In transactions, leadership, and lending, the most expensive lessons are often the ones people assume they won’t have to pay for. They assume goodwill will transfer.They assume people will stay.They assume leadership intent will overcome execution gaps. When those assumptions fail, the lesson is bought — sometimes at a very high price. What matters isn’t … Continue reading Bought Lessons and the Price of Value
Deal Attachment
Why Experience Changes Judgment
There’s a reason experience shows up as judgment rather than confidence. The best lessons are bought lessons — and they usually cost more than we expect at the time. They cost money, time, trust, or opportunity. Sometimes they cost all four. But what you get in return is perspective. People who haven’t paid for a … Continue reading Why Experience Changes Judgment
Bought Lessons Don’t Make You Bitter
“The best lesson is a bought lesson.” Some lessons don’t really land until they cost you something. Advice is helpful. Observation matters. But experience paid for with real consequences has a way of settling in permanently. In business and leadership, this shows up everywhere. The lesson you learn before a mistake is intellectual.The lesson you … Continue reading Bought Lessons Don’t Make You Bitter
The Best Lesson Is a Bought Lesson
My grandmother was born in 1913 and grew up on a farm during the Depression. They didn’t have much — but they had enough. Enough food, enough work, enough responsibility to understand that effort mattered and consequences were real. She knew hard work early. Farm work wasn’t optional, and nothing came easily. She earned a … Continue reading The Best Lesson Is a Bought Lesson
Value Doesn’t Disappear Overnight
Over the past weeks, I’ve written a number of posts about leadership, risk management, due diligence, integration, and goodwill. Individually, these topics are often discussed in isolation. In practice, they are tightly connected. Leadership behavior determines how risk is identified or ignored.Risk discipline determines how diligence is performed.Diligence determines whether assumptions about people, continuity, and … Continue reading Value Doesn’t Disappear Overnight
It All Made Sense…On Paper
In SBA business acquisitions, I see the same issue surface again and again: deals that make sense on paper but unravel after closing. In many cases, the valuation wasn’t “wrong.” The assumptions embedded within it — particularly around people, continuity, and leadership — simply weren’t tested or protected. SBA valuations require more than financial normalization. … Continue reading It All Made Sense…On Paper
Value Erosion Is Rarely the Math
After working on thousands of SBA-related business valuations, certain patterns become hard to ignore. When post-close issues arise, the problem is rarely the math. It’s usually leadership behavior, untested assumptions, or overlooked human capital risk that eventually surfaces as value erosion. My recent posts have sought to connect those dots — leadership, risk, diligence, integration, … Continue reading Value Erosion Is Rarely the Math
When Value Doesn’t Transfer
Goodwill is often treated as something that transfers at closing. In practice, it only survives if the conditions that created it remain intact. Leadership behavior, human capital decisions, and due diligence failures connect directly to goodwill erosion and value destruction.
The Valuation Isn’t the Problem
I’ve shared a series of posts on leadership, risk, diligence, integration, and goodwill. They aren’t separate ideas. They’re stages of the same story. Leadership behavior sets the tone.That tone determines whether risk is addressed or rationalized.Risk discipline shapes diligence.Diligence shapes assumptions about people and continuity.Integration reveals whether those assumptions were earned or merely convenient. And … Continue reading The Valuation Isn’t the Problem
Highland Global Business Valuations 