Dylan Bowman discusses building Freetrail, the personal and financial costs of running a media company, and his commitment to defining sustainable trail running culture.
Dylan Bowman makes it look easy. But beneath the enthusiasm is a real tension around building not only a good company that represents the sport, but the right company.
He seems to know that he’s standing on something we all believe to be sacred in a sport that feels inevitable and indispensable.
But believing in the importance of the thing doesn’t make the business of it any easier.
What struck me was his description of a deep “knowing” that this is the right thing to do, even as he wrestles with the fatigue, financial realities, and occasional resentment of building Freetrail.
There’s a difference between knowing what deserves to exist and knowing how to make it sustainable. Dylan seems remarkably clear on the former, even while working through the latter.
Presented by Kiprun https://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.
If you’re new here, start here: https://www.borderlands.cc/start-here/
Read on Substack (https://borderlandstrailrunning.subst…)
Listen on any podcast platform (https://pod.link/1725734721)
