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 whole arc, and the lessons that came with it. In this episode: The full PE transaction story: two years of due diligence, a deal falling apart on funding day, and the founder ultimately taking a bigger check the second time around The three year vision that got nearly finished in 18 months, and the new one aiming for $175M across 5-6 southern states, 17-20 locations, and 1,400-1,500 employees by 2029 Why labor hours (not labor dollars) is Roebuck's number one operational KPI, and how they use overtime as a retention tool instead of a red flag The Law of the Lid in practice: how Josh is delegating the operational side he has personally run for 30 years, and why "the strength of the CEO is the weakness of the company" The people-first framing that made a PE partnership work, and why "if they're not talking about their people in the first few minutes, it's not the right table" Josh's trade secret is simple. You are owed nothing. Show up every day like you have to earn it, bring value, and the outcomes will find you. That mindset carried him from 5th employee to CEO of a nine figure Southeast platform. If you are a founder thinking about an exit, a COO stepping up to the top seat, or an operator trying to build a vision your team can see themselves inside of, this one is a masterclass. JW Group Website: https://www.jwhitegroup.com/ Justin LinkedIn: https://www.linkedin.com/in/justin-white-%E2%98%85-35b7a210b/ Justin Instagram: https://www.instagram.com/justinwhiteceo/ Justins Youtube: https://www.youtube.com/@justinwhiteceo Roebuck Landscaping: https://www.roebucklandscaping.com/ K&D Website: https://kndlandscaping.com/ K&D Instagram: https://www.instagram.com/kanddlandscaping/ Disruptors Community: https://www.skool.com/disruptors Disruptors Advantage Newsletter: https://disruptors-advantage.beehiiv.com/