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Buying and Scaling a Towing Business
Matt Saskin from East Coast Towing talks towing, tech, and more
John Wilson
April 16, 2025
What’s up everyone,
I’ve got a good one for you today.
In yesterday’s podcast, Jack went solo and sat down with Matt Saskin from East Coast Towing. Mad I missed it, but it was a cool conversation.
They talked about Matt’s history in tech, his move into the towing industry, and how to break into this space.
Reminder: Our new podcast series, JackQuisitions, is launching May 2nd. I can’t explain how excited I am about this. Help me out with this survey one last time…
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Buy a Towing Company, Then Scale It
Is it worth buying a towing company?
It’s a common question.
After listening to the latest O&O podcast episode with Matthew Saskin, a tech exec turned towing operator, here’s the answer: Sometimes.
But tread carefully — especially in a fragmented market full of overpriced trucks and vague financials.
Most towing businesses are just trucks and vibes
Matthew bought his first towing company in Raleigh after selling a real estate portfolio post-COVID. He wasn’t chasing shiny vehicles. He wanted cash flow, operational maturity, and a business he could scale.
He found one — but it took work.
He passed on the “flashy” trade shows with chrome bumpers and vendors pitching to hobbyists. Instead, he went deep on a smaller summit where real operators were talking business strategy and margins.
The business he bought had already survived an ownership transition. The widow of the founder was running it with her father-in-law. Neither drove trucks. It wasn’t reliant on one person. That alone made it rare.
He liked that the team already operated independently. No need to be in the cab. No need to answer dispatch calls at 3am.
What makes a towing deal worth skipping?
Here’s what Matthew sees all the time:
Too many trucks, not enough revenue
Owners overvaluing assets, underestimating overhead
24 trucks but 25 employees = no scale, no structure
SDE instead of EBITDA = unclear margins
Asking 5x+ on a business barely clearing $400K
Matthew reviewed one listing asking $2.4M on $2.8M revenue and just $400K cash flow.
“Most of these businesses are worth their asset value—maybe,” he said. “But they want that plus a premium.”
The model works — if the business runs without you
The model can scale. Matthew’s living proof of that. He’s expanded to six locations, added adjacent verticals (like heavy hauling and fleet maintenance), and built a real org chart with promoted managers.
But he waited until his team was solving problems the right way—not just the fastest way—before making his next move.
The question to ask before you buy
If you're looking to buy a towing business (or any service business), ask yourself this one very important question:
Is this a real business, or just a guy with too many trucks?
Because in this industry, there’s a big difference.
More on buying and scaling towing companies here ⬇️
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That’s all for today, but I’ll be back on Friday with another newsletter. I’ve got some ideas cooking, so you’ll want to stop back.
Cya,
John
Disclosure: This newsletter includes sponsored content. However, all opinions expressed are entirely my own.
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