Growing up in Montana, the wilderness was ours to explore. My sister Jenna and I spent our childhoods casting flies, wading through creeks, and scraping our knees far too many times to count. Nature was not just the backdrop of our lives— it was the center of our lives.
Our passion for adventure led us to pursue our dream jobs: Jenna worked in product marketing at Nike, and I stepped into the life of a fishing guide. Jenna thrived in her role, and I loved the sense of freedom guiding gave me.
But far from the days of wading in t-shirts and shorts, I worked in heavy, expensive clothing befitting a professional. I may have been on the water, but my shirt weighed on me like a suit. By the end of each day, my outfit stuck to me like plastic wrap.
During my summers guiding, I kept coming back to the same question: Why did I feel irritated and uncomfortable on the water? I knew there had to be a better solution, and it became my mission to create it.
I had a hunch I could make a better performance shirt with Jenna’s help, in part because we watched our parents run a t-shirt company growing up. After a brutal winter in the mountains, I packed up my car and drove to Charleston, lured by year-round fishing weather and a new base to work on Free Fly.
When I wasn’t on the water in the Lowcountry, I was researching fabric blends. After 18 months of testing materials, I came across an unlikely solution: Bamboo. Combined with a touch of quick-dry material, it became Free Fly’s secret sauce no one else had — sustainable, soft as butter, lightweight, odor-resistant, moisture-wicking, and UPF protective. Jenna and her husband Austin (who also worked at Nike) helped me transform the fabric into a simple performance shirt. The product felt like my time on the water: purposeful, uncomplicated, free to go with the flow.
I spent the next six months selling the Bamboo Lightweight Long Sleeve out of the back of my car at consumer fishing shows. I heard too many “no’s” to count, but I drove up and down the coast to shows and shops anyway. Despite my tired eyes and lingering doubt, we eventually started to get traction. By 2012, I had found a niche offering custom printing for specialty fly shops, partnering with 50 independent retailers and three sales reps. Collecting and incorporating customer feedback, we refined our original vision into a wider family of styles.
While Jenna and Austin were visiting Charleston on vacation the following year, I took them to our local spot, Hometeam BBQ, and pitched them a crazy idea: join me full-time as co-owners of Free Fly. After two stiff Gamechangers, they started to take me seriously. It was a lot to ask—to leave their well-earned spots on the corporate ladder in the rearview mirror.
But they took the risk and went all-in on a new family business, inspired by the sense of freedom and love of the outdoors that guided us as kids. In 2013, we squeezed the three of us, alongside Austin and Jenna’s English bulldog Arnold, into one tiny room of an office.
We kept hearing that our customers loved wearing our shirts everywhere (not just on the water), and we wanted the Free Fly community to include everyone who lived for the outdoors. Our next steps were clear: broaden our products to tops and bottoms while expanding our reach. For women’s products, we went against the industry trend of “shrink it and pink it.” Instead, Jenna took the helm to ensure that our women’s apparel was designed by women, for women in style and fit.
We continued to bootstrap our growth with a tiny budget and a lot of grit. Austin obsessed over every detail of product creation while Jenna tirelessly drove our e-commerce expansion and I continued to hit the road on long, grueling sales trips. We each had to find our balance as entrepreneurs who valued our freedom but also pushed ourselves to grow the business every day. Most of all, we had to put our egos aside, trust each other, and show up no matter what we faced.
We hit inevitable road bumps and made plenty of mistakes along the way. The three of us packed up orders on the weekends and included handwritten thank-you notes for each customer. We would sprint down the street to catch the UPS truck before the shipping cutoff. One time, a local printer sent us thousands of our brand-new shirts crumpled up in small balls. We spent two long days working in the local laundromat, throwing each shirt in the dryer for 10 minutes to de-wrinkle before folding them one by one. At that point, we had just doubled our retail partners and hired our first employees—and we were doing laundry as though our business depended on it. In retrospect, all of these moments were humorous but deeply humbling.
We learned from those growing pains, bringing our focus back to our vision. As we intentionally grew our product lines, we grew our team by picking people who matched our values from the get-go. Our team members are the backbone of our business, and they’re just as likely to be out on the water as they are to be serving customers in our downtown office. With each hire, Free Fly has become greater than the sum of its parts.
Almost ten years after this adventure started with a simple problem, we’re inspiring people to get outside and live life more comfortably. We still make mistakes, but we always stay true to our values and our humble roots. That’s why instead of partnering with big retailers, we work with 400 specialty stores and serve our community directly through our own e-commerce site.
So not much has changed, yet everything’s changed. We still go to Hometeam BBQ, now with our kids in tow. We keep it simple on and off the water, even as our product lines, team, and community continue to expand beyond our dreams. And nature is still at the center of our lives, so much so that we’re upping our conservation efforts to protect ecosystems and water sources for generations to come.
If you take the long view, it all looks pretty good. We can’t wait to see where the tide takes us from here.
Being from Arkansas, this heat and humidity is really oppressive in the summer. I love the lightweight and comfortable feel of all your products. I love them all especially the Hydro short. Nothing out there like it. Also the other shorts and shirts it’s almost like you have nothing on. Thanks so much for making an incredible product. I love them all, have I said that already?
I love your products! Comfortable and stylish, they have become my favorite to wear both on and off the water! Thank you for all that you do!
Whether it’s on the stream, an early AM workout, a Summertime BBQ or just simply lounging around the house, Free Fly is a brand and a line for all seasons and it’s quickly become one of my favorite clothing lines period. Keep doing your thing, Free Fly Team!
I love the story and I am also an past 16 year NIKE employee. I love your products especially the Nomad pants which I have one in each color and all shorts! Please come out with a 5 pocket pant quickly with a boot cut. Keep coming out with great products.
Saw your story on the Post and Courier site and you seems like an awesome company. Are you hiring or accepting resumes for software/web development positions?