When did you first realize you were an entrepreneur?
That's the question I love asking every guest on Today's Business Leaders, and Brian Roach's answer hit home in a way that made me smile.
"When every place I went to work, I just kept finding problems and pointing out to people different directions they needed to go."
Sound familiar?
If you're an entrepreneur reading this, you probably nodded your head. We're the ones who can't help but see what's broken and imagine how to fix it. Sometimes people listen. Sometimes they don't. And eventually, we realize we need to control our own destiny.
The Insurance Years: Learning to Spot BS Early
Brian's journey started right out of Marietta College in 1989. He landed at a small insurance agency in Barberton, Ohio, working for a friend who was mostly an absentee owner.
The setup was perfect for a young entrepreneur: they plugged him in as "the fresh blood with the college education" and told him to help build the business doing claim processing for health insurance.
Things were going well. The business was growing. Brian was crushing it with cold calling and sales.
And then the minority owner hired his mom. And then his daughter.
Here's where it gets good.
The majority owner (Brian's friend) came to him confused: "The business is growing, but it's not profitable. What's going on?"
Brian saw it immediately: "Your partner has no incentive for it to be profitable. He's 75% owner, you're 25%. So he can hire his mom and daughter, they make money, but so what? There's no profit share."
Brian told him straight up: "Don't throw me under the bus. Figure this out on your own."
What does his friend do? Throws him under the bus immediately.
Three days later, the minority owner said they didn't need Brian anymore.
But here's the beautiful part — several clients had grown to trust Brian so much that they called the majority owner and said: "If Brian's not back, we're moving our business."
Brian got to come back. But not in the same role. Just long enough to find another job.
Lesson learned: Client relationships are gold, and nepotism is expensive.
The Corporate Grind and the Broken Promise
Brian moved into the big leagues next — Altman Hospital and their health insurance division, Altcare.
He was the first outside sales rep they hired with actual health insurance experience. Naturally, he started asking questions like "Why aren't you doing this?" and "Why aren't you doing that?"
The response? "We're a hospital."
Brian's thinking: "That's not what this product is."
Within his first nine or ten months, he was crushing his sales numbers. Then the VP of sales pulled him aside with some news:
"You're doing great, but we're going to have to change your compensation. At the pace you're going, you're going to be making more than the president of the hospital."
Let me pause here for a second.
If you're reading this and you've ever been told you need to make LESS money because you're too successful at sales... you know exactly how infuriating this is.
In sales, you WANT your salespeople making bank. That means everyone's winning.
But corporate doesn't always get it.
They hired two inexperienced people, put everyone on team bonuses instead of commission, and Brian hit his sales bonus in January — one month into the year. The team bonus was at 90% from his work alone.
The other two were going to get the same bonus for doing nothing.
Brian's response? "This ain't working. I'm going to go eat what I kill."
Smart move.
The Partnership That Wasn't
Brian found an agency that promised him a path to partnership. They laid out clear parameters: hit these numbers in two years, and you're in.
Two years later, Brian hit the numbers.
Their response? "Well, we need a little time. And by the way, you're coming onto the debt too."
Translation: You get to inherit the debt of the retired guy who has a chauffeur and hired his son.
Hard pass.
Brian and a couple other team members decided to leave and start their own partnership. Three people. Fresh start.
Fast forward a couple years — they're all making six figures. Things are looking good. Brian's ready for the next level of growth.
He tells his partners: "We need a property and casualty agency to diversify. And we need a computer on every desk."
The year? This was back when having email on every desk wasn't standard yet.
The cost? $21,000 total.
His partners looked at each other and said: "That's $7,000 I could take home."
They outvoted him 2-1.
No computers. No diversification. No vision.
Eventually Brian sold his stake to his two partners. The business still exists today — probably still without enough computers.
The Roofing Pivot: When Friends Ask for Help
After bouncing through a few more roles (including a stint hiding at Citizens Bank with a VP title and salary), a couple of friends approached Brian about joining their roofing and restoration business.
Brian's first response? "I have no interest in knocking doors and storm chasing."
But his friends were smart. They'd just won a lawsuit, got an influx of cash, but had to change their company name. They needed someone to handle marketing and sales.
Brian saw the opportunity to do what he's always been good at: marketing and branding.
He joined as marketing manager and sales manager. And immediately, he reframed the business.
"Storm chasing has a negative connotation," he told them. "Let's do locally what we do after storms, but with the same skill set. We won't always be as busy, but if you're selling brand, quality, and consistency, you can do retail work too."
They listened. And it worked.
But then they wanted Brian to go 100% commission. No more salary.
He hated it at first. But it turned out to be one of the best things that ever happened to him.
The $345 Roof "Tune-Up" That Changed Everything
Going full commission forced Brian to work smarter, not just harder.
Instead of knocking doors like the other storm chasers, he went to insurance agents.
He told them: "I'll tell you the truth. If your customer calls, I'll look at their roof and tell you whether they should file or not."
The agents started trusting him.
And here's the story that proves why:
An elderly gentleman in his late 80s with terminal cancer called his agent. A storm chaser had told him he needed to file a claim for roof damage.
The agent called Brian.
Brian got on the roof. It was a stick. Just a stick on the roof that looked like a damaged shingle.
He went down and told the man: "Your roof's perfectly fine."
The man said: "I just want to do something for peace of mind. I don't want to leave my wife with problems."
Brian made something up on the spot: "We'll do a 'roof tune-up.' We'll go over everything, seal loose shingles, check the flashings."
They charged $345.
Nothing. But it gave the man peace of mind.
And that agent? He sent Brian to every legitimate opportunity after that because he knew Brian would tell the truth.
That's how you build a business that lasts.
Eventually, Brian's partners sold the business (they had rental properties and their kids were getting older). The new owner took care of Brian with retention bonuses — $10,000 every six months from the old owners, $10,000 from the new owner.
$40,000 a year just to stick around and provide stability.
The Lesson: Entrepreneurship Isn't for the Faint of Heart
Brian's journey is a masterclass in resilience, integrity, and knowing when to walk away.
He got thrown under the bus. He got his compensation cut for being too good at sales. He got outvoted on basic technology investments. He learned the hard way that partnerships need clear, aligned vision.
But through it all, he kept showing up. He kept finding problems. He kept solving them.
And he built relationships that outlasted every corporate BS move, every bad partnership, and every short-sighted decision.
If you're an entrepreneur, you've probably lived some version of Brian's story.
The key is to keep going. Keep learning. Keep building relationships. And never stop trusting your instincts when you see a better way forward.
Want to connect with Brian Roach or learn more about Always Be Fair Roofing?
Visit: https://www.alwaysbefairroofing.com/
If you're in Northeast Ohio and need honest, quality roofing work from someone who actually gives a damn about doing the right thing — Brian's your guy.
This conversation is from the Today's Business Leaders podcast. If you want to hear more stories like Brian's, subscribe wherever you listen to podcasts.
