About Jonathan Orcutt

Founder and CEO of Driven Landscapes
Jonathan Orcutt, Founder & CEO of Driven Landscapes


  • Founder and CEO of Driven Landscapes
  • BS: West Virginia University Marketing and Business Administration
  • Founded Driven Landscapes at 28 years old.
  • Passed $1.2M annual revenue in just 5th year.
  • Other Interests:
    • Exercise.
    • Hiking with my dog (a chocolate lab), Charlie
    • Patriots football (screw you, Roger Goodell!)
    • Non-fiction reading, particularly business and entrepreneurial books.
    • Golfing with friends and business acquaintentces (even though I’m not that good).

Growing up, I was never a very big fan of school. Coincidentally, I had a lot of teachers who were never big fans of mine. School was boring and I rarely felt like they were teaching things that were going to be useful in my life.

But, for some reason, the thing I was a fan of was making deals and making money!

A Young Entrepreneur

In sixth grade, I started mowing lawns in the neighborhood using my family’s old 21-inch, 100-pound push-mower. I liked having spending money, but pushing that thing was brutal. And, oh yeah, it didn’t have a mulching feature, so emptying the bag was no fun either.

A short time later, I noticed that one of our neighbors had bought a new, light-weight, self-propelled mulching-mower. It was love at first sight!

I negotiated a deal with the neighbor where I would mow their lawn for free and, in exchange, I could use their magical mower to also do a half-dozen other lawns. A win-win. Not only was I making business deals, I was also learning about efficiency and the benefits of working smarter, not harder.

I continued my entrepreneurial efforts, running more than a dozen money-making “businesses” before graduating high school.

Trying some different things

I graduated West Virginia University with a degree in marketing and business administration.

Immediately after college, I spent a few years working for a couple different big companies, including Ryan Homes, a large, 15-state home-building company.

As a Project Manager for Ryan Homes I got first-hand exposure to the types of processes and systems a big company needs to succeed.

But the course had been set

After 16 years of schooling, I loved being out in “the real world” and I learned a ton from the big companies where I worked. But eventually the itch came back and I started thinking about starting my own business.

After doing so much landscaping work on my own over the years, it occurred to me that the landscaping industry is huge and full of opportunity, but without any dominant companies or brands.

I started Driven Landscapes with the idea of applying “big-business” systems, efficiency, and professionalism in an industry where those things are sometimes in short supply.

The first goal I set for Driven Landscapes was to grow to a million dollars in annual revenue. Four years later, I can check that one off.

The next goal: Expanding through franchising

People have been asking me why I’ve decided to expand through franchising rather than opening additional company owned locations.

To me, the answer is simple, though there are a couple parts to it.

Why franchise, part one

I want to work with people who are truly invested, both financially and emotionally. I’d far rather work with a dozen entrepreneurs who really care, than with bunches of employees with titles like “Regional Manager” and “Assistant to the Regional Manager.”

Why franchise, part two

I love mentoring people and talking about business. I love sharing ideas, giving and getting advice, and working together toward common goals. I want to be the resource that I wished I had when I first started my business.

I know there is more than enough work out there for everyone, and I don’t feel a need to try to keep every dime for myself. If I can watch my company grow and, at the same time, help like-minded people take control of their lives, I can’t think of anything that would make me happier, professionally.

Whether you are ready to start a landscaping business, ready to make changes to your current business, or just starting to explore your options, I'd love to talk with you. Feel free to contact me through the link below!

Jonathan Orcutt

Questions or comments?

Contact Me Here