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.

  • How Ayden grew from mowing his own yard in 2022 to managing 90–100 weekly lawns with multiple crews
  • Why he’s keeping the focus on maintenance while slowly adding drainage work, small walls, and other project‑based services
  • The growing pains of running two crews without being on the truck yourself—and how better job notes and checklists help
  • How he estimates projects today using material takeoffs, target man‑hour rates, and lessons from underquoted jobs
  • Why employee reliability is a major constraint and what he’s considering (like seasonal visa workers) to solve it
  • How tight routing within St. Charles County keeps windshield time low while one “travel day” covers farther‑out customers
  • His vision for the next few years: two full mowing crews plus dedicated landscape and, eventually, hardscape and irrigation teams
  • Why most customers stay long term and naturally funnel more mulch and landscape work his way once they trust the mowing crew
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