#210 Trying to Buy a Business: Here’s What No One Tells You

 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 searchWhy opportunity cost is a real consideration in searchBehind-the-scenes of evaluating a pool service businessKey pros and cons of industry-specific acquisitionsHow Chris is using cold outreach and networking to source dealsThe tradeoffs between growth and early debt repaymentWhy no acquisition deal is ever perfect—and that’s okayRefreshing broker pipelines and learning from every interactionLessons 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.Connect with Alan Peterson from First Internet Bank here to get started Send Us Mail!More Ways To Connect with O&OJohn's Podcast YouTube ChannelOwned and Operated Newsletter Bonus Videos From JohnLeave a ReviewJohn Wilson, CEO of Wilson CompaniesJack Carr, CEO of Rapid HVAC📌 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.