In this episode of Jackquisitions, Jack sits down with Chris Barr—an aspiring business owner deep in the trenches of due diligence after signing an LOI to buy his dream company.

What follows is a transparent, tactical breakdown of the financial, legal, and operational hurdles Chris is facing. From recasting sketchy financials to prepping for a potential retrade, this episode strips away the romanticism of acquisition and lays bare the gritty work that goes into closing a deal.

If you're serious about buying a small business, this episode is your field guide.

⚡ What You’ll Learn

• What happens after you sign the LOI: Chris’s real-time playbook
  
  
• Navigating financial recasting and spotting red flags
  
  
• Legal and operational due diligence—what most acquirers overlook
  
  
• Why your deal team matters more than your deal size
  
  
• When retrading is necessary (and how to do it without killing trust)
  
  
• The biggest mindset shift Chris had during diligence
  
  
• How to stay optimistic when things get messy
  
  
  

Whether you’re a first-time buyer or a deal junkie, this episode will sharpen your edge and help you prep for the real work behind business acquisition.

💼 Shoutout to Appletree Business Services

HVAC and plumbing pros—ditch tax surprises and unresponsive accountants. Appletree handles your books, taxes, payroll, and acquisitions, and they know tools like ServiceTitan cold.

🎁 Get a free tax & financial review or 10% off a QOE report.

👉 Book a call at [appletreebusiness.com] — tell Patrick Jack sent you.

💼 Buying Businesses?
Jackquisitions is the must-read newsletter for operators, acquirers, and deal junkies. It’s packed with real acquisition breakdowns, seller red flags, and proven strategies from the trenches.

📬 Join and get smarter on small biz M&A every week.
👉 Subscribe at https://www.jackquisitions.com/

👤 Hosted by
Jack Carr – https://x.com/TheHVACJack

👤 Episode Guest
Chris Barr

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 for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

Buying a service business with the idea of passive income? In this episode of Jack Acquisitions, host Jack interviews Thomas Beebe, a financial advisor who stepped into ownership of his family’s HVAC company. What started as a hands-off investment quickly turned into a hands-on leadership journey.

From remote team management to turning around a messy acquisition, Thomas shares the tactical decisions, operational missteps, and growth strategies that shaped his perspective on what it really takes to own and run a trades business. This episode is packed with real-world insight—whether you're planning to buy, scale, or just survive in the world of home services.

⚡ What you’ll learn
Why Thomas initially underestimated the involvement required—and how he course-corrected
The operational systems needed for remote management (and where they fail)
How to set up accountability when you’re not on-site every day
Insights from a turnaround: A case study of a friend’s messy HVAC acquisition
The critical questions Thomas asks in due diligence after seeing both sides
When to diversify into adjacent verticals like plumbing—and when not to
How to build a business that’s both profitable and people-first

If you’re buying a local service business or building one to scale, this episode will challenge your assumptions and give you frameworks for sustainable growth—even when you’re managing from a distance.

💼 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 [https://alanfib.com/]

💼Buying businesses?

Jackquisitions is the must-read newsletter for operators, acquirers, and deal junkies. It’s packed with real acquisition breakdowns, seller red flags, and proven strategies from the trenches.
📬 Join and get smarter on small biz M&A every week.
👉 Subscribe at [jackquisitions.com]

[https://www.jackquisitions.com/]

👤 Hosted by:
Jack Carr
👤 Episode Guest
Thomas Beebe

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 for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.

Buying a small business? In this episode of Jackquisitions, we follow Chris Barr’s journey to acquiring a pressure washing company using smart financing—combining cash, earnouts, and trusted advisors. From submitting the LOI to executing deep-dive due diligence, Chris shares what it really takes to close a successful acquisition.

You’ll learn how to build the right team, evaluate financials and legal risks, and structure a deal that fits your vision. Whether you're just exploring acquisitions or in the weeds of a deal, this episode offers an insider’s look at getting a service business acquisition across the finish line.

⚡ What you’ll learn

• What Chris looked for in an ideal pressure washing business—and how he sourced it
• The creative structure behind his LOI and financing approach
• Why specialization matters: How Chris leveraged his real estate pros for M&A success
• The step-by-step due diligence checklist across financial, legal, and operational domains
• How to avoid major pitfalls in banking and legal negotiations
• The must-have advisors you need on speed dial when buying a business
• How to evaluate seller-provided info and spot red flags before it’s too late
  
  
  

If you’re buying a local service business or scaling your portfolio, this episode gives you a framework to approach acquisitions confidently—with the right strategy and team in place.

👤 Hosted by:

Jack Carr

👤Episode Guest:

Chris Barr

💼 Shoutout to Appletree Business Services

HVAC and plumbing pros—ditch tax surprises and unresponsive accountants. Appletree handles your books, taxes, payroll, and acquisitions, and they know tools like ServiceTitan cold.

🎁 Get a free tax & financial review or 10% off a QOE report.

👉 Book a call here — tell Patrick Jack sent you.

💼 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

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 for tracking. Episodes may feature paid sponsors, but all opinions are our own. Always do your own research before making business decisions.