a preferred buyer.
Our responsibility is to find the best outcome for the owner.
So when you’re building your advisory team, make sure you have an investment banker whose interests are aligned with yours and who is focused on helping you achieve your definition of success.
Management, Opportunity, and the Right Partner Fit
Kevin Leahy: Let’s go back to the management team for a moment.
An owner, founder, or CEO can’t possibly keep a transaction entirely to themselves, right?
Talk a little about how management becomes involved in the process and why they’re so important.
Ramsey Goodrich: Many owners try to keep it to themselves.
But management is absolutely critical.
One of the biggest questions in any transaction is when to bring management under the tent. Once an owner decides to pursue a transaction, that conversation with the management team is often the second-scariest conversation they’ll have.
It’s emotional. It’s difficult. But it can also be well planned and well executed.
The reality is that M&A is hard. It’s essentially a second full-time job for a year or more.
Even after all the planning and preparation, completing a transaction requires an enormous amount of work. No owner can realistically do it alone while continuing to run the business.
That’s why management has to be involved.
As investment bankers, our job is to understand the business well enough to position it effectively, create marketing materials, and communicate the opportunity to potential investors or partners.
We can’t get that understanding from a single person.
Every leader sees the business differently.
When we bring management into the process, we often discover perspectives the owner doesn’t see.
The head of operations may have a very different view of what’s happening on the shop floor.
The head of sales may say, “I know exactly how we could grow, but we’ve never had the resources.”
The finance leader may explain that certain processes exist simply because that’s how the owner prefers to operate.
None of those perspectives are necessarily right or wrong. But together, they help paint a much more complete picture of the business.
They also help us identify the right partner.
If valuation is the inverse of risk, then demonstrating a strong management team reduces risk.
When buyers see a deep bench of capable leaders who understand the opportunities ahead and are ready to execute, the business becomes significantly more valuable.
In many cases, management sees growth opportunities that the owner hasn’t pursued—not because they’re bad ideas, but because the owner’s perspective on risk is different.
For many founders, the business is their life’s work and their primary source of wealth.
They understandably think, “This is my nest egg. I can’t afford to take unnecessary risks.”
A private equity firm, on the other hand, may have a very different perspective. Their job is to deploy capital, hire talent, make acquisitions, and accelerate growth.
So when management can clearly articulate those opportunities, and we can present them to the right partner, value often increases.
Kevin Leahy: I think I’ve heard you say this before: sometimes buyers actually like seeing a business that’s less than perfect because those imperfections represent opportunities.
Is that fair?
Ramsey Goodrich: Absolutely.
Owners need to be willing to be thoughtful, transparent, and vulnerable enough to admit that their business isn’t perfect.
The reason is simple: different partners bring different strengths.
Let’s use private equity as an example.
Years ago, when I was running the Financial Sponsors Group, our coverage universe consisted of about 53 middle-market private equity firms.
Today, there are thousands of private equity funds with trillions of dollars available to invest.
The industry has become incredibly specialized.
A firm that focuses on manufacturing may never look at a healthcare company. A healthcare-focused investor may never consider a manufacturing business.
The pool narrows very quickly.
Then you start looking at what each buyer does best.
If your biggest challenge is sales, why would you partner with an investor whose expertise is operational efficiency? You should be looking for a partner who knows how to accelerate revenue growth.
If your opportunity is organic growth, why partner with someone whose entire strategy revolves around acquisitions?
The goal is to find the right fit.
That’s why being honest about weaknesses is so important.
In fact, I don’t really think of them as weaknesses.
I think of them as opportunities.
There is no such thing as a weakness—only an opportunity for the next partner to do better.
Denis Horrigan: I’m writing that one down.
Ramsey Goodrich: You should.
Because that’s where the magic starts to happen.
When owners are transparent about both the strengths and opportunities within the business, they’re much more likely to find the right partner.
And that’s where we come full circle to the question we’ve been discussing throughout this conversation:
What does the owner want to do after the transaction?
Sometimes owners discover a partner who can provide capital, resources, expertise, and growth opportunities they could never access on their own.
Suddenly they’re saying, “Wait a second—we could do that? That’s exciting. I’d actually like to stay involved.”
That’s why finding the right partner matters so much.
When the fit is right, everyone becomes more excited about the future.
What Really Happens to Employees in a Business Sale
Denis Horrigan: Along those lines, Ramsey, many business owners—especially founders and family-owned businesses—feel a deep sense of loyalty to the employees who helped them build the company.
One of the biggest concerns we hear is, “If I sell the business, what’s going to happen to my team? Are they going to fire everyone?”
How do you help owners work through that fear?
Ramsey Goodrich: In my experience, that’s largely a false narrative.
When people hear about acquisitions, they often assume layoffs are inevitable. In the middle market, that’s rarely what we see.
Large public-company acquisitions can be a different story. But in the middle market, buyers are typically investing because they see growth opportunities.
Across roughly 450 transactions as a firm—and more than 120 that I’ve personally worked on—I have almost never seen management teams terminated at closing unless that was the individual’s choice.
In fact, it’s usually the opposite.
Buyers invest in people.
They provide additional resources, expertise, specialization, and growth opportunities. They want the existing team to succeed because that’s how they create value.
There are exceptions.
If an owner has already stepped away from day-to-day operations and simply wants to cash out, that’s a different situation. We have a client right now where the owner told us, “I haven’t been involved in years. Write me a check and I’m gone.”
In that case, management was thrilled because they were already running the business.
But generally speaking, buyers aren’t looking to dismantle teams.
The one area that can be more vulnerable over time is the CFO role.
Private equity-backed businesses often require a different level of financial reporting, lender communication, strategic planning, and operational analysis than many privately held companies are accustomed to.
As a result, CFO expectations can change significantly after a transaction.
But outside of that, we rarely see widespread turnover.
Denis Horrigan: Kevin was asking earlier about involving management in the process.
How do you balance that with confidentiality?
If an owner decides to explore a transaction, they don’t necessarily want rumors spreading throughout the company.
How do you manage that risk?
Ramsey Goodrich: There are risks, but there are also opportunities.
We’re currently working with a company in Denver that was extremely hesitant to bring management into the process. After years of discussion, we finally convinced the owner to involve a small group of key leaders.
Not only did it help us better understand the business, but something unexpected happened.
The owner later told us, “Thank God you convinced me to do that. My management team is finally thinking like owners.”
They started identifying new growth opportunities, operational improvements, cost savings, and strategic initiatives.
The owner’s reaction was, “Why didn’t I bring them in sooner?”
That’s one of the hidden benefits of involving management. They’re no longer just employees—they become part of the solution.
Typically, we recommend bringing in a small group of key leaders: the head of sales, the head of operations, the CFO, and perhaps one or two others depending on the organization.
To protect confidentiality, we often create incentive arrangements tied to the transaction. In exchange for maintaining confidentiality and supporting the process, key leaders may receive a bonus at closing and additional incentives tied to remaining with the company after the transaction.
That structure benefits everyone.
The seller gains confidence that the management team will remain engaged through the process.
The buyer gains confidence that key leaders aren’t going anywhere immediately after closing.
It’s one of the most effective tools available.
Kevin Leahy: And that’s something your team helps structure?
Ramsey Goodrich: Absolutely.
The legal documentation is handled with counsel, but we help owners think through the approach.
One of the first questions we get is, “How much should I pay?”
The truth is there isn’t one right answer.
We’ve seen flat-dollar bonuses. We’ve seen percentages of salary. We’ve seen formulas tied to transaction value.
The right answer is whatever feels meaningful and appropriate for the individuals involved.
Kevin Leahy: Is it common for owners to come into the process already knowing they want to do something for their team?
Ramsey Goodrich: Almost always.
Most owners don’t necessarily know the exact amount, but they know they want to recognize the people who helped them build the business.
One of the most memorable closing dinners I’ve ever attended involved a highly specialized welding company in Georgia.
The owner sold the business for significantly more than he ever expected. At the closing celebration, he gathered ten or twelve key employees and their spouses.
These were hardworking people who had spent years helping build the company.
He stood up and said, “This isn’t my business. It’s our business. We’re entering a new partnership, and I couldn’t have done it without you.”
Then he told everyone to look under their chairs.
Taped beneath each chair was a check for one million dollars.
It was one of the most emotional moments I’ve ever witnessed.
Watching people realize that their lives had changed because of the success they helped create was incredibly powerful.
We had another transaction where 22 members of management already owned equity in the company. When we partnered with a private equity firm, that ownership expanded.
Forty-seven employees became owners of the business going forward.
Not symbolically—meaningfully.
When people have that level of participation and ownership, the impact can be extraordinary.
That’s why these conversations matter.
They can be difficult to start, but they often lead to some of the most rewarding outcomes of the entire process.
Kevin Leahy: I imagine it’s easier when the numbers are large enough.
When the economics are tighter, those decisions probably become more difficult.
Ramsey Goodrich: They do.
But what we’ve found is that it’s still usually the right thing to do.
For many owners, it’s a way of saying:
“Thank you for helping me get here.”
“Congratulations on what we’ve built together.”
“And here’s an opportunity to participate in what comes next.”
That’s a powerful message, and it often sets the stage for future success.
Choosing the Right Partner Over the Highest Bid
Kevin Leahy: Ramsey, going back to something you mentioned earlier about defining the desired outcome, I think many business owners struggle with the fact that their business becomes part of their identity.
Honestly, I think Denis and I probably see it in ourselves, and I’m sure you do as well.
Whether you’re a business owner, an attorney, a physician, or a restaurateur, people begin to know you by what you do.
How much does that factor into the conversations you have with owners who are looking back on a long career and considering a transition?
Ramsey Goodrich: Without question, it matters.
That’s where legacy becomes incredibly important.
We’re fortunate to work with many successful businesses that have been around for generations. In most cases, money is important, but it’s not the driving factor.
If someone has already built a successful company and is taking home significant income every year, the decision often isn’t about maximizing one more dollar.
At that point, it stops being a scorecard.
Instead, owners start asking different questions.
What happens to the company?
What happens to the employees?
What happens to the community?
What happens to everything I’ve spent decades building?
Legacy becomes the primary consideration.
I worked with a manufacturing company here in Connecticut where the owner’s only non-negotiable requirement was simple:
“You can never move the factory.”
Naturally, we asked why.
From a business standpoint, the location wasn’t ideal. Labor was difficult to find. Transportation was challenging. Shipping costs were higher than in other markets.
On paper, there were plenty of reasons someone might want to relocate.
But her answer had nothing to do with logistics.
She said, “Because my shift supervisor’s wife runs the diner next door. Because my controller’s husband is the town postmaster. Because one of our factory workers’ spouses owns the nail salon.”
Then she said something I’ll never forget:
“If this factory goes away, the town goes away.”
For her, the business wasn’t just a manufacturing company.
It was part of the community’s identity.
The factory and the town were intertwined.
Kevin Leahy: I feel like I saw that in a Hallmark movie.
Ramsey Goodrich: It sounds like one, but it was real.
It was a multigenerational family business, and ultimately we found a multinational buyer that needed a manufacturing footprint in the United States.
They understood the importance of the location and were fully committed to keeping the facility where it was.
And yes, we turned down higher offers to achieve that outcome.
Denis Horrigan: Does that happen often?
Do owners regularly decide not to take the highest offer?
Ramsey Goodrich: Don’t tell anyone.
Maybe we should cut this from the podcast.
But here’s the secret:
Nobody takes the highest offer.
Now, if there’s only one offer, that’s a different situation.
But if you’ve followed a disciplined process, identified the right potential partners, and made it to the finish line with several strong options, the decision is rarely just about price.
By that point, the conversation becomes much broader.
Who’s going to take care of the employees?
Who’s going to protect the culture?
Who’s going to preserve the legacy?
Who’s going to create opportunities for management?
Who’s going to do the right thing?
When owners have multiple attractive options, those factors often matter just as much as valuation.
And in many cases, they matter more.
Because for most founders and family business owners, the company is far more than a financial asset.
It’s a reflection of who they are, what they’ve built, and the impact they’ve had on the people around them.
That’s why finding the right partner—not simply the highest bidder—is often the ultimate definition of success.
Clarity, Commitment, and the First Step Toward an Exit
Denis Horrigan: Ramsey, we literally could talk all day. This is awesome stuff. You talk about the team and how important it is to put together the right team. We’re super grateful for the opportunity to be part of your team and for all the things you’ve done for our business owner clients.
Seriously, it’s an honor to get the chance to work with you.
I’m going to ask you one final question. As we say, everyone exits—everyone transitions out of their business eventually. If a business owner is watching this and has stuck around to the end, what’s the one thing you’d like them to take away? What’s the first step they can take right now to prepare for the day they eventually leave their business?
Ramsey Goodrich: Great question. And thank you for preparing me for it, because I really thought long and hard about my answer.
Be honest with yourself about why you’re considering a transaction. Not how, not when, not any of the other details—why.
When you truly understand the why, all the other pieces start to fall into place.
Is it because you want to get out? Is it because you want to transition? Is it for your family? Is it for philanthropy? What does success actually look like for you?
Start by defining success and understanding your motivation. Then make a real commitment to pursuing it. It may still take three, four, or more years to reach the outcome you want, but everything begins with understanding what success means to you.
Denis Horrigan: That’s awesome. Great advice.
Thank you so much. This has been a lot of fun. As I said, we could do this all day, but you do have a business to run.
Ramsey Goodrich: Was that an hour already? We’re only about halfway through our agenda. Sorry for talking so much.
Denis Horrigan: No, no. It’s been great.
Kevin Leahy: Absolutely. Ramsey, you’re a gentleman and a scholar.
Ramsey Goodrich: Don’t tell anybody. You’ll ruin my reputation.
Denis Horrigan: It’ll be our secret. Besides, nobody’s listening anyway.
Ramsey Goodrich: Thanks, Mom.
Kevin Leahy: Mom, the handsome man is Ramsey. His name is Ramsey.
Denis Horrigan: And no, you can’t have his number.
Ramsey Goodrich: Gentlemen, thank you. It’s an honor and a privilege to spend time with you and have these conversations.
We love helping business owners think through and approach what is often a once-in-a-lifetime opportunity with discipline and intention.
As we like to say, if you’re only going to do this once in your lifetime, do it right the first time. Take the time to understand why, who, and how.
Denis Horrigan: Awesome. Perfect way to end.
Kevin Leahy: Truly fun.
Ramsey Goodrich: Excellent.
Denis Horrigan: All right. Thanks, everyone. We’ll see you next time.