Your Business Is Probably Not Worth What You Think

Christopher Bowlby - Apr 03, 2026

Most private business owners have a number in mind. The problem is that it is often based on optimism, outdated comps, or someone else’s deal, not current market reality.

 

A lot of private business owners have a valuation in mind. Some arrived at it carefully. Most did not.

The most dangerous number in exit planning is often the one the owner feels most confident about. That number usually comes from a deal they heard about three years ago, a friend in a different industry, or a banker’s early ballpark from peak-market optimism.

A number repeated often enough starts to feel like analysis, even when it is really just memory plus optimism. Owners do not just estimate value; they attach identity to it. It becomes proof that the years of grind were worth it, proof that they are closer to freedom than they may actually be.

This is not just a math problem. It is an emotional anchoring problem.

Valuation is not a fixed truth. It is a moving range. It changes with interest rates, buyer financing conditions, industry sentiment, and customer concentration. The market does not care what number you got comfortable with; it only cares what a buyer is willing to underwrite today.

“The market does not care what number you got comfortable with. It only cares what a buyer is willing to underwrite now.”

Realistic valuation is not pessimism. It is clarity. It allows you to make better decisions around timing, tax planning, and whether a deal should even happen now. Hope is not useless, it just becomes expensive when it gets mistaken for planning.

One Business, Three Very Different Outcomes
Best Case
  • Ideal buyer fit
  • Strong market
  • Low friction
  • Premium multiple
Friction Case
  • Concentration concerns
  • Weaker market
  • Founder dependence
  • Lower confidence

A realistic range may feel less exciting than a single trophy number. It is also much more likely to help you make a good decision.

Consider two owners who both say their company is worth $15 million. One means: “That is what I need it to be worth.” The other means: “That is one possible outcome inside a range, depending on buyer mix, structure, and timing.” Only one of them is planning.

A useful valuation conversation does not just ask, “What is it worth?” It asks, “What would make it worth more, less, or nothing close to what I am expecting?”

A realistic range is less flattering than a dream number. It is also where better decisions begin.

If your valuation has not been pressure-tested against current market reality and buyer behavior, it is not a plan. It is a placeholder.

Fix the Second Planning Gap

If your exit plan depends on one number being right, it is probably worth pressure-testing the number first.

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