Why So Many Small Businesses Struggle to Sell

Every year, thousands of small business owners start asking the same question: What’s next?

For many, the answer should be simple: sell the business, pass it on, and let it continue to thrive. But in reality, most owners discover that selling a business is harder, slower, and more emotional than anyone prepares them for.

Across the U.S., nearly 2.9 million privately held businesses are owned by Baby Boomers. Together, those companies employ over 32 million people and generate $6.5 trillion in revenue. Within the next decade, about 60% of those owners plan to retire or sell.

Here’s the hard truth:

Only 20–30% of businesses that go to market actually sell.

The rest quietly close their doors. Not because they weren’t valuable, but because they weren’t ready.

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The unseen crisis of small business succession

Small businesses make up 99.9% of all U.S. companies and employ nearly half of the workforce. They are the backbone of local economies. The places we buy coffee, fix our cars, and build our first careers.

But right now, we’re facing what experts call a succession crisis.

Many owners wait too long to plan their exit. Their financials live in multiple spreadsheets. Their operations depend entirely on them. And their story, the “why” behind everything, rarely makes it into the numbers.

When a buyer comes in, what should be a clean handoff turns into confusion. Deals stall. Value erodes. And the legacy that took decades to build becomes vulnerable to a rushed decision.

In short:

• Only one in four listings ever sells.
• Most deals take six to nine months, but many never close.
• Unrealistic pricing, messy books, and owner dependence are the top reasons buyers walk away.

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The human cost behind the numbers

Behind every failed sale is a story. An owner who poured their life into something meaningful. Employees left wondering about their jobs. A community that loses a cornerstone.

When these transitions fail, the impact ripples far beyond balance sheets. It affects local economies, family wealth, and neighborhood stability.

At Rowan, we don’t see this as a marketplace problem. We see it as a human one.

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What Rowan does differently

Rowan exists to guide both sides: the seller who built it and the buyer who will carry it forward.

We combine human guidance with modern tools to make the handoff clear, dignified, and successful.

Our process helps owners:

• See the real story behind their numbers. We clean up and clarify financials so buyers can trust what they see.
• Understand what buyers value. We benchmark readiness and show where to strengthen operations before listing.
• Find the right successor. We match businesses with qualified, mission-aligned buyers who are ready to lead.
• Protect their legacy. We ensure employees, customers, and community relationships carry forward.
  
  

For buyers, we remove the guesswork. No hidden chaos. No surprises after closing. Just clarity to lead with confidence.

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The road ahead

The great handoff of American small businesses is already underway. Every successful transition means preserved jobs, thriving communities, and owners who get to see their life’s work continue.

Rowan’s mission is to make that possible. To turn what is often a confusing, stressful process into one defined by clarity, care, and confidence.

Your business deserves a future.

And you deserve to hand it off knowing it’s in good hands.

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Interested in buying or selling a business?

Learn more about how we can help you start your next chapter: hello@trustrowan.com