Meet Jason Cannon, Winter Garden Photographer

Jason Cannon of Cannonfire Photography

These days, we are all “photographers” thanks to these handy built-in cameras on our phones. Many professional photographers can take amazing photos with their fancy cameras. If you are going to hire a professional photographer at all, why choose Jason?

Jason has incredible gifts for connecting with people and establishing trust, more than anyone I’ve ever met. After being married to him for over 14 years now, my completely biased opinion is that his authentic rapport with his clients is the hallmark of his photography portfolio.

You can’t edit trust in Photoshop.

Even if the photo subject is a building, scenic landscape, or a set of wedding rings, Jason continues to focus on the client and the end result of how they will feel when they view these photos.

It all started with a waterproof camera

I recently sat down with Jason to discover more about his photography background. He shared, “My dad was a hobby photographer when I was growing up. He took really great pictures of us as a family, as well as scenics, and we put those photos on the walls in our home.

Then in high school I took a photography class and loved it. That’s when I got my first camera, a waterproof camera. It had a rubber, impact resistant case that made it indestructible for active boys. I took it everywhere, playing sports, surfing, band functions, church camp… it was attached to me all of high school.

Jason with his first camera at a high school event

And then I got to college and majored in journalism because I love writing and I also love photography. I ended up taking photojournalism and then photographing a lot of Gator sports for the school newspaper and for the media guides for the athletic association.”

Jason practically grew up on the water. So it was no surprise when he continued, “My first job out of college was with an active lifestyle magazine’s publishing group. My job was editing, writing, and photographing with a fishing magazine. It was only two years out of college before friends started coming to me already and asking me to take pictures of their kids, capture their wedding, etc. Then I shot my first wedding in 1998.”

Establishing the Cannon Family in Winter Garden

Downtown Winter Garden, 2018. Photo by Jason Cannon.

After calling Winter Garden home in 2016, Jason began to serve the community by joining the West Orange Chamber of Commerce and volunteering his time with the organization. He loves the West Orange area because, “Whether it’s a business, charity, family, church, or government, people look out for one another and care for one another.”

Jason Cannon and Kara Cannon, holding Cannonfire Photography’s “2019 Small Business of the Year” award from the West Orange Chamber of Commerce presented in January, 2020

On any given morning you can easily find Jason at his happiest place - the West Orange Trail. “When I am not working, I am spending time with my family. I also like running and being active and fit.” This is the ultimate understatement, as he has completed seven full IronMan triathlons. “I also enjoy community events, which is something I love about the West Orange community throughout the year.”

Jason with his son at a community race in October, 2023

Cannonfire Photography then and now

Jason founded Cannonfire Photography in 1996. He began with wedding and commercial photography segments, then expanded to include family portraits and high school seniors. 

Cannonfire Photography’s first business card, circa 1997

However, he’s not known as a “wedding photographer” or “family photographer” like many other professional photographers in the industry. “I’m a community photographer. I’m the photographer my community trusts, regardless of the segment,” Jason explained.

Clients in all segments routinely comment on his relational, natural, individualized/personalized, and fun style. He noted, “Even in a business context, we can have a light-hearted mood as we create high quality photos for branding and marketing.”

They express delight and surprise with how enjoyable the photography experience was with him. And they are excited to display photography wall art in their home, share photos with family, as well as post headshots on their LinkedIn and marketing materials.

Jason’s photography impact on clients

Reflecting on specific clients, “There are some clients who have literally grown up with me as their photographer. I just took photos of my client Elliot’s marriage proposal. I took photos of his preschool graduation, family photos, high school graduation photos, etc. He trusts me with every milestone of his life because I’ve become family to the families I’ve worked with.”

Elliot’s proposal to his now-fiancee, Kinsey in 2023

As for another client family, they have “several kids who are neurodivergent. Other photographers have tried to capture family photos, but this mom told me that I am the only one that made a great personal connection with all of the kids. This also brought out the best in their expressions in family pictures.”

Jason recently took engagement photos for a couple from St. Pete. The future bride had been one of his high school photography clients approximately 10 years ago. She told Jason she specifically chose him to be her wedding photographer because, “You are the photographer that I trust and the only one I am looking to hire.”

Jason with his family, 2023

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