🎙SMB15: From Bartender to Business Owner: Matt Carlson’s Journey in Residential Painting

This is SMB15, a rapid-fire interview series featuring small business owners, investors and service providers. We dig into different industries, business models, and SMB topics. Hosted by Will Fry, founder of Mainshares.

Listen now on Spotify or YouTube.

From getting fired as a bartender to running a multi-crew painting company, Matt Carlson has seen it all. In this episode of SMB15, Matt shares the raw story of building M. Carlson Painting over 25+ years: the mistakes, the systems, the culture, and why reputation is the only real warranty in business.

Some takeaways:

1. Paying your guys more lets you demand more of them. Matt pays his crews above-market rates, but in return sets higher expectations for quality, professionalism, and communication. This creates loyalty and raises the performance bar, ultimately making crews better painting companies in their own right.

2. Beware of expanding into unfamiliar markets. Matt entered Utah with confidence after success in Minnesota, only to find that homeowners there weren’t nearly as “house proud” as Minnesotans. They were often trying to find the cheapest contractor and cared less about high quality paint jobs for their multimillion-dollar homes. He now sees adjacent markets as a smarter first move and has found Indianapolis to better mirror the market dynamics of Minneapolis.

3. No one disrespects you. As part of M Carlson’s culture, the crews know that Matt has their back. This further drives loyalty and retention of the painters. In fact, they recently bailed out of a $45K job when a client consistently treated his crews like garbage.

4. Exterior painting is a seasonal business in Minnesota. Minnesota winters shut down exteriors, so Matt sought out apartment turns, insurance work, and contractor jobs to smooth cash flow. Relying on one type of work would have left the business vulnerable and ratcheted up the pressure on summer months to maximize cashflow.

5. Make mistakes fast, then learn. Matt’s advice to new entrepreneurs: document your lessons, avoid emotional decisions, and accept that mistakes are inevitable. The goal isn’t perfection, but rapid learning and consistent effort.

6. Find your “why” to endure hard times. Running a small business is all consuming and stressful. Matt shared numerous times when he wanted to throw in the towel and go back to just doing small jobs with his friends. Matt trudged on because of his “why” - never want to work for someone else after his experience working that bar in college.

Where to find Matt and M. Carlson Painting:

• LinkedIn: https://www.linkedin.com/in/matthewcarlsonorono/

• Website: https://www.mcarlsonpainting.com/

In this interview, we discuss:

• 0:00 Final Tipping Point

• 1:38 Going All-in on Painting

• 2:56 Building Trust with Clients

• 5:33 Why Communication Sets You Apart in the Trades

• 7:51 Intro to Matt Carlson

• 9:30 First Year of a Minnesota Winter

• 13:50 Specializing Crews by Project Type

• 16:21 Splitting Into Residential, Contractor, and Commercial Divisions

• 19:20 Pay More than Anyone Else

• 22:58 No One Disrespects You

• 25:56 A Warranty Is Your Reputation

• 28:55 Expanding Beyond Minnesota: Utah & Indianapolis

• 34:44 Advice for New Small Business Owners