When American Operator brought Matt Carlson on as an Advisor to Greenway Painting, they weren’t looking for someone with a polished playbook. They were looking for someone who had already made the mistakes — and lived to learn from them.

Matt is the owner of M. Carlson Painting, a painting company he built from the ground up in the Twin Cities, Minnesota. Since 2001, he’s expanded into new markets, acquired competitors, survived an office fire, and rebuilt his team more than once. He is, by his own candid admission, a great failure — and that’s exactly what makes him valuable.

Today, Matt sits on the board of Greenway Painting as American Operator’s first-ever advisor to an “operate-to-own” business, holding a partial ownership stake alongside operator Anthony Douglas. His role isn’t ceremonial. He has skin in the game, a standing weekly call with Anthony, and a direct line into every major decision Greenway faces. The goal is simple: help Anthony get to success faster than Matt ever did.

Meet Matt Carlson

Matt didn’t set out to own a painting business. He was 18 years old when a friend’s older brother offered him $6 an hour to paint houses on Lake Minnetonka. He took the job because it was outside, paid cash, and he could work with his friends. He had no painting experience and no intention of making it a career.

But something about the work stuck — not the painting itself, but the business behind it. Working alongside crews and helping with estimates, Matt kept noticing something that would stay with him for decades: the guys running these companies weren’t operating nearly as well as their clients assumed. The bar was lower than it looked, and the opportunity was bigger than anyone seemed to realize.

He kept painting through college, cycling between campuses and jobs, until a single moment changed his direction for good. The summer before his senior year, the bar he’d worked his way up at fired him without warning. He sat in class the first week of school, furious, and made a decision: he was never working for anyone else again. Shortly after, a property management company he’d been courting called with a $25,000 painting job — the biggest he’d ever taken. He picked up his books, walked out of class, and didn’t go back.

What followed was twenty-five years of building M. Carlson Painting the hard way. A business partner who left mid-stride. Crews hired too fast and let go too late. A push into wallpaper installation that was expensive before it became transformative. Every one of those chapters is now material he uses with Anthony.

“I’m a great failure. I can tell you all the different things that didn’t work out. And if I could help Anthony just with the few little things we’ve learned along the way — how to set up his daily tasks, just do all the stuff — this could be a great opportunity.”

Matt Carlson, Advisor, Greenway Painting | Owner, M. Carlson Painting

What Failed Expansion Taught Him

In 2022, Matt made what he now calls one of the biggest mistakes of his career: he opened a second location in Utah, then a third in Indianapolis. Both seemed logical at the time, but failed for the same reason.

Without an owner on the ground — someone with real stakes, real accountability, and real skin in the game — the businesses drifted. Employees had no vested interest in performance. Managers without ownership couldn’t hold crews accountable. The metrics looked fine until they didn’t, and by the time the problems surfaced, the damage was already done. Utah closed. Indianapolis followed.

The lesson Matt took from those years wasn’t that expansion is impossible. It’s that you cannot run a service business from a distance without the right operator in place. That realization is what made American Operator’s model click into focus the moment he heard it.

Becoming an Advisor with American Operator

Matt first connected with American Operator after seeing a LinkedIn post: they were searching for a CEO for a painting company in Jackson, Wyoming. After an initial conversation with the team, it became clear that what Matt brought was something rare and hard to find — the kind of perspective that only comes from building a painting business through every kind of crisis over two and a half decades.

When Anthony Douglas — a former U.S. Air Force Combat Controller with hands-on painting experience — was selected as the operator to run Greenway day-to-day, Matt’s role came into focus. He was the perfect person to serve as an advisor to Anthony and be the experienced voice in his corner as he stepped into ownership for the first time.

For Matt, he understood the opportunity and the value of what American Operator was building — capital to acquire the business, a dedicated operator running it locally, and experienced people providing ongoing support — it was the system he’d been trying to piece together on his own in Utah and Indianapolis and never could.

“You guys taught me what I didn’t know and what I was totally missing — because we were trying to do this without you in Utah and Indianapolis, and it doesn’t work. No matter how hard you try, if you don’t have a candidate like you guys found Anthony, you’re screwed.”

Matt Carlson, Advisor, Greenway Painting | Owner, M. Carlson Painting

Working With the Operator

Matt’s approach to advising Anthony is shaped by the same philosophy that transformed his own business: accountability without comfort, honesty without softness. He learned it himself from a business coach named Dave, who met every complaint from Matt with the same response — “are you done? Here’s what you actually need to do.” That directness, Matt will tell you, is what finally moved the needle.

When he first spoke with Anthony, he didn’t ease him in. He was upfront about how brutal ownership actually is — sleepless nights, no guaranteed income, constant fires, zero margin for wishful thinking. He wasn’t looking for someone who would perform well in a conversation. He was looking for someone who wouldn’t flinch.

Anthony didn’t flinch. He came from the military, was used to being told exactly what needed to happen, and went and did it without needing reassurance. Matt recognized it immediately.

“Talking with Anthony, I was like, all right, this guy’s got it. He is willing to do it. I believe he can do it. He doesn’t need a cheerleader every day. He just needs someone who’s going to talk to him.”

Matt Carlson, Advisor, Greenway Painting | Owner, M. Carlson Painting

From the first kickoff call after Greenway closed, Matt zeroed in on how Anthony was spending his days. It’s the trap every new owner falls into: constant motion mistaken for progress. Matt had Anthony start tracking every hour — what it was spent on, whether it moved the business forward. If you’re picking up paint at Sherwin-Williams, he told him, you’re wasting your time — automate it. If you’re still painting, you don’t have a business — you have a job.

That same directness carries into the day-to-day. When Greenway’s accounts receivable timeline ran long after close — a common pressure point in commercial painting — Matt got on a call and laid out a clear system: require a deposit upfront, know who controls payment at each contracting company, and implement it immediately. 

Beyond the operational guidance, Matt brings something harder to quantify: the ability to recognize patterns before they compound. He watched his own commercial division launch strong and then quietly lose ground as relationships went unmaintained. He knows exactly where the warning signs show up. That means he can name them in Anthony’s business before they become problems.

Getting There Faster

At six months in, Anthony has hit the ground running — expanding into residential work to build cash flow, growing into nearby markets including Driggs and Alpine, and deepening commercial relationships across Jackson. 

For Matt, the measure of success isn’t a revenue milestone. It’s watching Anthony reach the point of stability — debt paid down, systems in place, team running well — in a fraction of the time it took Matt to find solid footing. The first 90-days of a transition is one of the most critical times for a new business owner and Matt wants Anthony to wake up and feel like he’s doing it. Not someday, but as quickly as two years.

“You’ve got to put your ego aside, because you can’t do this all alone. It’s going to take you years of trial and error. But if you want to get there faster — my goal for Anthony is to help him get his debt paid off in a fraction of the time.”

Matt Carlson, Advisor, Greenway Painting | Owner, M. Carlson Painting

What makes that possible isn’t just the advisor relationship. It’s the complete system behind it: the capital to acquire a business of Greenway’s caliber, an operator with the character and discipline to run it, and experienced guidance from someone who has already navigated everything Anthony will face. Each piece matters and all three together is what sets the trajectory.

“Without me, he could probably do it. Without you, he could probably do it. But you put these two together — and you have that right person in Anthony — it can’t fail. It’s not going to be easy. But he’s going to be so successful.”

Matt Carlson, Advisor, Greenway Painting | Owner, M. Carlson Painting

Matt Carlson’s partnership with American Operator and Greenway Painting reflects our commitment to building the infrastructure that local ownership requires — not just the capital to acquire a business, but the experience, accountability, and ongoing support to help it grow. For Anthony, having Matt in his corner means the costly detours that come with going it alone don’t have to define his path.

If you are a seasoned operator ready to lend your experience to the next generation of local business owners, learn more about becoming an advisor.

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