Welcome! I'm Simon Owens and this is my media industry newsletter. If you've received it, then you either subscribed or someone forwarded it to you.

If you fit into the latter camp and want to subscribe, then you can click on this handy little button:

Sign up here

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.”  

Expanding into new content verticals

At first, it didn’t occur to Bowman that the podcast could become a real business; in fact, he was vehemently against monetizing it in the early days. “It wasn't until later that I really embraced the idea of, hey, this could actually be bigger than me and it could be something that really delivered a service to the community and the culture that had given so much to me.” Ryan Thrower, the freelance photographer who eventually became his business partner, helped him realize that the podcast could serve as an anchor for a larger media brand that operated across several mediums and business models.

That’s not to say that they landed on the correct formula right out of the gate. The first product they launched outside of the podcast was a subscription app that would help aspiring trail runners in their training. “Almost immediately, it didn't feel right,” said Bowman. Building and marketing a software product required a unique set of skills that neither of them had. “But it made us realize that there's a community of people who would pay us to just be part of the energy and the passion that we were bringing into this sport. So fast forwarding another year and a half, we ended up folding the app and sort of reimagining our subscription product underneath the greater understanding that we're a media company.”

By this point, they had rebranded this company to Freetrail, and over the next two years they began to roll out more and more content verticals underneath that brand.

For starters, Freetrail has taken the success of its anchor podcast and leveraged it to build a larger podcast network. It partnered with three female pro runners — Keely Henninger, Corrine Malcolm, and Hillary Allen — to launch a show called Trail Society. “They also happen to all have postgraduate scientific degrees,” said Bowman. “So their show is very much focused on training science.” A recent episode, for instance, focused on the research behind menstrual cycles and how it affects runner training.    

With the help of Thrower, the company has expanded its video offerings. Not only does it produce video versions of its podcasts, but it also publishes highly-produced mini documentaries about the sport. In October, for example, it posted a 7-minute video about the training regimen of a pro runner named Heather Jackson. The entire piece was shot on location in Phoenix, Arizona, which is where Jackson lives. To date, Freetrail’s YouTube channel has grown to 17,000 subscribers and 1.6 million total views. 

Freetrail began building out the written content on its website, mostly by relying on a network of freelance writers. It publishes first-person essays — like this one from an amateur runner about what it’s like to feel competitive even when you’re not a professional athlete — as well as reviews of running gear. Earlier this month, for example, it published a detailed review of a trail running shoe from a freelance contributor named Cody Jett. It also produces evergreen instructional content, like this article explaining when’s the best time to use poles in trail runs.

Building out multiple revenue streams

From a business model perspective, Freetrail is one of the most diversified media companies I’ve ever come across. Let’s run through its revenue streams:

• Memberships: Probably its most reliable revenue generator is its membership program. “It’s the thing we're most proud of and it brings us the most satisfaction,” said Bowman. “Instead of taking podcasts and articles and putting them behind a paywall, we mostly have 100% of our content public facing and free to the audience.” The main perk for members — other than supporting the brand and the mission of Freetrail — is access to a deep archive of training plans that are optimized for different levels of athletes. The membership costs $100 a year, and Bowman said they’ve grown it to about 1,000 members. 

• Sponsorships: It also works with several brand sponsors, most of which are featured on Bowman’s main podcast. The typical brand partner is a fitness nutrition or apparel company. 

• Coaching: Freetrail has built out a network of professional running coaches, and it engages in a commission-based lead gen where it pairs athletes with these coaches. “In addition to offering one-on-one traditional coaching, we also have very well-educated, well-credentialed people from the nutrition realm, from strength and physical therapy development, and from the mental health and mental performance side of things too,” said Bowman. “So we've really approached things holistically.”

• Races: Freetrail actually owns and operates its own trail races. “We have two races, one of which we've acquired and one that we started from scratch,” said Bowman. “The one that we acquired is just outside of Portland, Oregon. It's called Gorge Waterfalls. The one that we started from scratch will be here in my backyard in Marin County, California starting in February of 2024.” Freetrail monetizes these races through a mixture of entry fees and sponsorships.  

• Merch/product collabs/ecommerce: Freetrail has a standard merch store with branded items like socks and t-shirts, but it’s also teamed up with established companies to launch co-branded products. “We released a shoe with our footwear partner Speedland that has our Freetrail logo on it,” explained Bowman. “Just this week we released a drink mix with our nutrition partner, Gnarly Nutrition. In the Spring of next year, we're going to be releasing a capsule of trail running apparel with Goldwin, a Japanese apparel brand.” And as I mentioned above, it’s producing product review content that’s monetized with affiliate links. “We've barely scratched the surface of the affiliate world. I'm really enamored with the brands like MeatEater and Food52 and Hodinkee, and I think over time we've proven our credibility in the space and that we move product for our partners.”

In many ways, Freetrail doesn’t act like a traditional media company, and I posited to Bowman that this is because it’s an outgrowth of his already-existing career as a pro athlete. “I agree one hundred percent,” he replied. “I think this is a macro trend that is only going to accelerate.” He pointed to other creator-led brands like Prime — an athletic drink co-founded by YouTubers Logan Paul and KSI — and MrBeast’s Feastables as a model he’s trying to emulate. “I'm trying to hopefully thread the needle where I can be an individual creator with my own personality but also build a larger brand that launches its own products. I think that really is the wave of the future.”

Growing responsibly

Prior to launching Freetrail, Bowman’s main focus was maintaining his athletic performance so he could win races. I asked him if he still had time to train given that he was now running an entire media company. “Man, it is nuked,” he said, laughing. “It totally ruined my athletic career. Last week we were at the [Ultra-Trail du Mont-Blanc] in France. We were doing a full week of content. We had a daily show every morning. We did a lot of pre and post-race interviews with the pro athletes, and it was a huge success for us as a company, but for like two hours every day I was just consumed with sadness that I've just sort of sacrificed my entire athletic career in order to pursue this.” That’s not to say he has any regrets. “I love this business, I love this industry. I'm 37, so long term, this is the future for me.”

The company is completely bootstrapped, and his team is mostly made up of contractors. In our interview, Bowman acknowledged that he’s feeling a little overwhelmed by the number of plates he has spinning in the air. “The business has sprawled to where everybody who works on Freetrail is kind of at their max capacity,” he said. “And so now it's just a matter of being disciplined, slowing down, and not losing focus on those core elements. We have been sprinting nonstop and have so many different verticals. We have so many different pieces of IP at this point that it's really about figuring out how do we really refine and execute each of these pieces of IP, and how do we maximize them from a monetization and an operational standpoint?”

That’s not to say he’s given up completely on his athletic career. “As a 37-year-old, I’m chasing this media business with the same energy, the same enthusiasm, the same level of discipline that I chased my own athletic career, but I do hope that I'll still have a couple of cycles left where I can buckle down and focus and really train and race, hopefully at a world class level again.” 

I need your help

Articles like the one you just read take me weeks to research and write. I’m almost entirely reliant on paid support from my audience to fund this type of work.

If you feel these articles provide value, please consider becoming a paid subscriber. Subscribing gets you an introductory call with me and full access to my archive of case studies.

Use the link below and you’ll get 10% off for your first year:

Get 10% off for 1 year