Most operators jump into acquisitions chasing hyper-growth. They want the shiny hockey-stick curve, the 500% year-over-year story.
Matt, the owner of Winning Services, went the other direction.
He bought stability. A 75-year-old HVAC company in Pittsburgh with ~$2M in revenue, $400K EBITDA, and $700K in real estate baked into the deal.
On paper it was a 3.1× multiple, but the real prize was the phone that never stops ringing.
That stability let him retrade when revenue slipped, structure seller notes with earnouts, and keep the former owner on board to protect 85% of commercial relationships. Instead of gambling on a “two trucks and a dream” shop, he bought big enough to matter and safe enough to sleep at night.
Why You Buy Stability
Buying stability doesn’t mean you avoid growth. It means you choose a foundation that won’t collapse when the market shifts.
- You de-risk the downside with real assets like property.
- You inherit a reputation that keeps the board full.
- You retain key relationships by keeping the seller close.
- You put yourself in a position to scale with confidence instead of panic.
Matt’s deal shows that in home services, boring can be beautiful. A well-run $2M company in a city with no $50M player leaves plenty of room to grow, but without the existential risk of starting too small or buying hype.
Lessons for Operators
When you are evaluating a deal, ask yourself:
- Is this business big enough to be a platform, or just a job in disguise?
- Does the purchase price reflect real risk, especially if revenue shifts mid-process?
- Am I de-risking with assets and structure, or relying on blind faith?
The Primary Takeaway
Durable, community-rooted growth will always beat chasing hyper-growth.
Matt proved that the smarter play is not always buying the flashiest business. It’s buying the one that lets you win long term.
Here’s Matt’s entire story:
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