Starting and Scaling a Landscape Company — A Conversation with Trey Chilcoat

In this episode of the Kid Contractor Podcast, Brittany Auman sits down with Trey Chilcoat of From the Ground Up to explore the journey of starting a landscape design-build business during one of the most unpredictable times in recent history — the pandemic year of 2020.

Trey shares how he transitioned from working in commercial construction to taking a leap of faith and launching his own landscaping company full-time. From purchasing the company name in high school to managing large-scale apartment builds, Trey’s path wasn't linear, but it was deeply instructive.

He talks about the first-year challenges of equipment failures, financial sacrifice, and having to do any kind of work that came his way — from fences to grading — just to keep things moving. He also explains the shift from hiring friends to building a reliable crew of dedicated professionals.

A major theme of the episode is smart investment in equipment. Trey discusses the importance of mechanization, even at an early stage, and how buying a skid loader and a Mini-X helped transform weekend side gigs into efficient, profitable work.

For those thinking about scaling their own landscaping business, Trey’s insight into transitioning from field work to leadership — including a trial-and-error experience with hiring a salesperson — is particularly valuable. He reminds us that growth comes from calculated risks and a commitment to continual learning, especially in pricing, labor management, and systems.

Key Takeaways:

• Embrace the chaos of the early years and stay committed.

• Mechanization can be a game-changer for growth.

• Don’t underestimate the cost of inefficiencies — price accordingly.

• Leadership means learning from failure and adapting roles.