Meet Wesley Chiles

Chiles Enterprises was created as soon as I hit the age of 21, after a decade of experience in landscaping and gardening.

I was 10 years old there was a sweet old lady in our neighborhood that just moved there, she asked my mom if she knew anyone could mow her grass. So she said, “Wesley needs some exercise, why don’t you ask him to mow your grass…”

It was then that I started saving his money and bought my first lawn mower. I learned the instant gratification of when you show up and the yard looks kind of shabby, and then it looks nice and clean when you leave. It felt really good. 

When I was 14 my riding mower caught on fire (at a professional fireman house, nevertheless!), and that’s when I learned the value of insurance… and of course, safety. 

I took this really hard. I had just been published in the newspaper for all of my hard work in the community.

In the coming weeks, I got a call from a gentlemen who had a small engine repair shop. He helped me determine that it was a manufacturer error, so he gave me the money to replace it.

By the time I got my license I had two zero turn mowers and a tractor, and I was doing 70K in revenue by the time I graduated high school.

I did a two year degree at Virginia Tech in turf grass and landscape management, which is an amazing program.


I learned a ton from the business management program, which established the fundamentals of Chiles Enterprises. 

What started as a part-time neighborhood job, turned into a lifetime of caring for and mowing lawns.

Over time my part-time job grew into a full-time dedication to serving clients all over Louisa, Lake Anna and Charlottesville, VA.

If you would like to learn more about our company’s history, please watch the video below, in which Wesley explains his background and how he founded Chiles Enterprises.

Our Core Values

Quality People

Our awesome crew prides themselves on incorporating best industry practices and the newest technologies to produce top quality results for you.

Clear Communication

Your satisfaction drives our every action. Our goal is your peace of mind through clear and consistent communication.

Christ is our CEO

We are guided by prayer and personal relationship with Jesus Christ. We declare all our success in Him, and strive to honor Him in all of our work.
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