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Overview: Most entrepreneurs don’t think seriously about selling their business until a buyer shows up.
Jonathan Sherrill learned how buyers think years before he ever became a seller.
Before founding Quicken Steel, Jonathan spent six years running his family’s roofing supply company after it was acquired by private equity. That experience gave him a front-row seat to what investors actually look for once they own a business.
He saw the importance of systems.
He saw the importance of leadership.
He saw the importance of building a company that could grow without depending on one person.
Those lessons shaped every decision he made when he launched Quicken Steel.
Just four and a half years later, he sold the business for roughly double what he originally expected, with no earnout and no transition period.
Throughout his conversation on the Make BIG Happen Podcast, Jonathan shared what private equity taught him, why his daughter’s autism diagnosis changed the way he defined success, how executive coaching prepared him for one of the biggest decisions of his career, and why the strongest businesses are built long before they’re sold.
Private Equity Taught Him What Buyers Really Want
Growing up in a family business, Jonathan learned the importance of customer service, hard work, and entrepreneurship.
Working under private equity gave him an entirely different perspective.
For six years, he experienced what buyers care about after the acquisition.
Every week brought new conversations around systems, processes, leadership, KPIs, and accountability. The focus wasn’t simply on running the business day to day. It was on building an organization that could continue growing without constant involvement from the owner.
When Jonathan started Quicken Steel, he carried those lessons with him.
Instead of waiting until he wanted to sell, he intentionally built the company the way he had seen sophisticated buyers evaluate businesses.
Key Takeaway: The best preparation for an exit starts years before you ever decide to sell.
Build a Business That Doesn’t Depend on You
Jonathan didn’t want to build a business where everything relied on him.
He focused on putting the right people, systems, and processes in place so the company could continue operating without the founder making every decision.
Near the end of the conversation, Jonathan shared what he believes is one of the first questions every buyer asks:
If you’re no longer in the business, what happens to the business?
His goal was to make sure there was a great answer.
By building a company that could operate independently, he wasn’t just preparing for an eventual sale. He was building a stronger business every day.
Key Takeaway: Businesses become more valuable when they can succeed without depending on the founder.
Know Why You’re Building
One of the most personal moments of the conversation centered on Jonathan’s daughter, Faith.
When she was diagnosed with autism at two years old, his priorities changed.
He began thinking beyond building a successful company.
He wanted to create long-term security for his family.
He wanted the flexibility to be present when his daughter needed him.
He wanted to know she would always be taken care of.
That clarity became his motivation.
As Jonathan shared, if Faith needed him, whatever business issue he was working on could wait.
His business existed to support what mattered most. Not the other way around.
Key Takeaway: Knowing why you’re building the business makes it easier to make the decisions that matter most.
A Great Coach Brings Perspective
Jonathan started working with CEO coach John Giegerich before selling the business was even part of the plan.
As the company grew rapidly, John became a steady voice during an increasingly demanding period.
When Jonathan later decided to pursue a sale, that relationship became even more valuable.
John wasn’t simply there to offer advice.
He challenged Jonathan when necessary.
He wasn’t afraid to disagree.
He helped him think through difficult decisions.
He introduced him to Andy Harris at STS Capital, who ultimately helped guide the transaction.
Looking back, Jonathan said he wouldn’t go through another sale without a coach.
Having someone with experience who isn’t emotionally tied to the outcome made an enormous difference.
Key Takeaway: During major decisions, a trusted coach provides perspective that’s difficult to create on your own.
The Exit Process Is Harder Than Most Founders Expect
Jonathan was candid about one part of selling a business that entrepreneurs rarely talk about.
Due diligence.
While buyers were evaluating the company, the business still had to perform.
Customers still expected results.
Employees still needed leadership.
At the same time, buyers were requesting documents, asking questions, reviewing financials, and evaluating every part of the organization.
Jonathan described the process as emotionally draining because until the funds are wired, nothing is guaranteed.
Even closing day brought unexpected stress when paperwork related to a charitable donor-advised fund delayed the transaction by several days.
Looking back, Jonathan says the preparation done years before the sale made navigating those moments much easier.
Key Takeaway: Selling a business isn’t just about finding a buyer. It’s about building a company that can withstand the demands of the sale process itself.
Life After the Sale
Jonathan also spoke openly about something many founders don’t expect.
What happens after the deal closes.
After working continuously since he was fourteen years old, the silence was unfamiliar.
The emails stopped.
The phone stopped ringing.
The responsibility of running the business was suddenly gone.
Rather than rushing into another venture, Jonathan chose to focus on what had motivated him from the beginning.
He moved back to Florida.
He spent more time with his family.
He eventually co-authored The Extraordinary Exit to help other entrepreneurs better understand the journey of selling a business.
For Jonathan, the sale wasn’t the finish line.
It created the opportunity to spend more time on what mattered most.
Key Takeaway: A successful exit isn’t just about selling the business. It’s about being intentional about what comes next.
Final Thought
Near the end of the conversation, Jonathan shared what one decision every CEO should make today if they hope to walk away someday with no regrets.
His answer reflected the lessons he’d learned throughout his career.
Think like a buyer.
Build systems.
Develop people.
Create a business that doesn’t depend on you.
Those principles didn’t begin during the sale process.
They shaped the business from the very beginning.
Jonathan’s story is a reminder that buyers aren’t simply purchasing financial results.
They’re investing in a business that can continue succeeding long after the founder steps away.
Listen to the full Make BIG Happen Podcast episode with Jonathan Sherrill here.
About CEO Coaching International
CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, the firm has coached more than 2,000 CEOs and entrepreneurs across 100+ industries and 90 countries. Its coaches—former CEOs, presidents, and executives—have led businesses ranging from startups to over $10 billion, driving double-digit sales and profit growth, many culminating in eight, nine, or ten-figure exits.
Companies that have worked with CEO Coaching International for two years or more have achieved an average revenue CAGR of 22.8%, nearly 2X the U.S. average, and an average EBITDA CAGR of 37.5%, nearly 3X the national benchmark.
Discover how coaching can transform your leadership journey at ceocoachinginternational.com.
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