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Josh McMillan: The 30 Year Climb From Employee #5 to Nine Figure Landscape CEO

This week on Trades Talk, Justin White sits down with Josh McMillan, CEO of Roebuck Landscaping out of upstate South Carolina. Josh joined the company as employee number five back in 1995, worked his way up to COO, survived a two year private equity due diligence process (including a deal that fell apart on funding day), and stepped into the CEO seat in December 2024.

Since closing, Roebuck has built its first ever company budget, drafted a three year vision, acquired The Great House Company in Nashville, and is running 12 to 15 percent organic growth on top of it. Josh walks through the…

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