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

I sit down with Doc, the voice behind Hiker Trash Radio—a podcast that’s interviewed over 450 adventurers from thru-hikers to Barkley Marathons legends. We dive deep into Doc’s wild behind-the-scenes experience covering the 2024 Barkley Marathons as a first-time invited media member. From nearly camping in the wrong forest to building trust at the Yellow Gate, he shares how he captured the stories of runners, crews, and chaos at one of the world’s most mysterious races.

Check out the Barkley Marathons Bonus Episodes: https://open.spotify.com/playlist/5KrLfLJn9Joy6PwwX3uEFR?si=88778974ca8d44f4

We talk about John Kelly’s fun run finish, the brutal new Ball Bearing Hill, and the unglamorous truth about nap-induced DNFs. Plus, we explore the evolution of Hiker Trash Radio, the art of giving trail names, and why Doc’s doctorate turned into a trail moniker.

Check out Hiker Trash Radio YouTube: ⁨@hikertrashradio⁩

Spotify: https://open.spotify.com/show/4gvi6HyY4wdQ7u8wWdSnkx?si=db514a5572e34e34

Instagram: https://www.instagram.com/hikertrashradio

Whether you love the Appalachian Trail, John Muir Trail, Continental Divide Trail, or just thrive on tales of ultrarunning pain and perseverance, this one’s got something for every dirtbag dreamer.

support our sponsors:

Janji.com

GarageGrownGear.com

Csinstant.coffee

Chapters

00:00 Introduction to the Barkley Marathons

02:48 Doc's Journey to Cover the Barkley

06:07 The Anticipation of Race Day

08:49 Interviews and Insights from Runners

11:53 The Race Begins: Expectations vs. Reality

15:01 The Challenges of the Barkley Course

17:58 The Atmosphere During the Race

20:57 Reflections on the Race Experience

24:04 The Aftermath: No Finishers This Year

30:57 The Final Moments of the Race

32:01 Reflections on Race Difficulty

33:30 Media Coverage and Content Creation

36:01 The Evolution of the Podcast

37:48 The Journey into Backpacking

46:00 Trail Names and Their Stories

51:01 The Magic of Thru-Hiking

55:16 Exploring Adventure Stories

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

I sit down with Tim and Renee—better known as Simply the ⁨@reneeandtim⁩ . These two have thru-hiked the Pacific Crest Trail (PCT) and Continental Divide Trail (CDT), set a Fastest Known Time (FKT), and built a massive online audience with their content on backpacking, ultrarunning, and dehydrated trail meals.

Follow the Thru Hikers on the internet

Instagram: https://www.instagram.com/thruhikers/

TikTok: https://www.tiktok.com/@thruhikers?

Website: https://thruhikers.co/

We talk about their full-time careers in plant genetics and engineering to outdoor influencers, the pressure of going viral on TikTok, and what it’s like filming content while hiking thousands of miles. Renee shares the story behind her self-supported Oregon FKT and how spreadsheets, heatwaves, and stubborn fire seasons played a role.

Check out The Barkley Bonus Episodes: https://open.spotify.com/playlist/5KrLfLJn9Joy6PwwX3uEFR?si=cb96d5bf10ca48f3

Support our sponsors Janji.com, Garagegrowngear.com and Csinstant.coffee

Plus, we dive into:

-The realities of turning hiking into a career

-Dehydrated food experiments gone wrong (bibimbap, we’re looking at you)

Trail name origins ("Blue Man" and "Sausage")

-How to prep for your first long-distance hike (spoiler: you don’t need to be an expert)

-Their book combining backpacking recipes and advice

-And why trail running has become their go-to between big hikes

This episode is perfect for aspiring thru-hikers, FKT nerds, trail chefs, and anyone wondering how to turn a love of the outdoors into a lifestyle.

Chapters

00:00 Adventuring with an Audience

03:06 Balancing Careers and Adventures

05:59 The Journey to FKTs

09:00 The Transition to Ultra Running

11:56 Navigating Social Media Growth

15:04 The Process of Writing a Book

34:51 The Journey of Publishing a Book

36:44 Wildlife Encounters and Adventure Stories

41:05 The Art of Dehydrating Food for Hiking

50:29 Preparing for a Thru-Hike Adventure

55:40 Trail Names and Their Stories

Subscribe to Substack: http://freeoutside.substack.com

Keywords

Thruhiking, Ultra Running, FKT, Adventure, Social Media, Content Creation, Hiking, Outdoor Activities, Balancing Work and Adventure, Recipe Book, hiking, adventure, wildlife encounters, thru-hiking, book publishing, dehydrating food, trail names, outdoor stories, FKT, hiking tips