What does it really take to walk away from stability and start over? In this episode of Entrepreneurial Shades of Gray, Dani Dials and Chelsey Sayasane sit down with Matt Garner, founder of Garner Lawn and Construction. After nearly a decade in corporate leadership, overseeing multiple retail locations, Matt made the decision to step away and build something of his own.

He started with one truck, one cutting season, and a willingness to figure it out as he went. Today, his company has grown to more than 30 employees, multiple crews, and major contracts, including taking over maintenance at Spring Hill College. Matt shares what those early days really looked like, the challenges that come with scaling a service-based business, and the “gray areas” most people don’t see… from hiring and leadership to cash flow, growth, and risk.