When a valuation comes in below price, you learn a lot by what happens next. A disciplined group says:“Okay. What does this tell us about pricing and risk?” A motivated group says:“Okay. How do we get this to support the price?” Once the valuation gap is treated as a “problem to solve,” it stops being … Continue reading The Valuation Gap Becomes a “Problem to Solve,” Not a Signal to Respect
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.
Moral Hazard in Deals Isn’t Evil. It’s Incentives
“Moral hazard” sounds dramatic, but most of the time it’s not malicious. It’s a simple reality: When the people making decisions don’t bear the full cost of the downside, the decision-making changes. If a broker gets paid at closing, their economic incentive is the closing.If a seller exits at closing, their risk ends at closing.If … Continue reading Moral Hazard in Deals Isn’t Evil. It’s Incentives
When Everyone Wins at Closing, Someone Usually Loses Later
Some deals close with universal smiles. Buyer gets the keys. Seller gets paid. Broker gets the fee. Lender gets the loan booked. And the problem is… that is not the same thing as a good deal. Because a closing can be engineered even when the economics are weak. You can negotiate terms, stretch assumptions, layer … Continue reading When Everyone Wins at Closing, Someone Usually Loses Later
The Moment You Need the Valuation to Work, the Deal Has a Risk Problem
Let me say it plainly: The moment a buyer needs the valuation to support the purchase price, the deal has shifted from analysis to attachment. And attachment is where risk hides. A valuation isn’t a hurdle.It’s a signal. If the business is worth less than the price, the conclusion isn’t “fix the valuation.” The conclusion … Continue reading The Moment You Need the Valuation to Work, the Deal Has a Risk Problem
Walking Away Is a Skill
Walking away is not failure. Sometimes it’s the most profitable decision you’ll ever make. Because the deals you avoid don’t show up on your balance sheet—but they absolutely shape your financial life. Buyers often think the goal is ownership. The real goal is ownership of the right business at the right price with the right … Continue reading Walking Away Is a Skill
Risk Mitigation Isn’t “Getting Comfortable.” It’s Getting Specific.
I hear a lot of vague risk language: “I feel good about it.”“We’re comfortable.”“It’ll work out.” Real mitigation is specific: What risk? What plan? What cost? What timeline? What contingency? When buyers are emotionally invested, specificity disappears. Because specificity invites hard questions. Discipline invites them anyway.
The Best Deals Survive Scrutiny
A strong deal doesn’t need the valuation “fixed.” A strong deal might need adjustments, explanations, reconciliation—sure. But it doesn’t require contortions. It survives scrutiny because the economics support it. That’s the quiet difference between deals that become assets and deals that become burdens. If scrutiny breaks the deal, the deal wasn’t strong.Scrutiny just revealed it.
Overpaying Doesn’t Always Look Like a Problem at Closing
Here’s why overpaying is so dangerous: It often doesn’t look like a disaster at closing. The first few months can feel great. New energy, new focus, adrenaline. But the price premium shows up later: in thin coverage, in delayed reinvestment, in stress during slow seasons, in inability to absorb shocks. Valuation gaps don’t disappear. They … Continue reading Overpaying Doesn’t Always Look Like a Problem at Closing
Leadership Sometimes Means Disappointing People
If your job is risk management—whether you’re a buyer, lender, or advisor—there will be moments when someone is unhappy with you. That’s the job. If your risk decisions are always popular, you’re probably not making risk decisions. You’re making customer service decisions. There’s nothing wrong with service. But leadership is the willingness to protect people … Continue reading Leadership Sometimes Means Disappointing People
“Everyone Agrees” Isn’t a Credit Factor
Some deals get momentum because “everyone’s aligned.” Buyer, broker, seller, lender, advisors—everyone wants it done. But alignment is not the same as safety. In fact, alignment can be dangerous when it’s driven by shared incentives instead of shared realism. One of the most underrated leadership skills in lending is the ability to be the adult … Continue reading “Everyone Agrees” Isn’t a Credit Factor
Highland Global Business Valuations 