In this episode of JackQuisitions, Jack sits down in Akron, Ohio with Matt, who just closed on his very first acquisition: a 75-year-old HVAC and refrigeration company outside Pittsburgh. Fresh off the Breaking $5 Million workshop, Matt walks through the whirlwind of his first six weeks as an owner—what it’s like to take on a $2M deal, why he valued stability over chasing top-line growth, and how he’s transitioning from a career in big tech and Amazon Web Services to running a boots-on-the-ground service business.

From sourcing the deal through a broker, to navigating retrades when revenue dipped, to managing seller relationships and earnouts, Matt shares the hard realities behind closing his first SBA-backed acquisition. He explains how he de-risked the deal with real estate, why he insists on fixed legal pricing next time, and why building something steady for his family and community matters more than chasing 500% growth curves.

💡 What You’ll Learn:
How to source and negotiate your first small business acquisition
Why stability and history can outweigh chasing the biggest revenue number
Creative ways to de-risk a deal through real estate and seller notes
Lessons in managing brokers, lawyers, and SBA lenders
Why leaving a W2 for business ownership is a bet on yourself
How to build a company that supports your family, team, and community

💼 Business Modification Group —
The go-to business brokers for trades companies. Whether you’re buying or selling HVAC, plumbing, or electrical businesses, we help you navigate valuations, find deals, and close successfully. Get a free valuation as a buyer or seller and join our exclusive distribution list for the best opportunities in the trades market.

👉 Get Your Free Valuation Here
For Sellers
For Buyers

📩 Jackquisitions Newsletter — Your favorite source for how to buy small businesses. Real insights, smart strategies, zero gurus.

🖊️ Sign up HERE

💼 Special Thanks to First Internet Bank!

Looking to buy or expand a business? First Internet Bank is a National Preferred SBA lender specializing in acquisitions for the skilled trades. Their SBA loan program offers up to 90% financing for business acquisitions, partner buyouts, and commercial real estate—plus optional lines of credit to fuel future growth. Unlike traditional lenders, they take a “how can we” approach, making deals happen for both first-time buyers and experienced operators.

👉 Special Offer: Mention Owned and Operated for a reduced good faith deposit and a complimentary deal review + buyside prequalification.
Connect with Alan Peterson from First Internet Bank here

🎙 Host: Jack Carr
🎙 Guest: Matt Wynne  — Winning Services, Pittsburgh PA

Send us a text

Jackquisitions Newsletter — Your favorite source for how to buy small businesses. Real insights, smart strategies, zero gurus.

🖊️ Sign up HERE for more insights

📢 Enjoyed the episode?
✅ Like, Comment & Subscribe for weekly insights on business acquisitions, deal flow, marketing, and growth strategies!

📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.