In this episode of JackQuisitions, Jack catches up with Chris Barr, who returns with a hard but valuable update: his most recent deal is officially dead. After months of diligence, capital invested, and a strong connection with the sellers, Chris made the tough call to walk away when the risk profile jumped too high. What could have been a dream business became a cautionary tale about what happens when books don’t line up, multiples stop making sense, and the juice just isn’t worth the squeeze.

Chris shares the emotional side of killing a deal, why it sometimes feels like “paying tuition” in the acquisitions school of hard knocks, and the critical lessons he’ll carry into his next LOI. From working capital debates to due diligence missteps, this conversation is a masterclass in knowing when to say no—without losing sight of the bigger goal.

💼 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: [https://businessmodificationgroup.com/jq/]
For Buyers: [https://businessmodificationgroup.com/listings/?statuses=ACTIVE]

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

🖊️ Sign up HERE for more insights

💼 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 to get started

🎙 Host: Jack Carr — https://x.com/thehvacjack
🎙 Guest: Chris Barr

📈 Keywords: small business acquisitions, dead deals, due diligence, working capital, risk mitigation, sunk cost lessons, acquisition strategy, ETA, service business growth

📌 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 o

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.

In this episode of JackQuisitions, Jack sits down with Jeff Bates, a Michigan-based operator who went from running trucks in the heat to owning and growing multiple HVAC companies. After years at Lennox and a crash course in small business while working for his father-in-law’s trucking company, Jeff and his partner decided to jump into ownership themselves.

Their first deal came in 2022 with RNL Heating & Cooling, a legacy business with real estate included. But the story didn’t stop there—just a year later, they acquired Hurside Heating & Cooling through a broker connection. Along the way, Jeff shares the reality of SBA financing, why branding and location matter more than you think, and how “Day One calls” convinced him to buy vs. build.

From navigating tuck-ins to learning the power of the supply house counter as the ultimate networking hub, Jeff walks through what it really takes to expand through acquisition while keeping culture strong.

💡 What You’ll Learn:

• Why Jeff chose buying over building—and the immediate payoff of legacy customers
• How to use supply houses and parts counters as a secret due diligence tool
• The tradeoffs of including real estate in an SBA-financed acquisition
• Branding pitfalls: when a company name works against you
• The importance of a no-asshole policy in preserving culture
• Why tuck-ins remain the best strategy for consistent HVAC growth

💼 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 for more insights

💼 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 to get started

🎙 Host: Jack Carr
🎙 Guest: Jeff Bates

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.

In this episode of JackQuisitions, Jack sits down with Matthew Railla, a former wine industry operator turned termite company owner. After years running his family’s winery, Matt discovered business brokerage through his brother-in-law—and eventually listed a highly profitable termite inspection company. When buyers kept passing due to its relationship-driven, project-based model, Matt had a realization: What if I bought it myself?

From that October 2023 “aha” moment to closing in June 2024, Matt navigated creative SBA financing, licensing requirements, and a stubborn seller’s attorney to acquire Top Termite. Now, he’s growing the business, expanding service areas, and exploring new B2B offerings—all while sharing lessons for first-time buyers.

💡 What You’ll Learn:

• How an industry outsider found and bought a business through brokerage work
• Why some profitable companies still struggle to find the right buyer\
• How to structure a partial buyout with only 5% down (under 2024 SBA rules)
• The role of trust, relationships, and reputation in non-recurring revenue trades
• Key team members every first-time buyer should have on their side
• The mindset shift from “doing it all yourself” to leaning on experts
  
  🎙 Host: Jack Carr — [https://x.com/thehvacjack]
  🎙 Guest: Matthew Railla — matt@toptermiteco.com | LinkedIn: Matthew Railla

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

🖊️ Sign up HERE for more insights

💼 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.
💼 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

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.