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.

• 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

• Freetrail
• Salt Lake Foothills Trail Races
• Josh Rosenthal on IG
• Borderlands.cc

• Ultra Running isn't Just Running

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

Watch on YouTube

Read on Substack

Ultrarunning gives ordinary people a rare place to feel strong, capable and tested. You don’t have to be elite, or even particularly good at it, to experience that. I know because I’ve DNF’d plenty of 100 milers, and when I finally finished Zion 100, I was the last guy across the line.

Watching The Rookie with my son made me realize why that feeling matters so much. As adults, most of us lose the arenas where we get to find out what we’re made of. Maybe ultrarunning is one of the last ones we have left.

Presented by Kiprun.

Please give us a follow, rate the podcast, and give a review.

If you’re new to Borderlands, start here.

• 00:00 You Don’t Have to Be Good at Ultrarunning
• 01:03 What The Rookie Made Me Realize
• 03:46 Adults Lose the Arena
• 06:16 Stepping Back Into the Arena
• 12:26 Finishing the Zion 100
• 16:31 The Dignity of Ultrarunning
• 20:17 Long Live the Local Ultra

• Salt Lake Foothills Trail Races
• Borderlands.cc

• Ultra Running isn't Just Running

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

Watch on YouTube

Read on Substack

Anton Krupicka has spent two decades becoming something harder to define than a trail runner. This conversation is about how that happened, why he stopped caring about fitting the sport’s mold, and what it looks like to keep evolving without chasing relevance.

We talk about the injury that changed his relationship with running, the move toward scrambling and climbing, his influence on trail culture, the Leadville comeback, and why La Sportiva still makes sense for the athlete he is now. More than anything, it’s Anton on identity, aging, design, and trying to stay the peak version of yourself without pretending you’re still who you were ten years ago.

Please give us a follow, rate the podcast, and give a review.

If you’re new to Borderlands, start here.

• 00:00 Anton Krupicka on why trends don't matter
• 01:30 From trail runner to mountain man
• 03:52 When the whole landscape opened up
• 08:24 Identity, trends, and trail running culture
• 16:45 The Leadville 100 comeback
• 21:12 The peak version of yourself

• Unbreakable | Western States Film
• Anton's 2021 Leadville Race
• Salt Lake Foothills Trail Races
• Borderlands.cc

• Ultra Running isn't Just Running

Presented by Kiprun.

----

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

• Watch on YouTube
• Read on Substack