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
Due Diligence
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
Due Diligence Is About What Can Walk
Assets depreciate.Contracts expire.People walk. If due diligence doesn’t focus on what can leave the day after closing, it’s incomplete — regardless of price paid. The real risk is what walks away.
Experience Asks Hard Questions Early
Seasoned acquirers ask uncomfortable questions before money changes hands. Inexperience postpones them — and pays for it later. Experience matters most in due diligence. Hard questions are cheaper early.
Strong-Arming Is Not Integration
Pressure is not integration strategy. Integration works when people feel respected, informed, and aligned — not coerced. Experienced acquirers build trust before authority. Integration follows trust.
Deals Fail Quietly First
Most deals don’t fail at closing. They fail months later — when talent leaves, knowledge disappears, and continuity breaks. By then, the check has cleared. Early due diligence prevents late regret.
Retirement Risk Must Be Modeled
When an owner plans to retire shortly after closing, due diligence must answer one question: “Who actually runs the business next?” If that answer isn’t clear, the deal isn’t ready. Succession risk is deal risk.
Key Employees Are Not Replaceable on Day One
Some roles take years to replicate — if they can be replicated at all. Assuming immediate replaceability is not strategy.It’s denial. Experienced buyers identify single-point-of-failure roles early. Replaceability is often overstated.
Highland Global Business Valuations 