EP136 – How I F'd Up Three Acquisitions: Lessons From Apple MSP M&A with Justin Esgar

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 – <span style= "font-siz