In this episode we’re back with part two of the Chris Barr series on Jackquisitions. Chris is three months into his journey to acquire a business in Florida, and he’s bringing real updates from the trenches. From opportunity cost and deal dynamics to cold outreach and broker networks, this episode is packed with hard-won insights from an active business searcher.

We dive into the pros and cons of a pool service business he’s evaluating, the realities of navigating employee classification, and how acquisition imperfections are often just part of the game. Chris breaks down the lessons learned so far—from generating leads to refining search strategies—and why growth, not just debt repayment, should be the north star in any acquisition strategy.

If you're in the search phase or thinking about acquiring a service business, this is a front-row seat to the messy, insightful, and exciting reality of buying a company.

🔹 In This Episode, We Cover:

Navigating the first 90 days of a business search
Why opportunity cost is a real consideration in search
Behind-the-scenes of evaluating a pool service business
Key pros and cons of industry-specific acquisitions
How Chris is using cold outreach and networking to source deals
The tradeoffs between growth and early debt repayment
Why no acquisition deal is ever perfect—and that’s okay
Refreshing broker pipelines and learning from every interaction
Lessons in lead generation and seller conversations

🌐 More resources

👤 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 at Appletreebusiness.com — 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.

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John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC

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