How Dylan Bowman built Freetrail, a media outlet for trail runners

The Business of Content

For most of his career as professional ultra marathoner, Dylan Bowman didn’t have much of an online presence, but in 2019, he suddenly found himself with a lot of time on his hands after he broke his left ankle and had to take a year off from racing. That year, he launched a podcast where he interviewed his fellow pro runners, and it pretty quickly became a huge hit.

It didn’t take long for Bowman to realize that the podcast provided a huge opportunity for his post-racing career, so in late 2020 he and a co-founder launched Free Trail, a media outlet that operates a podcast network, a YouTube channel, and even its own ultramarathon races.

In an interview, Dylan walked me through how he built the company, his monetization strategy, and why it represents the future of sports media.