Roofing contractors should begin planning three to five years in advance for their exit if they want to avoid wasted time and money.

How Would I Exit Roofing in 2025

Kevin Kennedy shares what he would do when planning to exit a roofing company in today’s business climate

In the late 1990s, our management team spent six years and over $250,000 navigating the exit path due to fragmented advice. We ultimately executed a structured management buyout from 2003 to 2013.

The landscape looks entirely different, with new options and advanced strategies now available to contractors.

Here, I share my personal story and lessons learned as both a business owner and a sell-side M&A advisor. Ultimately, I’ll outline exactly how I would exit the market today, knowing what I know now.

A Fourth-Generation Legacy

This story is told from my perspective, as one of three majority owners who exited the company.

In the mid-1980s, I began a buyout of a third-generation commercial roofing company with two other associates. Our team took control in 1995, after a nine-year management buyout (MBO) from the founder’s son. He had wisely implemented a succession plan focused on quality, safety, and customer satisfaction — a legacy that continues to define Evans Roofing today.

During the late 1990s, consolidators were knocking at our door, fueled by Y2K, the Federal Reserve, and the tech boom. We explored multiple offers, including those from two consolidators, a national M&A advisor, an ESOP structure, and ultimately, an MBO. By 2003, we committed to an internal transfer of five senior managers.

The Price of Fragmented Advice

Between 1997 and 2003, we spent six years and more than $250,000 navigating the exit process. As three owners with different goals, we received disjointed advice from attorneys, CPAs, financial advisors, and estate planners — none of whom coordinated with each other.

The result? Wasted time and money, unnecessary taxes, and a plan full of missed opportunities.

Exit Lessons Learned

1. One Plan Doesn’t Fit All: We were three different owners with three different goals and timelines. Every successful exit plan must be tailored to meet each owner’s personal, financial, and business needs.
2. Consolidators Come and Go: In the early 2000s, four major roofing consolidators were active. After the tech crash, only Tecta America survived. Today, it’s the number one industry leader by revenue.
3. Clarity Drives Action: Once we agreed on a shared vision, we focused on internal succession. A clear path helped us avoid distractions and stay committed to our MBO.

From Contractor to Exit Planner

After retiring in 2008, I found myself fielding questions from business-owner friends seeking guidance. What started as casual conversations became a calling.

I earned exit planning certifications and launched Beacon Exit Planning. I quickly realized how often other contractors waste millions due to poor, fragmented, or generic cookie-cutter advice. That insight motivated me to speak, write, advocate for, and guide other owners.

In 2011, I partnered with Joe Bazzano, a CPA and tax strategist who brought deep technical expertise across valuation, legal, asset protection, tax mitigation, insurance, and estate planning disciplines.

Together, we’ve implemented more than 60 exit plans in the past 16 years — each tailored to reduce risk, build business value, and align the owner's business, personal, and financial outcomes.

What I’d Do in 2025

If I were exiting today, here’s how I’d do it:

1. Start Three to Five Years Ahead: I’d develop a strategic exit plan well in advance, defining goals, obtaining a valuation, cleaning up financials, and strengthening management. It takes time to align the company and management with the chosen exit path.
2. Lead with Clarity, Not Emotion: The plan would be driven by the owner's goals, not unsolicited offers. I’d avoid rushing into a deal or relying on fragmented advice.
3. Explore External Buyers: Today’s private equity firms and consolidators are more sophisticated and better capitalized. I’d explore both, weighing deal structures, culture, and long-term alignment.
4. Create Competitive Tension: I would never engage with one buyer in isolation. A structured, competitive process creates options, leverage, improves terms, and increases enterprise value.
5. Mitigate Taxes — Early: I’d engage a tax strategist at least 12–24 months before the sale. Techniques such as entity structure, installment sales, asset allocation planning, charitable giving, and proper utilization of the U.S. tax codes can significantly reduce or eliminate capital gains and income taxes — but only if structured before the closing.

Final Thoughts

Our team successfully transferred the business, but at a cost: millions in unnecessary taxes, stress, and avoidable delays. The 2025 market offers a wider range of tools, buyer options, and tax mitigation strategies for both residential and commercial roofers than ever before.

With proper preparation, owners today can exit with greater control, clarity, higher EBITDAs, and wealth preservation.

The information provided is not intended to be legal, accounting, insurance, or tax advice. Beacon is a process consultant that provides written plans, consulting, and support programs to private owners for succession and exiting their businesses.