I used to be a pretty good pitcher.
Then one season I joined a new team. I showed up thinking I would be on the mound. The coach had other plans. His son was a pitcher, and from the first practice I was told in a hundred small ways that I was not good enough. Wrong mechanics. Wrong attitude. Wrong arm. I spent the season being measured against a standard that was never about me.
By August I could barely throw a strike. The arm had not changed. The pitcher had not changed. What changed was that I had let someone else decide what I was worth. Once I accepted his version of me, my body followed.
That was Little League. The stakes were a trophy and some orange slices. But the lesson has stayed with me through every chapter of my career, and I watched it play out again this month with a business owner I work with.
She was running an exceptional company. Strong margins. Growing revenue. A team that delivered. She walked into the sale process from a position of strength. She knew her numbers. She knew her market. She signed a letter of intent with a buyer she believed in, and we moved into due diligence.
Then the grinding began.
Four months of requests. Endless data rooms. Endless questions. Every conversation framed around what could go wrong. Every meeting focused on the weakness, the gap, the risk, the thing she could not perfectly explain. The buyer was doing his job. That is what buyers do.
But something happened inside her during those months. The owner who walked in confident began to talk about her business differently. The wins got smaller. The flaws got bigger. She stopped describing a company that was thriving and started describing a company with problems. The numbers had not changed. Her customers had not left. Her team was still delivering. What changed was that she had let the process define her.
And then the buyer backed out. Could not get financing. Five months gone. No deal.
That is when I saw it. The same look I felt in myself thirty years ago after a season of being told I was the wrong pitcher. She was questioning her own value. She was asking whether the business was actually worth what we had said it was worth. She was wondering whether the next buyer would find the same problems and walk for the same reasons.
This is one of the most dangerous moments in a sale, and almost no one warns sellers about it. Doubt is poison in a deal. Buyers can smell it. The next one will read it on your face in the first meeting. Once you start negotiating from a place of self-doubt, you negotiate against yourself before the other side ever has to.
So I told her what I wish someone had told that twelve-year-old kid on the mound. Your business is astonishing. Your numbers are real. Your customers are real. The fact that one buyer could not arrange financing is a fact about that buyer, not a fact about you. Do not let a process that was designed to find problems convince you that you are a problem.
In my latest book, The Business Sale Paradox, I write about the Shifting Power Dynamics of a sale. The process moves through phases. In The Courtship Phase, the buyer chases. They flatter. They tell you how special the business is. Then you sign the letter of intent and you enter The Reality Check. The buyer’s job changes. They are no longer selling you on the deal. They are now looking for every reason to lower the price or walk away. The questions get harder. The tone gets colder. If you are not prepared for this shift, you will internalize it.
Most owners are not prepared. They are not warned. They walk into due diligence still riding the energy of The Courtship Phase and they get whiplash. The owner who was being courted is now being interrogated, and it feels personal because for most owners the business is personal.
The work is to hold two truths at once. You have to take the buyer’s questions seriously enough to answer them well, and you have to refuse to let those questions rewrite your understanding of what you have built. The business that was great in month one is still great in month five. The questions are not a verdict on your company. They are a phase of the process.
When a deal falls through, and many do, the same discipline applies. The buyer’s inability to close says something about the buyer. It does not say something about you.
I have started calling this the Internal Rate of Resilience. Buyers obsess over IRR. Owners need to measure their own.
I learned this lesson too late to save that Little League season. I am still working on it as an adult. But I can tell you this. The day you let someone else decide what you are worth is the day you stop being able to throw strikes.
Do not give that power away. Not on the mound. Not at the negotiating table.
This content is for educational purposes only and does not constitute investment, legal, tax, or financial advice. Robert Pagliarini is a Wealth Advisor at Beacon Pointe Advisors, a Registered Investment Adviser. Portions of this content were drafted with the assistance of AI tools and reviewed for accuracy.