Middle-Market Business Owners: What’s Your Endgame?

By Jeffrey Lewis, David Dinolfo, on July 21st, 2025

For many middle-market business owners, their company is more than a livelihood, it’s a legacy. But what happens when it’s time to move on? Whether your exit is years away or just around the corner, the most successful transitions begin with a clear endgame in mind. That means thinking like a buyer, planning early, and building a business that thrives without you.

Succession Planning: Securing the Future

Succession planning is often overlooked until it’s too late, but it’s one of the most critical components of a successful exit strategy. Whether you plan to sell to a third party, transition to family members, or promote from within, a well-thought-out succession plan ensures continuity, preserves value, and protects your legacy.  Succession planning isn’t just about preparing for an exit; it’s about building a resilient business that can thrive for generations to come.

Create Long-Term Business Value

Selling a business is not a transaction, it’s a process. And for most owners, it’s a once-in-a-lifetime event. The earlier you begin preparing, the more options you’ll have and the more value you can unlock. A well-prepared business commands higher valuations, attracts more buyers, and gives you greater control over the terms of your exit.

Buyers evaluate businesses based on both quantitative and qualitative factors. Here are five key value drivers that can significantly impact your company’s worth:

1. Clean Financials & Operational Housekeeping

Buyers want confidence in what they’re acquiring. That means GAAP-compliant financials, reliable internal controls, documented procedures, and organized records. Think of it as staging your business for sale, just like you would a home.

2. Strong, Independent Management Team

A business that runs smoothly without the owner is far more attractive. Buyers look for leadership teams with defined roles and minimal reliance on any one individual.

3. Diversification

Overdependence on a single customer, product, or supplier is a red flag. Spread your revenue across multiple channels and ensure your supply chain is resilient.

4. Consistent Growth & Upside Potential

Buyers pay premiums for businesses with a track record of growth and clear opportunities for expansion. If your business is growing—and can keep growing—it’s worth more.

5. Competitive Buyer Interest

The presence of multiple interested buyers creates a private auction environment, driving up price and improving terms. This is where experienced investment bankers add tremendous value.

Build for the Exit, but Benefit Today

Here’s a powerful truth that’s often overlooked: the same improvements that make your business more attractive to buyers also make it more enjoyable, profitable, and resilient to own right now.

Think about it:

  • Clean financials don’t just impress buyers; they give you better visibility and control.
  • A strong management team doesn’t just reduce owner dependency, it frees you up to focus on strategy, growth, or even take a vacation.
  • Diversified revenue streams don’t just reduce buyer risk; they protect your business from shocks and downturns.
  • Documented systems and processes don’t just streamline due diligence, they reduce chaos, improve efficiency, and make onboarding easier.

In other words, preparing your business for a future sale is not just about the end, it’s about improving the journey.  So even if you’re not ready to sell, ask yourself: “If I were buying this business today, what would I want to see?” Then start building that business—for your future buyer, and for yourself.

Ready to Take the First Step? Start with a Go-To-Market Assessment

If you’re serious about maximizing the value of your business and exiting on your terms, the smartest move you can make today is to see your company through the eyes of a buyer.

A Go-To-Market Assessment is your strategic starting point. It’s not a valuation in theory, it’s a real-world, market-based analysis that evaluates your business the way potential buyers will. This assessment helps you:

  • Identify your company’s key strengths and valuation enhancers
  • Uncover hidden risks or detractors that could reduce buyer interest
  • Understand how your business stacks up in today’s M&A market
  • Receive a realistic valuation range based on current market multiples
  • Get actionable recommendations to improve your business’s marketability

Think of it as a dress rehearsal for your future exit—one that gives you time to fix what’s broken, enhance what’s working, and position your business to command top dollar when the time is right.

Final Thoughts

If you’re a middle-market business owner, you should frequently ask yourself the question “What’s my endgame?” Whether your exit is imminent or years away, now is the time to start thinking like a buyer and positioning your business for the future. With the right preparation, guidance, and mindset, you can turn your life’s work into a lasting legacy—and a successful transition.

If this topic is interesting to you, we invite you to download our guide, “A Business Owner’s Guide to Middle-Market M&A.”   This guide is specifically designed to introduce business owners to middle-market mergers and acquisitions (M&A) and help them understand the basics of long-term exit planning. Whether you are in the early stages of considering selling your business or have already begun the process, this guide will equip you with the basics.

This material has been prepared for general, informational purposes only and is not intended to provide, and should not be relied on for, tax, legal or accounting advice. Should you require any such advice, please contact us directly. The information contained herein does not create, and your review or use of the information does not constitute, an accountant-client relationship.

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