SMB15

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. smb15.substack.com

Episodes

August 20, 2025 38 mins

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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:

* Paying your guys more lets you demand more of them. Matt pays his crews above-mark...

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When COVID hit, Ryan Baskins was selling HVAC systems to hotels — not a great place to be. Over beers with a friend, he had a realization: 3D printing had finally gotten good enough to launch physical products without a factory. That spark led to Chatelet Manufacturing, a fast-growing additive manufacturing business with 80 printers and a thriving B2B and consumer arm.

In this episode, Ryan breaks do...

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Julia Callahan quit a stable career in medical sales to knock on doors with a handwritten notebook. Less than a year later, she’s grown Jubilee Cleaning Services to 17 employees and $70K/month in revenue. What started as a low-overhead side hustle has become a full-time mission — delivering dignity through cleaning while building an operation that can scale.

In this episode, we cover how Julia priced...

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Ryan Robinson didn’t grow up dreaming of shingles. But after working in transportation and getting laid off during a downturn, he fell into roofing — and never looked back. Today he’s the co-owner of Upright Roofing and Construction, one of the fastest-growing roofing businesses in the Dallas-Fort Worth area. Along the way, he’s also built a paintless dent repair shop and a Christmas lights business...

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After 14 years as a railroad engineer, Scott Gunter bet the house — and $116K — on a single container of packaging from a Chinese supplier he’d never spoken to. That gamble paid off. Today, he runs JarCo, a growing print and packaging business in Arkansas with clients in food & beverage, schools, and beyond.

In this episode, we get into what it takes to run a hybrid printing and packaging company, fr...

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California has 6,000 metal fabrication shops and very few successors to run them. Jules Brenner is on a mission to fix that. Through Industrial Succession, he’s buying and operating metal fabrication shops that serve time-sensitive and highly engineered use cases — from data centers to critical infrastructure.

In this episode, Jules shares what makes the succession problem particularly challenging i...

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After stints in investment banking and private equity, Chris acquired System Six in July 2021, a remote accounting firm serving SMBs. He doubled the team, expanding into payroll and tax, and built a fully remote operation spanning 25+ states and 3 countries. Along the way, he's been active in the Entrepreneurship through Acquisition (ETA) community, frequently speaking at and sponsoring conferences.

...

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Many assume print is dying, but Connor Pera would disagree. After acquiring The Print Authority, he found a surprisingly durable and fragmented market filled with sticky B2B relationships and reoccurring demand. With a speciality in web-to-print services, Connor is on track to clear $3M in revenue in his third year of ownership.

In this interview, we dive into the mechanics of web-to-print services, ...

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Paul never saw himself installing fences. After serving in the Marines straight out of high school, he joined the upper echeleons of finance at Blackrock, but something was missing. Once thing led to another and he left his career in finance behind to start a fencing company with his friend. Three years later, Hawk Fences is installing 15 fences a week for a mix of residential and commercial custome...

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Kyle has built the WeBuyUglyHouses of the floral industry. He won't pay top dollar, but he'll give retiring owners cash at close and let them drop the keys and walk into the sunset. What happens next is the product of dozens of acquisitions and treating flower shops like assembly lines.

In this interview, we dive into his journey to developing a dialed playbook for operating best-in-class flower sho...

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What does it take to build a vacation rental management company from scratch? Franklin Dusserre walks us through his journey building French Cowboys Management. What began as helping a few friends manage their Airbnb listings turned into a leading vacation rental management company in Austin, TX.

In this interview, we dive into the Golden Age of Airbnb, the changing regulatory landscape, and the tac...

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John started in debt collections right out of college. Staked by his former boss in his late 20s to buy his first agency, he's spent the last two decades quietly scaling in a misunderstood industry. Today, he runs a national network of 16 collection agencies serving hospitals, banks, and utilities across the country.

In this interview, we go deep on what most people don't understand about the collect...

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Shawn Allard is the owner of Novel Ice Cream, a multi-location ice cream shop in Phoenix known for its inventive flavors and standout branding. After starting his career in dental consultancy, Shawn knew he wanted to find a more entrepreneurial path. He discovered the entrepreneurship through acquisition (EtA) world on Twitter. Within a year, he acquired Novel Ice Cream, then a two-unit operation in...

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Kyle Miller is part of a third-generation family business that started in the 1950s supplying parts to ships in the Port of Detroit. Fast forward 70 years, the company is now headquartered out of Charlotte, NC and primarily focuses on distributing fasteners across a wide range of applications. In this episode, we get into the history of Bamal Fasteners, life working with your brother and father, how...

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After working on the family business with his father, Matt Railla joined Transworld business brokerage in Los Angeles. But he didn’t stay there for long. In 2024, he bought one of his own listings: Top Termite Co. He’s now the owner-operator of a trusted termite inspection business in California, doing over 1,500 inspections a year. In this interview, we discuss how Matt Railla transitioned from bro...

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Bob Frisch grew up in the family business, helping his dad demolish pools across Southern California. Today, he’s at the helm of Frisch & Sons, the leading pool demo company in Orange County. With small lots and the rising popularity of ADUs, Frisch & Sons stays busy helping homeowners reclaim valuable backyard space.

Some takeaways:

* Explosion of ADUs is driving demolition needs. Nearly 1 in 10 hom...

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Royal Flush is the fastest growing portable sanitation company in the Vegas market. That wasn't always the case. When Scott acquired it, the trailing twelve months of revenue was only $150K. Now the business grosses over $3M. In this episode, we get a crash course in operating and growing a portable sanitation business.

Some takeaways:

* Most sanitation businesses are just “buying a job.” The majority...

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After a career in the Marine Corps, Dominick exited the service and joined Corporate America. A few years in, he came across Buy Then Build and set out to acquire a business. Fast forward a few years, and he's acquired two HVAC businesses in Southern California and has launched an AI consultancy focused on helping Main Street service businesses leverage Artificial Intelligence.

In this interview, we ...

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In 2019, Joe acquired Sonny+Ash, a 3D rendering firm based in Chicago. After weathering a pandemic and hiring a GM, he set his sights on a second acquisition. This time he looked for larger businesses with plans to raise equity to fund the deal. He closed on Point B Communications in 2024, buying 96% of the company using a combination of SBA debt, his own savings and investor capital.

In this interv...

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In 2022, Jeremy quit his career in corporate law to throw himself into the world of business ownership. He moved with his wife and kids to western Pennsylvania and set out to find a business to buy. The infrastructure bill had recently passed and so he shortly narrowed his focus to businesses in the underground infrastructure space. This led him to acquire Sewickley Construction Products, now known as Prime Contractor Supply.

In th...

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