Why 95% of business owners attempt the most complex financial transaction of their lives essentially alone… and what the other 5% know.

THE THREE-SENTENCE SUMMARY

• Selling a $5M to $50M business well requires four specialized chairs at the table, not two.
• Most owners build the team too late, and they pay for that with discounted valuations, broken deals, and post-closing regret.
• The 5% who get this right do not assemble the team after they decide to sell. They build it 12 to 36 months before.

Only 5% of Baby Boomer business owners have assembled a full advisory team to guide them through the exit process. Five percent. That means 95% of owners are attempting the most complex financial transaction of their lives essentially alone.

There is a version of this conversation I have had many times. A founder I have known for years calls me. He has just received an unsolicited offer for his business… somewhere in the $20 to $30 million range, give or take. He has built the company over three decades. He has a CPA he has used since the early years. He has a personal attorney who handled his estate. And when I ask him who is going to quarterback this transaction, he looks at me and says some version of: “What do you mean? I’ve got my CPA and my attorney. That’s the team.”

It isn’t. And the gap between what he has and what he needs is about to cost him, in my experience, somewhere between fifteen and twenty-five percent of the deal value… assuming the deal closes at all.

This is the part of the exit journey that almost nobody talks about until it’s too late. Not the valuation. Not the deal structure. Not the diligence horror stories. The team. The orchestrated, integrated, deal-tested group of professionals who actually know how to navigate a once-in-a-lifetime transaction together.

Most owners don’t have one. Most owners don’t know they need one. And by the time they figure it out, the deal is already in motion and the leverage has shifted to the buyer.

The Four Chairs That Must Be Filled

There are four roles that need to be sitting at the table when you sell your business. Not three. Not two. Four. And each one does something the others cannot.

The first chair is your CPA or tax advisor. And here’s where the first big mistake happens, because the CPA who has done your books for twenty years may not be the right person to handle a transaction. Day-to-day accounting and transaction tax work are different specialties. The CPA you need at the table understands quality of earnings analyses, working capital adjustments, the difference between an asset sale and a stock sale, the tax implications of an earnout structure, and how to defend your financial statements when a buyer’s diligence team starts taking them apart line by line. If your current accountant has never done that work, you need a transaction CPA alongside them. Not instead of them. Alongside.

The second chair is an M&A attorney. Not your business attorney. Not your estate attorney. Not the lawyer who handled your divorce or your real estate closing. An M&A attorney whose practice is built around transactions of your size and type.

You want a deal maker, not a deal breaker. There is a difference, and any owner who has watched an over-zealous attorney kill a good deal over the wrong points knows exactly what it is.

The definitive agreement that gets signed at closing is the contract that defines the rest of your life… earnout terms, non-compete scope, indemnification provisions, representations and warranties that survive closing. The wrong attorney in this chair doesn’t just cost you money. They cost you years of post-closing freedom.

The third chair is an investment banker or business broker, depending on the size and complexity of your business. For a company doing $5 million to $15 million, a quality M&A broker is usually the right fit. Above $15 million, you typically want a lower-middle-market investment bank. Their job is to run the process… identify and qualify buyers, manage the bidding dynamic, create competitive tension, and protect you from the half-dozen ways a buyer will try to chip away at price and terms once they think they have you cornered. A founder running the process alone is almost always negotiating against a buyer’s professional deal team. Those are not even odds.

The fourth chair is the one that almost nobody fills, and it is the one that matters most. Call it the strategic coach. Call it the integrative advisor. Call it the quarterback. The name matters less than the function. This is the person who sees the whole picture across all three readiness dimensions… business, financial, and personal… and who orchestrates the other three professionals so they’re actually working together instead of working in parallel.

Four chairs. Four specialties. One team. The math doesn’t change based on how good any one of them is.

Why You Resist Building the Team

If the four-chair model is so clearly the right answer, why do so few owners actually build it? In my experience, three reasons come up over and over. As you read them, notice which one is yours.

The first reason is cost. Investment banker fees in particular cause something close to a physical reaction in most founders. A success fee of five or six percent on a $20 million deal is $1 million to $1.2 million in transaction costs, and your entrepreneurial instinct is to recoil from that number. I have watched owners try to talk themselves into selling without a banker to save the fee, then leave three or four times that amount on the table in price and terms because they had no leverage in the process. The math is not subtle. Bankers, properly engaged, almost always pay for themselves several times over. The cost is real. The cost of not having one is usually larger.

The second reason is your belief that the existing professional relationships will be sufficient. “My CPA can handle it.” “My attorney has been with me for twenty years.” This is loyalty, and loyalty is admirable, and it is the wrong frame for the biggest deal of your life. The question is not whether your current advisors are good people who have served you well. The question is whether they have done this specific kind of work, on a deal of this specific size and structure, often enough to know where the landmines are. If the answer is no… and for most general practitioners it is no… they need to either expand the team or step aside for it.

The third reason is your instinct to do everything yourself. The same instinct that built the business in the first place. The same instinct that survived the bad years, the cash crunches, the personnel disasters, the moments when nobody else believed it would work. That instinct is a feature, not a bug, for most of your career. And it becomes a liability in the exit process, because the exit is not a problem you can grind your way through with longer hours and harder work. It is a specialized transaction that rewards specialized expertise.

Marshall Goldsmith’s title says it directly. What got you here won’t get you there.

The Quarterback Problem

Here’s what happens when an owner assembles a competent CPA, a competent attorney, and a competent banker, but doesn’t have a quarterback. Each professional does excellent work inside their lane. The CPA gets the tax structure right. The attorney negotiates the legal documents with skill. The banker runs a credible process and brings in qualified buyers. And the deal still goes sideways. Why?

Because nobody is integrating the work.

The banker is optimizing for purchase price. The attorney is optimizing for legal protection. The CPA is optimizing for tax efficiency. Each one is doing their job. And you… the only person in the room with the full picture of your life… are trying to evaluate a deal across all three dimensions while simultaneously running the business, managing employee anxiety, and processing the emotional weight of selling something you built from nothing. Most owners are not equipped to be the quarterback of their own deal. Not because they aren’t smart enough. Because they are inside it.

This is what I do as the integrative advisor on transactions. I’m not the tax expert. I’m not the legal expert. I’m not running the buyer process. I’m the person who makes sure the tax structure, the legal protections, the deal terms, the family conversations, the post-closing plan, and the founder’s actual life are all pointing in the same direction. I challenge the banker when the headline price is masking a problematic structure. I push the attorney when the legal protections are stripping value the banker just created. I tell the founder the truth when they’re about to make a decision they will regret for the rest of their life because they’re exhausted and just want it to be over.

The quarterback is the person who has been in the room before, who is not negotiating against you on fees or scope, and whose only job is to make sure the team is actually a team.

This is the function that the existing advisory ecosystem does not provide on its own. CEOIQ® Renaissance is built around it.

When to Start Assembling

The single most common mistake I see is owners assembling the team after they have already decided to sell. By that point, the work the team needs to do is compressed into a window that doesn’t allow it to be done well.

Value enhancement work… cleaning up the financials, documenting the processes, building the leadership bench, reducing customer concentration, removing the owner from daily operations… is most of what determines if a buyer pays a premium multiple or a discounted one. That work takes 12 to 36 months. The transaction CPA needs to see your books 18 months before you go to market, not three months before, because the cleanup of a decade of casual bookkeeping is not a weekend project. The attorney needs to review your contracts, your employment agreements, your intellectual property documentation, and your corporate housekeeping long before a buyer’s diligence team gets to them. The banker needs to understand your business deeply enough to position it correctly to the right buyers, which means engaging them before the buyer list matters.

And your quarterback needs to be on your team first, because the question of whether you are ready to sell at all… business, financial, and personal… has to be answered before the rest of the team can do its work productively.

The founders I described at the start… the ones with the longtime CPA, the personal attorney, and the unsolicited offer? Most of them did eventually assemble the full team. Some did it in time, and the deal closed at full value. Many did it too late, and the buyer used the late assembly against them in negotiation. I have watched founders leave fifteen to twenty-five percent of the deal value on the table because the team came together three months before closing instead of twelve to thirty-six months before going to market. That is not a small amount of money. It is, in some cases, the difference between the retirement they planned and the one they had to settle for.

Late assembly means rushed decisions, missed opportunities, and a process that runs the owner instead of the owner running the process. Early assembly means the deal gets done on your terms, on your timeline, with the protections that matter to your actual life on the other side of closing.

The 5% of owners who get this right are not smarter than the other 95%. They started earlier. They built the team before they needed it. And when the moment came, they were not assembling the team and running the process at the same time. They were just running the process.

Key Takeaways

• There are four chairs at the exit table: a transaction CPA, an M&A attorney, an investment banker or M&A broker, and an integrative advisor or quarterback. All four matter. Three out of four is not enough.
• Loyalty to long-tenured advisors is admirable and it is the wrong frame for choosing your deal team. The question is whether they have done this specific work on a deal of this specific size, often enough to know where the landmines are.
• A competent team without a quarterback still produces deals that go sideways, because each professional optimizes their own lane and nobody integrates the work across all three readiness dimensions.
• Investment banker fees feel large until you’ve watched an unrepresented founder leave three to four times the fee on the table in price and terms. Properly engaged, bankers pay for themselves several times over.
• Assemble the team 12 to 36 months before you go to market, not three months before. Late assembly compresses the work that determines whether you sell at a premium or at a discount.

Where to Start

Building your advisory team begins with knowing what kind of help you actually need… and where the gaps in your current setup actually are. The CEOIQ® Renaissance Executive Briefing walks through the readiness framework that puts the team conversation in the right context. You can register at ceoiq.us.

If you are already in conversations with a potential buyer, or already feeling the pressure of an unsolicited offer, the time for an Executive Briefing has probably passed. In that case, reach out to me directly at [email protected] with the subject line “Already in It.” No pitch. Just a conversation between two people who take this seriously.

The 95% who attempt this alone are not bad operators. They are good operators who didn’t know what they didn’t know. You now know. That changes what you do next.

… Ben

Author: Ben Griffin

Facilitator - CEO Peer Advisory Group; Executive Coach; Photographer