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

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.

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.

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

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

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

Everyone focuses on closing. But the most important risk decision is earlier: Do the economics support the price? If not, everything else is downstream compromise. Structure can’t fix bad economics.Paperwork can’t fix thin margins.Optimism can’t fix insufficient cash flow. The discipline to slow down early prevents chaos later.

Lenders are human. They want borrowers to succeed.They want relationships.They want deals to close. But when a borrower is emotionally invested, that pressure transfers. It becomes subtle: urgency, exceptions, “just this once.” And over time, exceptions become habits. The best lenders I know don’t confuse customer service with risk blindness. They know the difference between … Continue reading Lenders Feel the Pressure Too

One of the most powerful questions in any acquisition: “If the numbers don’t support this… can you walk away?” If the answer is no, the buyer is no longer in control. And once the buyer isn’t in control, due diligence becomes compromised, negotiation becomes compromised, and the post-close plan becomes a fantasy. Because the buyer … Continue reading The Deal You Can’t Walk Away From Owns You

I hear this a lot: “It’s a simple business.” Maybe the operations are simple. But the economics are often not. Simple businesses can have complex risks: customer concentration, supplier dependence, labor volatility, margin fragility, regulatory exposure, key-person risk. When buyers say “simple,” sometimes what they mean is “I’m comfortable.” Comfort is not a risk metric.