Dylan Bowman is Still Figuring it Out — Borderlands Trail and Ultra Running

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?

[Long Live the Local Ultra | Nov 1 | Salt Lake City]

Presented by Kiprun.

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.

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Thumbnail photo: Ryan Thrower

If you’re new to Borderlands, start here.

Topics / Timestamps

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

Resources / Links

Related Episodes

Ultra Running isn't Just Running

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Borderlands explores trail running through culture, media, and the forces shaping it.

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