Scaling from High School Hustle to a Two‑Crew Lawn Business

In this episode of The Landscaper Grow Show, host Mark Lamberth talks with Ayden Sullivan of Diamond Lawn Care in Wentzville, Missouri about how he grew a teenage side hustle into a multi‑crew maintenance company serving 90–100 lawns a week plus steady landscape projects.

Ayden shares how he went from mowing his family’s yard in high school to running two trucks, several trailers, three full‑time employees, and a part‑timer, with services that now include weekly mowing, fertilization, spring cleanups, mulch, bush trimming, drainage work, and small retaining walls.

He opens up about the real challenges of scaling off the mower—like giving crews clear written instructions, making sure the right tools are on each truck, and dealing with employees who don’t always show up—and how he’s learning to price projects by tracking man‑hours, materials, and overhead after underbidding jobs early on.

You’ll also hear his plans to add more maintenance routes and eventually dedicated landscape and hardscape crews, and why compact routes in St. Charles County plus strong relationships and five‑star service keep customers coming back for every new project.

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