Some purchase price conflicts are technical. But many are emotional. When a buyer suddenly becomes interested in enterprise vs. equity distinctions only after a valuation comes in low… that’s not curiosity. That’s a pressure response. The buyer is trying to find a “math door” that leads back to the number they already chose. And lenders … Continue reading Enterprise Value vs. Equity Value Confusion Isn’t Always a Mistake
Experience Matters Most: Where Judgement Meets Reality
Experience Matters Most is a collection of observations drawn from years of watching decisions play out beyond the spreadsheet. These posts explore leadership, risk, valuation, and integration through the lens of real-world outcomes—where assumptions are tested, pressure reveals priorities, and judgment determines whether value is preserved or destroyed.
This series focuses on the space between models and reality and is grounded in the belief that judgement is where theory meets consequence. They look beyond price and process to examine what actually drives continuity, erodes goodwill, and determines whether value endures after the ink dries. Because the most important risks—and the most important decisions—rarely appear in the model.
The Most Dangerous Sentence in a Deal
One of the most dangerous sentences I hear: “We’ll just grow into the price.” Sometimes businesses do grow. But when that sentence is used to justify a valuation gap, it’s often code for: “We’re comfortable paying for earnings that don’t exist yet.” That is a gamble—not a valuation. Calculated risk is fine. Unpriced risk is … Continue reading The Most Dangerous Sentence in a Deal
The Valuation Doesn’t Kill Deals. Weak Economics Do.
I’ve heard people say: “That valuation killed the deal.” Usually, that’s not accurate. The valuation didn’t kill it. The business’s ability to support the price killed it. The valuation just said it out loud. And in lending contexts, that distinction matters. Because you don’t want a deal that only survives if everyone agrees to ignore … Continue reading The Valuation Doesn’t Kill Deals. Weak Economics Do.
The “Just Add Back” Mentality
When buyers need the valuation to hit the number, you start seeing a specific kind of thinking: “Let’s add back this.”“And this.”“And this too.” Some addbacks are legitimate. But the behavior I’m talking about is different. It’s not normalization—it’s engineering. It’s the belief that if you adjust enough things, the business will become worth more. … Continue reading The “Just Add Back” Mentality
Arguing Methodology Instead of Economics
A common pattern when valuations come in low: Buyers don’t challenge the economic reality.They challenge the methodology. They argue multiple selection, capitalization rates, discount rates, adjustments, weightings, comps, assumptions. Sometimes those are fair discussions. But many times, the buyer’s real complaint is simpler: “This result doesn’t match what I want.” If the business truly supports … Continue reading Arguing Methodology Instead of Economics
The Valuation Isn’t There to Bless the Deal
A valuation isn’t a rubber stamp. It isn’t supposed to “make the deal work.” It’s supposed to answer one question: What is the business worth, based on the economics it has demonstrated? When a valuation comes in below the purchase price, the most revealing thing is the first reaction. Some buyers say:“Okay. What does this … Continue reading The Valuation Isn’t There to Bless the Deal
When Buyers Fall in Love With the “Before/After” Story
Some deals don’t get done because they’re bad businesses. They get done because the buyer loves the story. The turnaround story. The rescue story. The “I’ll take it to the next level” story. Stories are powerful. They’re also dangerous. Because stories can turn a valuation into an obstacle instead of a signal. And when a … Continue reading When Buyers Fall in Love With the “Before/After” Story
The Illusion of Control
First-time buyers often believe they can “outwork” risk. They think: “I’ll improve operations.” “I’ll grow sales.” “I’ll modernize marketing.” “I’ll hire better people.” “I’ll fix what the seller didn’t.” Maybe they will. But that’s not the point. The point is this: A plan to improve performance is not the same as proof of historic performance. … Continue reading The Illusion of Control
Confirmation Bias in a Suit
Most due diligence problems don’t happen because people skip due diligence. They happen because the due diligence becomes confirmatory. Everyone is busy. Everyone is professional. Everyone has checklists. But the questions shift from: “What could hurt us here?” to: “How do we justify moving forward?” When that happens, data stops being evidence and becomes a … Continue reading Confirmation Bias in a Suit
Sunk Costs Create Bad Math
Here’s something buyers rarely admit: They start counting money they already spent as a reason to spend more. Legal fees, deposits, inspections, travel, diligence consultants, time off work, negotiation fatigue… And then they treat those as “investments that must be recovered,” rather than what they actually are: Sunk costs. A valuation comes in light, and … Continue reading Sunk Costs Create Bad Math
Highland Global Business Valuations 