On today's episode of the Free Outside Podcast, I’m joined by outdoor filmmaker Drew Darby, and we cover everything from his unexpected start filming inside prisons to becoming one of the most exciting filmmakers in ultrarunning. We dive into how working in sensitive environments shaped his storytelling, the chaos (and comedy) of filming 100-mile races, and why long-form content is making a comeback. Drew shares his thoughts on building a career in the outdoor film industry, what it’s like to turn passion into a full-time job, and the importance of telling deeper stories beyond the race results. Plus, we brainstorm a "Media Mile" race, swapping cameras instead of trophies. It's an episode packed with filmmaking mishaps, creative advice, and a whole lot of laughs.

Follow Drew Darby online: https://www.instagram.com/drewbdarby

Chapters

00:00 From Prisons to Filmmaking: Drew's Unique Journey

04:35 The Intersection of Politics and Filmmaking

09:06 Short Form vs Long Form: The Filmmaker's Dilemma

17:27 The Pressure of Timely Storytelling

21:53 Navigating Brand Relationships in Filmmaking

28:58 Transitioning to Ultra Sports Filmmaking

38:35 Overcoming Physical Limitations

39:30 Transitioning to Freelance Filmmaking

42:12 Navigating Brand Collaborations

44:09 Life Beyond Filmmaking

47:18 The Challenges of Travel

49:26 Filmmaker Nightmare Stories

53:39 Advice for Aspiring Filmmakers

01:01:25 The Importance of Storytelling in Filmmaking

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Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside

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