ABOUT US | SHM

A Small Family Business Built Around Family

SideHustle Mowing is a small family-run lawn care business created by Gregory and Jessica James, are a devoted husband-and-wife team, as a way to stay active, and spend more time at home raising their children.

For Gregory and Jessica, family comes first. Everything they do is for their kids, and building a lifestyle that allows them to be present with their family has always been the priority.

A Career in the Creative Industry

For more than 30 years, Gregory and Jessica built careers in the creative and publishing industries. Together they founded and published their own magazines and worked with clients around the world.

Gregory James is an award-winning commercial photographer whose work has appeared internationally in advertising and editorial publications. Widely recognized within the industry for his fitness photography, he is considered by many to be among the top photographers in the world in that field.

Throughout his career Gregory photographed countless athletes, celebrities, and public figures, including talent from the NBA, NFL, television, and film. He also worked on productions involving major brands and film studios.

Within the fitness industry, Gregory served as chief photographer, creative director, and director of photography for 27 different publications, helping shape the visual identity of many magazines within the fitness and bodybuilding world.

Jessica James built her own reputation in the industry as a professional makeup artist, hair stylist, producer, and food stylist at the level of a chef. She worked alongside Gregory on countless productions and played a major role behind the scenes in bringing complex shoots together.

Jessica has always been the glue that holds everything together and the driving force behind it all, managing production and keeping their media company running smoothly.

A Change in Direction

After more than three decades in the industry, Gregory reached a point of physical and mental burnout. The constant travel, long productions, and pressure of commercial photography eventually took its toll.

With a growing family, Gregory and Jessica realized it was time to make a change and focus on building a life that allowed them to spend more time at home with their children.

Gregory stepped back from full-time photography and now only accepts select projects, typically about once a month.

Where SideHustle Mowing Began

While living in Florida, Gregory began spending time maintaining several large waterfront and estate-style properties in his neighborhood simply because he enjoyed doing it.

It was never a business at the time. He did the work strictly for fun and never charged anyone. Being outside, working with equipment, and taking care of property was something he genuinely loved.

Seeing how much Gregory enjoyed it, Jessica suggested turning the hobby into a small business.

That simple idea became SideHustle Mowing.

Life Between Florida and the Ozarks

Around the same time, the family made a lifestyle change. They sold their large home in Florida but still maintain a residence there.

Today the family divides their time between Florida and their farmhouse in the Ozark Mountains of Arkansas — typically spending winters in Florida and summers in the Ozarks.

SideHustle Mowing operates primarily during the warmer months while the family is in Arkansas. Gregory and Jessica intentionally keep the business small and seasonal.

Their goal was never to build a large company, but simply to run a small lawn care business they enjoy while staying close to home and raising their children.

The seasonal schedule also allows the family to take a few months each year to travel and spend time together.

Documenting the Journey

To keep his creative side active, Gregory began filming their journey.

The idea came from Jessica, who suggested documenting the process of starting the lawn care business on YouTube from the very beginning.

With Gregory’s background in photography and media production, filming and producing the channel came naturally.

The SideHustle Mowing YouTube channel documents everything — from buying and unboxing equipment to quoting jobs, working with clients, and learning the business along the way.

What started as a simple way to record the journey has begun gaining real traction. The channel has steadily grown and has even attracted a few sponsors — something Gregory never expected when he first started sharing the process.