What makes a great business owner can make a poor seller

Scott Bushkie

Guest Columnist

December 15, 2025

After 25 years of working with founders and entrepreneurs, I’m still struck by one thing: The same traits that make someone brilliant at building a business can work against them when it’s time to sell it.

These are people who can take an idea from nothing, build it into a company that supports dozens, or hundreds, of families and navigate challenges most people would run from.

Yet when it comes to selling their businesses – their single largest financial asset – success rates are shockingly low.

Industry experts have been saying for decades that only 20-30% of companies successfully sell.

With all the information available today, you’d think that number would climb.

It hasn’t.

At Cornerstone, we wanted to understand why.

Not the surface-level reasons, but what’s actually happening inside the mind of a seller.

So, we hired a professional research firm to find out.

They interviewed 750 business owners, ages 45-75, with businesses generating $5 million to $100 million in revenue, across every region of the U.S.

We wanted to look directly at how owners think and the assumptions they make about selling their business.

Some findings confirmed what we suspected.

Others surprised us.

But together, they painted a clear picture of why so many sales fail, or close far below potential value.

Owners don’t know what their business is actually worth

One of the most striking research findings was that more than 60% of owners have never had any kind of valuation or market analysis done on their business.

And even more surprising: 55% said if an offer “felt reasonable,” they would take it without talking to anyone else.

That means most owners are fielding life-changing offers with no benchmark, no prep work and no competitive pressure.

On the surface, that seems illogical.

These are smart, capable people who run complex companies.

So, why would they approach the biggest financial transaction of their lives this way?

Now consider the traits that make entrepreneurs extraordinary builders: grit, optimism, self-reliance, a bias for action, the confidence that “I’ll figure it out” and a lifetime of solving problems through trial and error.

These are the same traits that push them to:

• Trust their instincts instead of getting a valuation
• Rely on personal judgment rather than external expertise
• Believe they can “handle” a sophisticated buyer on their own
• Treat selling a company like another challenge they can muscle through

These tendencies serve them beautifully when growing a business.

But in a sale, they become liabilities.

Buyers don’t rely on instinct – they rely on data, strategy, leverage and repetition.

They buy companies for a living.

Business owners sell one, maybe two companies in their lifetime.

That experience gap is massive.

And when an owner brings builder traits into a seller’s arena, they almost always walk in underprepared and undervalued.

This is why so many are vulnerable to the first buyer who shows up with praise, promises and a number that “seems about right.”

It’s not a lack of business savvy – it’s the misapplication of strengths.

And it’s exactly why so many great owners become poor sellers, often without realizing it until it’s too late.

Seller beware: You need a team

Business owners are some of the smartest, most capable people I’ve ever met.

But most owners only sell a business once.

Buyers do this every day.

If you don’t build the right team – a tax strategist, an M&A advisor, a specialist M&A attorney and a financial advisor – you face two risks:

• You may not sell at all.
• Or, if you do sell, you may leave millions, sometimes tens of millions, on the table.

Understanding your strengths also means knowing where you need help.

Because the skills that built your company are not the same skills required to sell it.

And when it comes time to exit, you deserve the outcome you’ve earned.