How Middle Market CEOs Should Think About Exit

April 23, 2026

I’ve bought 100+ companies. The best deals I’ve done are the ones where the seller started preparing two years before they hit the market. The worst are the ones where they started two months before.

The discount for being unprepared

A well-prepared middle market company sells at a premium multiple. An unprepared one sells at a discount — often 2-3 turns of EBITDA lower. On a $20M EBITDA business, that’s $40-60M in value. Left on the table because nobody started early enough.

The two-year checklist

Financials auditable back three years. Customer concentration below 30%. Leadership team that can run the company without the founder. Documented processes. A recurring revenue story or customer retention data. These aren’t nice-to-haves. They’re the difference between top-quartile and bottom-quartile multiples.

The mindset shift

Exit isn’t an event. It’s a state the company should be in continuously. If you could sell tomorrow at full value, you’re running a great company. If you can’t, you’re running one with a ceiling.

When to start

The right answer is now — regardless of whether you plan to sell in two years or twenty. The disciplines that prepare a company for exit are the same ones that make it run better today.

Ready for a direct conversation about your business?

Bill Canady takes a limited number of strategy coaching calls each month with middle market CEOs, founders, and owners who want a direct read on where their company stands and what to do next. No pitch. No fluff. One honest conversation about growth, profitability, and exit readiness. Book your strategy coaching call at billcanady.com.

About the Author

Bill Canady

Bill Canady is a national best-selling author, Founder & CEO of The 80/20 Institute, and a global business leader known for transforming companies into high-performing, profitable enterprises. Over the course of his career, Bill has led multibillion-dollar organizations through their most critical challenges—navigating complex regulatory, investor, and media environments—while consistently delivering profitable growth.

Drawing on decades of executive experience, Bill created the Profitable Growth Operating System (PGOS), a proven framework designed to help leaders cut complexity, focus on the critical few, and accelerate growth. Through The 80/20 Institute, he and his team partner with CEOs, executives, and entrepreneurs worldwide to apply the 80/20 methodology in real-world settings, unlocking revenue growth, margin expansion, and shareholder value.

As both an operator and advisor, Bill’s mission is clear: to give leaders the tools, systems, and confidence they need to achieve sustainable, profitable growth — without sacrificing focus, culture, or execution.

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