Home News & Insights Avoiding Common Mistakes in Middle-Market Transactions
October 21, 2025
Avoiding Common Mistakes in Middle-Market Transactions
By Michael Lynch

Valuing a middle-market company is often more art than science. Unlike large-cap transactions, where abundant data and market comparables simplify the process, middle-market valuations come with nuances that require careful judgment. Yet, many investors and business owners fall into predictable traps that distort value, sometimes leading to overpayment, missed opportunities, strained deal negotiations, or mismatched expectations between the seller and buyer.

At Harney Capital, we’ve seen that the most successful transactions are grounded in disciplined, well-reasoned valuations. In this article, we outline common valuation mistakes in the middle market and how to avoid them, enabling both buyers and sellers to make informed decisions and achieve better outcomes.

1. Over-Reliance on Multiples

Many transactions lean too heavily on EBITDA or revenue multiples derived from public comps or precedent transactions. While multiples offer a quick benchmark, they often fail to capture differences in growth prospects, customer concentration, margin stability, or operational scalability. A $500 million public company trading at 10x EBITDA is not directly comparable to a $40 million private business.

How to Avoid It:

Use multiples as a starting point, not the final word. Adjust for company-specific risk factors, and consider using a triangulation approach by comparing multiple valuation methods to arrive at a more defensible valuation range.

2. Ignoring Industry and Market Trends

A business thriving today may face headwinds tomorrow. Valuations that overlook emerging industry shifts such as technology disruption (Blockbuster vs Netflix), regulatory changes, or evolving consumer behavior can quickly become outdated.

How to Avoid It:

Incorporate a forward-looking lens. Conduct thorough industry research, monitor M&A trends, and evaluate how external forces could impact future cash flows or multiples. A seemingly small market shift (e.g., automation, telehealth, or ESG compliance) can materially affect long-term value.

3. Inadequate Normalization of Earnings

Many mid-market businesses have non-standard accounting practices, such as owner compensation, personal expenses, or one-off adjustments that skew reported earnings. Failing to normalize these figures properly leads to misleading valuation conclusions.

How to Avoid It:

Perform a robust quality of earnings (QoE) analysis. Adjust for non-operational items and non-recurring revenue or expenses. This ensures that the valuation reflects the company’s sustainable earning power rather than accounting artifacts. Transparency and consistency in normalization build buyer confidence.

4. Overlooking Working Capital Needs

Buyers and Sellers often focus on EBITDA but ignore the cash tied up in working capital. Overestimating free cash flow by neglecting working capital swings can inflate valuations and create friction during deal negotiations.

How to Avoid It:

Analyze historical working capital trends and industry norms. Include a working capital adjustment in your purchase price mechanism to ensure both parties align on normalized levels. Remember: growth usually consumes cash before generating it.

5. Misjudging the Company’s Risk Profile

Treating a private, middle-market business like a large public company underestimates its unique risks, including limited liquidity, customer concentration, and dependence on key individuals.

How to Avoid It:

Buyers will use appropriate risk premiums to reflect company-specific challenges, use higher discount rates for smaller or less diversified businesses, and document the rationale behind every adjustment. Sellers should mitigate these risks by bolstering weaknesses. For example, executing long-term contracts, demonstrating growth potential, and hiring industry leaders who are compensated for performance and have a vested interest in staying with the company through the sale. Recognizing risk upfront helps avoid painful repricing later.

6. Ignoring Non-Financial Value Drivers

Valuation exercises sometimes overlook intangible assets like brand reputation, employee expertise, proprietary processes, or customer relationships – especially when these aren’t captured on the balance sheet.

How to Avoid It:

Incorporate qualitative assessments into the valuation framework. During management discussions, probe for cultural strengths, operational efficiencies, and intellectual property advantages that can justify premium pricing or defensibility.

7. Overestimating Synergies

Buyers often justify aggressive pricing with expected synergies, cost savings, cross-selling opportunities, or operational efficiencies that may never materialize.

How to Avoid It:

Base synergy estimates on detailed integration planning and verified data. Use conservative assumptions, stress-test scenarios, and clearly separate standalone valuation from synergy-driven value.

8. Neglecting Scenario and Sensitivity Analysis

Relying on a single “base case” forecast ignores the inherent uncertainty of middle-market businesses, which are often more vulnerable to market shifts.

How to Avoid It:

Build multiple valuation cases based on optimistic and downside scenarios, and run sensitivity analyses around key variables (growth rate, margins, discount rate). This approach not only improves accuracy but also prepares both buyer and seller for negotiation flexibility.

Building a More Defensible Valuation

 Accurate valuations aren’t just about math; they reflect understanding, discipline, and market insight. The best middle-market valuations:

  • Triangulate methods: Combine DCF, comparable companies, and precedent transactions.
  • Normalize with care: Be transparent with add-backs and adjustments.
  • Apply risk premiums appropriately: Recognize smaller-company realities.
  • Test assumptions: Use scenario planning to anticipate surprises.

A defensible valuation doesn’t aim for perfection; it aims for credibility. It’s the foundation on which fair negotiations and successful deals are built.

We believe the best valuations are those that are the most credible, defensible, and thoroughly thought through. Our team combines financial analysis, sector insight, and transaction experience to help clients navigate the nuances of middle-market value and maximize outcomes.

If you’re considering a transaction or want a second opinion, reach out for a confidential discussion to ensure your business value reflects its true potential.

Michael Lynch
Michael Lynch
Associate

Michael has diverse experience in financial services and investment banking with specialization in M&A, real estate, data analysis and project management. At Harney, he supports client engagements and transactions with…Read More