Avoiding the 75%: Why So Many Owners Regret Selling Their Business

Businessman in suit standing at a crossroads, avoiding the 75%If you’re planning to sell your business someday, here’s a statistic worth sitting with: research from the Exit Planning Institute and PwC found that 75% of business owners feel “unhappy” or “profoundly unhappy” one year after exiting their company. Three out of four owners who worked hard to build something, then sold it or handed it off end up regretting how it turned out.

That’s not a small problem. And it’s been true for over a decade, which tells you something: most exit planning still focuses almost entirely on the transaction, not on what happens to you after the deal closes.

The real issue isn’t the money; it’s the identity loss

If you’ve run a business for any length of time, your company isn’t just an asset. It’s woven into who you are. Your family may see you as the success story. Your friends, many of whom are probably your employees, envy that you don’t answer to a boss. Your community expects you (and your company) to show up and give more, because you’re “the owner.”

Your business shapes your daily interactions, your standing among peers, and your sense of purpose. So when you sell or step away, it’s not simply a financial transition; it’s a personal one. Being introduced as a “former owner” or lumped in as “retired” can feel like erasure, not freedom. That disorientation is a huge part of why so many owners end up unhappy, even when the deal itself went well financially.

Most owners don’t plan for what comes next

Business owners are goal driven. You’ve spent years chasing targets and clearing the next hurdle. Yet when it comes to planning life after your business, most owners are flying blind: only 17% have a written plan, and nearly half have no plan at all.

Think about what that transition actually demands. You’re not just changing your income source, you’re losing:
• The steady stream of small wins that come from daily decision-making
• 40, 50, or 60 hours a week that used to be filled with purpose
• The satisfaction of building strategy, developing people, and steering a team

If nothing replaces that, boredom, restlessness, and regret tend to fill the gap — regardless of how large the check was.

What a good exit actually requires

A successful exit isn’t just about maximizing sale price. It’s about walking into something you’re genuinely excited about — not just walking away from something familiar. That means thinking through, well before you sign anything:

• What does a fulfilling week look like without the business?
• What replaces the sense of purpose and decision-making you’re used to?
• Are your expectations about timing, value, and readiness realistic?

Selling your business will likely be the largest financial event of your life. But it’s also one of the most significant identity shifts you’ll ever go through. The owners who avoid the 75% are the ones who plan for both.

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What’s Your Business Really Worth? (Probably Not What You Think)

If someone asked you right now what your business is worth, you’d probably answer fast, and with total confidence. That number’s likely made its way into conversations with your banker, onto a personal financial statement, maybe even into a retirement plan your financial advisor put together.

Here’s the uncomfortable part: there’s a good chance that number is off by 50% or more.

That’s not a knock on you. It’s just that most owners have never had access to the information needed to value their business accurately. If your retirement plan is built on a made-up number, the whole plan is distorted.

Your Business Might Be Most of Your Net Worth

For many owners, the business isn’t just a major asset, perhaps 70% or 80% of everything they’ve built. Yet very few owners have ever had that number evaluated with a professional appraisal. Most are working off a guess, and after enough time, that guess starts to feel like fact.

Where That Number Usually Comes From (And Why It’s Wrong)

Ask most owners how they landed on their valuation, and you’ll hear one of three stories:

    1. Someone at a conference sold a business “kind of like mine.” That’s hearsay, not data.

    2. A public company in the industry got acquired, so they applied that multiple to their own revenue. Public company deals include a premium for liquidity and scale that a small private business doesn’t get.

    3. They worked backward from what they needed to retire comfortably. That tells you what you want, not what a buyer will actually pay.

None of these is a real valuation. But once the number gets repeated to a banker or advisor a few times without pushback, it hardens into “fact” and it gets harder to question the longer you believe it.

What Buyers Are Actually Paying

If your business sells for under $2 million, your buyer is most likely an individual who plans to run it themselves and pay off the purchase with the business’s own cash flow. They’re pricing you off Seller’s Discretionary Earnings (SDE), your total financial benefit as owner, including salary, benefits, perks, and profit.

The going rate: 2 to 3 times SDE. Push much past 2.5x, and the math stops working for the buyer. They can’t service the debt and still pay themselves enough to make it worth it.

Bigger companies attract a different buyer entirely, private equity or strategic acquirers, who pay 4 to 7 times EBITDA. Different buyer pool, different financing, different expectations for what the business needs to look like.

Mixing these up by pricing off revenue instead of earnings or applying EBITDA multiples when you should be using SDE, anchoring to a number a competitor mentioned sets an expectation no real buyer will meet. That’s how deals fall apart, and how businesses sit unsold for years.

The Fix Is Simple: Get a Real Number

If your business is a major piece of your net worth, as it is for most owners, start your planning with a qualified business appraisal. Not a broker’s ballpark estimate pitched to win a listing. Not a multiple you saw in a trade article. An actual appraisal from a credentialed valuation professional who looks at your financials, your industry, your market, and your specific risk factors.

This appraisal will cost a few thousand dollars. For the asset that likely represents the bulk of your net worth, that’s a rounding error, and it’s the one number every other decision about your retirement, your exit, and your future should be built on.

Until you have it, every projection you’re working with is a best guess dressed up to look official.

Posted in Building Value, Entrepreneurship, Exit Planning, Exit Strategies | Tagged , , , , , | 1 Comment

One Response to What’s Your Business Really Worth? (Probably Not What You Think)

  1. David J Sweeten says:

    Very true. Some banks like say Celtic Bank (John Park) will take the financial information(Tax Returns and financial statements) needed for a reasonably accurate value and what they will lend on the sale of the business. Accrual basis is most important as banks lend on cash flow and accrual based is the only real acceptable accounting method as opposed to the cash basis which is not GAAP and is how so many companies file their tax returns-Cash basis!

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Layers of Disclosure:
A Business Owner’s Guide to Sharing Information in a Sale

If you’re selling a privately held business, disclosure is rarely just a matter of completing a checklist. It’s more like managing a series of “layers” that unfold over time. The timing, depth, and framing of what you share can affect how buyers value your company, how much leverage you retain at the negotiating table, and often overlooked how stable your business remains while the transaction is moving forward.

A practical way to think about disclosure is this: you should expand what you share only as the buyer becomes more committed, receives greater legal protections, and the deal becomes more certain. In other words, disclosure should be tied to deal momentum, not simply to the passage of time.
Layers of Disclosure. Geometric design with layers of translucent squares.
In the earliest stage of a sale, the goal is to generate interest without creating avoidable exposure. Buyers often start with something like a blind offering flyer or teaser, enough information to understand the general nature of the business and its potential, but not enough to identify you, your customers, or your ownership details. Typically, this means the information stays high-level: the industry, a general description of the business model, an approximate revenue range, and a broad growth narrative.

Once a prospective buyer signs a nondisclosure agreement, the disclosure layer increases. This is where you move toward a Confidential Information Memorandum (CIM), which is designed to give the buyer real context about how the business works: how it makes money, where it competes, and what the financial performance looks like over time. At this point, financial statements and a clearer explanation of management’s view of the business are appropriate. However, it still doesn’t mean everything needs to be fully transparent. Even here, it’s common to summarize sensitive information rather than release it in full. Customer names may be withheld or represented in a summarized form, employee compensation may not be provided at an individual level, and proprietary pricing or particularly sensitive contract terms are often handled carefully.

As discussions progress and you move toward a Letter of Intent (LOI), buyers typically need enough detail to understand risk and value with greater confidence. But it’s still not the moment to hand over every underlying document that would allow them to “reverse engineer” the business if negotiations fail. This stage is usually about explaining value drivers including working capital realities, capital expenditure needs, and known risks—without immediately providing complete documentation to support every assertion.

Once an LOI is accepted, the process shifts from exploration to verification and execution. At that point, deeper disclosure becomes more reasonable because the buyer is showing real commitment and the deal terms are becoming defined. After the LOI, controlled release of items like customer lists, more granular financial schedules, key contracts, and additional organizational information becomes more common. Even then, sequencing still matters. Some details, especially those that could create unnecessary disruption, such as certain compensation information or sensitive customer relationships, may still be phased in gradually.

During formal due diligence, disclosure becomes comprehensive and evidentiary. This is when items like tax filings, regulatory matters, customer agreements, intellectual property documentation, and detailed operational information are appropriate. The aim is to be complete while also avoiding unnecessary disruption to employees, customers, and vendors. A sale process can already be distracting, and you don’t want disclosure practices to add chaos on top of it.

Finally, some disclosures are best held until closing is genuinely close. Certain actions, like notifying customers and employees, seeking change-of-control consents, granting banking access, or sharing operational credentials can create instability if the transaction falls through. Holding these items back protects the business while the outcome is still uncertain.

Throughout the process, the role of an advisor is to help you treat disclosure as a structured pacing decision rather than a one-time event. When disclosure is handled correctly, you reduce execution risk, protect your leverage, and increase the odds that an LOI becomes a real closing, not a costly false start.

If you’d like, share what stage you’re in (early conversations, CIM stage, LOI discussions, or due diligence) and what type of business you run. I can outline what disclosure typically should look like at that specific point—along with what’s usually better to delay.

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Exit Planning: If Not Now, When?


You’ve probably said it yourself: “Talk to me in five years.”

It’s the most common response advisors hear — and it makes sense. You’re heads-down building, not winding down. Exit planning feels like a conversation for later. The business is performing. You have time. And honestly, it’s a lot to think about.

But here’s the uncomfortable truth: later is exactly when most exits go wrong.

You’re already doing exit planning — just not deliberately

Think about the early-stage tech founder. Obsessed with product, grinding 80-hour weeks, convinced the exit is the last thing they should be thinking about. Yet their investors demand an exit strategy on day one — not because they plan to push the founder out, but because articulating the end game forces clarity on everything else.

How does the business scale beyond you personally? What leadership structure does a bigger organization need? What changes in operations and governance will sustain growth? Which decisions build value, and how will that value eventually be realized?

These aren’t exit questions. They’re the right business questions — and exit planning forces you to ask them.

As a privately held owner, no investor is requiring this of you. That’s both a freedom and a vulnerability. Your emotional investment in the business is real. But the business itself has no such attachment. If it succeeds, it needs to run without depending entirely on you. In fact, the more successful it becomes, the less it can afford to.

“I’m focused on building the business,” but building toward what?

Once your personal financial security is solid, continued growth primarily serves the business, not you. That’s fine — but it’s worth naming. Businesses don’t fail because they reach maturity. They fail because transitions are mismanaged.

Exit planning isn’t just a pricing conversation. What your business is worth matters, of course. But equally important — and often ignored — is whether you are ready for life after the business, and whether your organization is ready for new leadership and ownership.

Miss either of those, and even a strong headline valuation won’t save the outcome.

A real exit plan works on three things at once:

  1. Enterprise value: what drives it, and how to grow it
  2. Owner readiness: your financial and personal preparation for what comes next
  3. Organizational readiness: the people, systems, and structure that make the business transferable

It’s a serious undertaking. Which is exactly why the right time to start isn’t in five years.

It’s now.

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What to Watch Out for When Getting Outside Advice

When you bring in an outside advisor — whether it’s an accountant, attorney, consultant, or broker — you’re doing the right thing. You’re acknowledging there’s something you don’t know and going to find someone who does. That’s smart ownership.

But there’s a trap hidden in that process that most business owners never see coming.

Every Expert Has a Favorite Tool

There’s an old saying: to a hammer, everything is a nail.

Think about it this way. You go to your doctor and say, “My shoulder has been killing me — I need help.” The doctor genuinely wants to help you. But whether you walk out with a prescription, a surgery date, a chiropractic adjustment, or a set of acupuncture needles depends less on what’s actually best for your shoulder — and more on which type of doctor you happened to walk in to see.

The internist reaches for anti-inflammatories. The orthopedic surgeon schedules an operation. Each one treats your pain. Each one probably helps. But you’ll likely never realize that your treatment was shaped by who you chose to see, not by some universal best practice for shoulder injuries.

The same thing happens when business owners seek outside help.

The Advisor You Hire Shapes the Advice You Get

When it comes to something as significant as planning your exit from a business, the type of advisor you engage will heavily influence the direction you’re pointed — often without you realizing it.

Bring in an accountant and the plan will likely center on minimizing your tax burden. Hire an attorney and you’ll probably end up focused on asset protection or employment contracts. Work with a business consultant and the conversation will revolve around improving operations and boosting profitability.

None of that advice is wrong. But it may not be complete — and it may not actually align with what you’re trying to accomplish in your life.

A few years ago, a business broker added “Exit Planner” to his business card. When asked how he approached exit planning, his answer was straightforward: if an owner would agree to accept 100% seller financing, he’d help them sell. That was his tool, and he applied it to every situation.

To a hammer, everything is a nail.

What This Means for You

Before you take any advisor’s recommendation and run with it, it’s worth asking yourself: Is this the best solution for my situation — or is it the best solution this particular advisor knows how to deliver?

That’s not cynicism. Most advisors genuinely want to help. But their training, their experience, and frankly their business model all point them toward certain kinds of answers.

The best advisors — the ones worth your time and money — will ask a lot of questions before they start offering solutions. They’ll slow down, make sure they understand your real objectives, and resist the urge to jump straight to their preferred tool.

If an advisor walks into your first meeting already knowing what you need, that’s worth paying attention to. The clarity that comes from being genuinely heard saves time, prevents costly missteps, and leads to a plan you’ll actually follow through on.

The right advice starts with the right questions — not the other way around.

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