Why Business Owners Decide to Sell: Lessons from the 17% Club

After participating in more than 100 business transactions, I’ve learned that business owners rarely wake up one morning and decide, “Today’s the day I sell my business.”

The decision has usually been years in the making.

Sometimes it’s driven by opportunity. Sometimes by family. Sometimes by growth. And occasionally, it’s the result of an unsolicited offer that simply can’t be ignored.

As Founding Partner at NorthStar Mergers & Acquisitions, I’ve had the privilege of helping owners navigate that decision and ultimately transition their businesses on their terms.

In doing research for my book, Maximize Business Value, Begin with the Exit in Mind, I found that statistics show only about 17% of business owners successfully transition their businesses. I wanted owners to hear directly from those who had done it successfully—not just how the transaction worked, but why they decided it was time, what surprised them, and what they learned along the way.

While every story was different, I noticed something interesting.

The reasons they sold varied dramatically.

The lessons they left behind were remarkably consistent.

Here are four conversations that continue to stick with me, along with the amazing lessons.

Preparation Creates Opportunity

When I interviewed Randy Haran, one thing immediately stood out.

His successful sale actually began years before his business ever changed hands.

Several years earlier, another buyer had expressed interest. The transaction never happened, but

Randy described the experience as a “dress rehearsal.”

That failed deal turned out to be incredibly valuable.

He learned what buyers asked for.

He learned what due diligence really looked like.

He learned where the business was strong—and where it wasn’t.

So when the right buyer eventually appeared, Randy wasn’t trying to prepare under pressure. He had already lived through the process once.

Tom’s Take

This is something I wish every business owner understood.

Preparation isn’t something you do once you’ve decided to sell.

Preparation is something you do while you’re still building the business.

The owners who achieve the best outcomes don’t spend six frantic months getting ready for the market. They spend years building companies that are attractive, transferable, and well-documented.

That’s one reason unsolicited offers often surprise owners. Opportunity rarely gives you six months to prepare.

It shows up unexpectedly.

When it does, you’re either ready—or you’re not.

At NorthStar, we often remind owners that preparation doesn’t obligate you to sell.

It simply gives you the ability to decide from a position of strength rather than under pressure.

Selling Can Be the Best Growth Strategy

One of my favorite conversations was with Mitch Felderhoff.

His family business had created an entirely new product category.

Demand wasn’t the problem.

Growth was.

The business needed facilities, equipment, and capital that simply couldn’t be funded through retained earnings anymore.

Instead of slowing down, Mitch and his family chose to bring in a strategic partner who could help the business reach its next stage.

They weren’t walking away from the company.

They were investing in its future.

Tom’s Take

Many business owners assume selling means retirement.

I’ve found that’s rarely true. Look at me.

Some of the strongest transactions I’ve been involved with happened because owners wanted more for the business than they could accomplish on their own.

The right buyer may bring:

• Capital to accelerate growth

• New markets and distribution channels

• Operational expertise

• Technology and infrastructure

• Leadership depth

• Strategic acquisitions

In other words, selling isn’t always the finish line.

Sometimes it’s the catalyst for the next phase of growth.

That’s why choosing the right buyer matters just as much as negotiating the right price.

Buyers Don’t Find Businesses for Sale. They Find Businesses Worth Buying.

Tom Washington shared a story that many owners dream about.

He wasn’t actively marketing his company.

Instead, buyers kept approaching him.

Eventually, one presented an all-cash offer, minimal due diligence, and a remarkably fast closing timeline.

Owners often hear stories like that and think, “I wish someone would call me.”

But that’s not the real lesson.

Tom’s Take

Exceptional offers rarely happen because a business is for sale.

They happen because a business is exceptionally attractive.

When strategic buyers look at acquisition opportunities, they’re asking one fundamental question:

Can this business continue to succeed without the current owner?

The businesses that command premium valuations typically share similar characteristics.

Their financial statements are clean.

Revenue is predictable.

Customers are diversified.

Processes are documented.

Leadership extends beyond the founder.

The owner isn’t involved in every decision.

Those aren’t simply buyer preferences. They’re characteristics of a healthy business.

Ironically, owners who build companies this way often create businesses they enjoy owning even if they never decide to sell.

Sometimes the Business Isn’t What Changes

Perhaps the most personal conversation was with John Humphrey.

His company remained successful.

The financials weren’t the issue.

The business simply evolved into something different than what energized him.

John described himself as “a builder, not a maintenance guy.”

That statement has stayed with me.

Entrepreneurs are builders by nature.

At some point, many companies mature beyond constant innovation and enter a phase focused on optimization, systems, and scale.

For some founders, that’s exciting.

For others, it’s time for a new challenge.

Tom’s Take

One misconception about selling is that every decision is financially driven.

In reality, life has a tremendous influence on transition decisions.

I’ve worked with owners who sold because of:

• Health concerns

• Family priorities

• Partner disagreements

• Succession challenges

• Burnout

• Estate planning

• New opportunities

Those reasons aren’t weaknesses.

They’re realities.

The mistake is waiting until one of those realities forces your hand.

Transition planning isn’t about deciding to sell.

It’s about making sure life doesn’t make the decision for you.

The Lesson Every Business Owner Should Remember

When I look back at these conversations, I don’t see four owners who sold businesses.

I see four owners who built businesses that gave them choices.

• One chose to capitalize on years of preparation.

• One chose growth.

• One responded to an extraordinary opportunity.

• One recognized it was time for his next chapter.

Different reasons.

Different industries.

Different businesses.

The common denominator wasn’t why they sold. It was how prepared they were when the opportunity arrived. That’s the lesson I hope every business owner takes away from this article.

At NorthStar Mergers & Acquisitions, we don’t believe every business owner should sell today.

In fact, sometimes our advice is to wait.

Our responsibility is to help owners understand what buyers value, identify opportunities, evaluate their options, and navigate the transaction when the timing is right.

Because the best exits don’t begin with a Letter of Intent.

They begin years earlier, when an owner intentionally builds a business that is valuable, transferable, and ready for whatever comes next.

The owners in the 17% Club didn’t all follow the same path.

But they all reached a place where they could make one of the most important decisions of their lives on their own terms.

That’s what every business owner should be working toward.

About the Tales from the 17% Club

The Tales from the 17% Club was a special podcast series I hosted on the Maximize Business Value Podcast, featuring candid conversations with business owners who successfully transitioned their companies. Their stories reinforce something I believe deeply: business owners learn best from other business owners.

Each conversation offers practical insights into the decisions, challenges, and lessons that shaped a successful transition. If you’re building your business with the future in mind—even if a sale is years away—I encourage you to explore the series. My hope is that their experiences will help more owners prepare earlier, make more informed decisions, and ultimately become part of the 17% who successfully transition their businesses on their own terms.

Want to hear these stories firsthand?

Watch the full 17% Club interviews with Randy Haran, Mitch Felderhoff, Tom Washington, and John Humphrey to hear their lessons and prepare for your own successful exit.

Listen to the full conversation with Randy Haran, Tales From the 17% Club, on the Maximize Business Value Podcast.

Listen to the full conversation with Mitch Felderhoff, Tales From the 17% Club, on the Maximize Business Value Podcast.

Listen to the full conversation with Tom Washington, Tales From the 17% Club, on the Maximize Business Value Podcast.

Listen to the full conversation with John Humphrey, Tales From the 17% Club, on the Maximize Business Value Podcast.

About NorthStar Mergers & Acquisitions

Based in Dallas, Texas, NorthStar Mergers & Acquisitions guides business owners through one of the most significant financial and emotional journeys of their lives—the sale of a company. Specializing in lower middle-market transactions across multiple industries, NorthStar combines deep valuation expertise, strategic marketing, and buyer engagement to ensure every client achieves their dream exit.

Visit NorthStar-Mergers.com to learn more about how NorthStar helps business owners navigate their ideal transition.