Justin returns to the podcast and discusses the challenges and lessons from acquiring three Apple-focused businesses since 2020 amid consolidation in the Apple consultant community and difficulty targeting Mac-using clients. He describes buying a small Iowa Apple consultancy with the seller kept on for business development, only to learn ownership doesn't equal sales skill and that ex-owners often clash as employees; the owner left after disputes, but clients were retained and served remotely. He then explains acquiring a Colorado Apple training company to build a B2C training channel, but it failed due to lack of focus, content upkeep, staff turnover, and the effort required to produce non-evergreen training. A larger Missouri consultancy/Apple authorised service provider acquisition brought clients and a strong team but also personality conflict and a payment-structure mistake that strained cash flow. Despite stress and missed pay-checks, Justin says the acquisitions ultimately improved finances, team quality, and growth, stressing the need for stronger financial position and deal-specific negotiation.
00:00 Welcome Back
01:15 M&A Episode Setup
02:06 Why Apple MSPs Consolidate
07:43 Three Acquisitions Overview
10:03 Deal One Iowa Lessons
12:02 Owner Clashes After Buyout
16:21 Deal Three Missouri Personality
18:25 Deal Two Training Misfire
27:37 Deal Structures Cash Flow Traps
32:50 Big Takeaways And Closing
Connect with Justin Esgar on LinkedIn by clicking here – https://www.linkedin.com/in/justinesgar/
Connect with Daniel Welling on LinkedIn by clicking here – https://www.linkedin.com/in/danielwelling/
Connect with Adam Morris on LinkedIn by clicking here – https://www.linkedin.com/in/adamcmorris/
Visit The MSP Finance Team website, simply click here –https://www.mspfinanceteam.com/
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