About this episode
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 Subscribe to Substack: http://freeoutside.substack.com Support this content on patreon: HTTP://patreon.com/freeoutside Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF Email me to buy a signed copy of my book, "Free Outside" at jeff@freeoutside.com Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside Website: www.Freeoutside.com Instagram: thefreeoutside facebook: www.facebook.com/freeoutside