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In 2019, Dylan Bowman received the kind of devastating news that no professional runner wants to hear: he had broken his left ankle.
By that point, he had been a professional trail runner for the better part of a decade, and this was easily the biggest setback of his career. “It was a super depressing moment,” he told me. “Up until that point I had been totally healthy throughout a decade plus of racing professionally. Even before that, when I was playing lacrosse in college, I never missed a practice, let alone a game, due to injury.”
Bowman had about a year of recovery ahead of him, and that reality forced him to meditate on how he could use this slowdown period to his advantage. “I was 33 years old and was really starting to feel the urgency of time and just the finite nature of being a professional athlete.” Back then, he didn’t have much of an online presence, but he’d long held a fascination with sports media, having grown up with subscriptions to outlets like Sports Illustrated and ESPN the Magazine. “I always felt in the back of my mind that I would love to have my own radio show or my own podcast or something.” As an avid listener of Bill Simmons and other sports podcasters, he was drawn to the audio format.
With his racing at a complete standstill, Bowman figured that then was as good a time as any to start podcasting. He scheduled interviews with several fellow professionals in the trail running community, and in late 2019 he launched The Well. “It was a homage to going to ‘the well,’ which is sort of a term of art in endurance sport.” The podcast found an audience almost immediately, and it soon dawned on him that it could serve as a launching pad for his post-racing career.
After all, trail running is one of the fastest-growing sports in the US, and Bowman was at the center of its tight-knit community. He felt that he had the credibility and the knowledge to build an enduring media brand that would serve this community. Around the same time that the podcast took off, he met Ryan Thrower, a professional photographer and videographer who expressed an interest in running the creative side of the business. “We had time on our hands,” said Bowman. “We had a lot of ambition. We had a lot of enthusiasm about this new project, and our skill sets were so different and complementary to each other that we just really hit the gas.”
In late 2020, the two co-founded Freetrail, a media outlet dedicated to the trail running community. What started as a single podcast soon diversified into written content, video, ecommerce, memberships, coaching, a podcast network, and even ownership of actual trail races. In a recent interview, Bowman explained to me how all these business models complement each other and why his company represents the next evolution in sports media.
Let’s jump into my findings…
Going pro in a fast-growing sport
Compared to most professional runners, Bowman entered the sport relatively late in life. He played a number of team sports while growing up and settled on lacrosse in college. It wasn’t until after graduation that he fell into running. “I was in a period of my life where I was a little bit lost,” he said. “My lacrosse career had come to a close at that point and I was looking for what was next.” He was living in Aspen at the time, and the mountains afforded him plenty of trails to run on. It didn’t take him long to begin signing up for races; he ran a marathon in 2009, and in 2010 he signed up for the Leadville 100, a famous ultra marathon that takes place in the Colorado Rockies. To his and everyone else’s surprise, he finished in third place.
The next year Bowman returned to the Leadville 100 and placed second, and then later that same year he achieved his first victory at the San Diego 100-Mile. By this point, he was absolutely hooked on the sport and was consistently training for upcoming races.
While there’s certainly plenty of cross over participation for both road races and trail races, the latter has its own distinct culture and training requirements. Not only does trail running involve a lot more hills and uneven terrain, it’s also commonly associated with ultra marathons. While most marathons take place in crowded, urban areas, trail running is a much more solitary sport, often requiring you to run alone in complete darkness, navigating hard-to-see trails with nothing but your headlamp to guide you. Needless to say, it takes a certain kind of rugged individual to enjoy such an environment, and trail runners pride themselves on their ability to endure harsh conditions.
Some ultra marathons award prize money to the winners, but they’re relatively paltry amounts. “The Ultra-Trail du Mont-Blanc, which is basically the default world championship for trail running, awards the winner with 10,000 euros,” Bowman explained. “The Ironman World Championship also took place in France, and the winner made $125,000, if I'm not mistaken. So you can see the difference in compensation just from a prize money perspective.” This means that, in order to go pro, trail runners need to find sponsors, and indeed Bowman started to attract sponsorships from brands like Red Bull and The North Face by the mid-2010s.
Luckily for Bowman, his entry into trail running came just as the sport was exploding in popularity, and so he was able to ride the wave of attention that sprung out of that popularity. But while many pro athletes have become adept at leveraging their fame to build an online audience, he never felt comfortable posting to social media. If it weren’t for his broken ankle in 2019, followed by the 2020 pandemic, he might never have found the impetus to launch any sort of media brand. With his career on pause and most races canceled, both he and his fellow pro athletes suddenly had a lot of free time on their hands, which made them all the more willing to come onto his newly-launched podcast.
The Well was a pretty standard one-on-one interview podcast. I asked Bowman why he thinks it took off so quickly. “The thing that I think made my show differentiated was I was really focused on the professional end of the sport,” he answered. “There were a few shows at the time that sort of touched that domain, but not from people who were as intimately involved in it as I was. My advantage was I knew all the athletes, I knew the dynamic, I've done all the races, and so I know what it takes to perform at a world class level. I also know the highs and lows that pros go through during the course of their careers, so I can empathize with them and we can talk about both the amazing things and the really hard stuff too.”
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