By the time an owner is ready to sell, most of the price has already been decided. The hardest conversation in this profession is not telling an owner their business is worth less than they hoped. It is explaining that the decisions which produced that number were made years ago, and that the window to … Continue reading Exit Readiness Starts Years Before the Exit
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.
What Buyers Actually Discount
Owner dependence is not the same problem as unverifiable risk — and only one of them is costing you money. Every owner of a small business has heard some version of the same warning: your company is worth less because it depends on you. That warning is half right. The half that is wrong costs … Continue reading What Buyers Actually Discount
A Valuation Is Not a Tool to Rescue a Bad Deal
There is a hard truth in transaction work that some people never fully accept: A valuation is not a tool designed to rescue a deal that does not work. It is not there to preserve momentum. It is not there to protect expectations. And it is certainly not there to manufacture support for a price … Continue reading A Valuation Is Not a Tool to Rescue a Bad Deal
Negative Free Cash Flow Is Not a Rounding Error
One of the most important inflection points in a valuation engagement occurs the moment adjusted free cash flow turns negative. That is not a minor inconvenience. That is not something to be explained away with enthusiasm, optimism, or deal fatigue. That is a serious analytical event. Too often, people look at reported earnings and assume … Continue reading Negative Free Cash Flow Is Not a Rounding Error
Asset-Heavy Businesses Still Require Credible Asset Evidence
One of the most common mistakes in lower middle market and SBA transactions is the assumption that “asset-heavy” automatically means “well supported.” It does not. A business may have substantial fixed assets. It may have meaningful inventory. It may present a balance sheet that appears to offer a backstop to the transaction. But appearance is … Continue reading Asset-Heavy Businesses Still Require Credible Asset Evidence
The Cheapest Path Is Often the Most Expensive One
There is a pattern I have seen many times over the years. A transaction has a valuation problem. The obvious solution is to obtain better evidence. An equipment appraisal is needed. An inventory review is needed. Some additional diligence is necessary to determine whether the value can actually be supported. And then someone says: “We … Continue reading The Cheapest Path Is Often the Most Expensive One
Early Bad News Is a Professional Courtesy
One of the most valuable things a valuation professional can say to a client is this: “Based on the information provided so far, this purchase price is unlikely to be supported.” Many people do not want to hear that sentence. They should. Because that sentence, delivered early enough, saves time, money, and false confidence. In … Continue reading Early Bad News Is a Professional Courtesy
Boundaries Are Part of the Value
One of the things that separates seasoned professionals from undisciplined ones is not just the quality of their analysis. It is the quality of their boundaries. In advisory work, boundaries are not administrative details. They are part of the value. They protect the integrity of the process. They protect the professional relationship. They protect the … Continue reading Boundaries Are Part of the Value
The Moment Clients Start Negotiating with the Math
There is a moment in some valuation assignments when the tone shifts. The client stops asking questions designed to understand the analysis. And begins asking questions designed to escape it. That distinction matters. A serious client wants clarity. A pressured client often wants a workaround. Once that shift occurs, the engagement becomes more delicate. Because … Continue reading The Moment Clients Start Negotiating with the Math
Sometimes the Most Valuable Answer Is “We Are Not the Right Firm for This File”
Not every assignment should be won. That is a lesson some firms learn late, and expensively. There is a temptation in professional services to chase the engagement, explain around the risks, and hope the file becomes workable once the formal process begins. Sometimes that happens. Often it does not. The more seasoned approach is different. … Continue reading Sometimes the Most Valuable Answer Is “We Are Not the Right Firm for This File”