Dylan Bowman is Still Figuring it Out

Dylan Bowman has spent much of his life in trail running, first as a professional athlete and now as the founder of Freetrail, one of the sport's most influential media platforms. But what happens when the thing you love becomes the thing you're responsible for building? And how do you know whether the sacrifices have been worth it?

Josh sits down with Dylan at San Francisco Running Company for a conversation about ambition, identity, and the complicated relationship between running and the business of running. They get into the personal and financial cost of building Freetrail, the pressure of becoming a prominent voice in the sport, the strange world of trail running memes, and where professional trail running might be headed. Somewhere in all of it is a guy who's accomplished a lot and is still figuring out what success looks like.

Presented by Kiprun bit.ly/kiprun_yt

00:00 — Cold Open: Was It Worth It?
02:20 — Dylan's Complicated Relationship With Running
10:23 — The Personal and Financial Cost of Freetrail
15:42 — Ambition, Competition, and the Inner Critic
23:41 — Building Freetrail Into an Institution
29:56 — Influence, Responsibility, and the Future of Trail Running
40:48 — The Future of Professional Trail Running
46:35 — Backyard Ultras, Barkley, and What Defines the Sport
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Borderlands explores trail running through culture, media, and the forces shaping it.

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