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

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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:

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GarageGrownGear.com

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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

I sit down with Peter Mortimer, the champion of the inaugural Arizona Monster 300-miler. Just hours after finishing, Pete was back at work—because ultrarunning is expensive and PTO is a myth. We talk about his strategy for managing sleep, how he trains for 200+ mile races, and what it’s like to hallucinate a jaguar that turns out to be an actual cow.

Follow Pete Mortimer on Instagram: https://www.instagram.com/pjmortimer/

We also dive into Pete’s “finish it once” race mentality, his plans to take on the Triple Crown of 200s, and his alter ego as a culinary legend known as Pete’s Meats, feeding hallucinating runners brisket on mountain summits. Plus, the ridiculous story of how we first met—at the Barkley Marathons, where Pete forgot his bib number and everything went sideways from there.

Support us by supporting our sponsors:

Janji: Janji.com

Garage Grown Gear: GarageGrownGear.com

CS Coffee: Csinstant.coffee

If you like stories of long-distance suffering, sleep deprivation, racing horses at Man Against Horse, and the sheer absurdity of ultra culture, this episode is for you.

Chapters

00:00 Introduction to the Arizona Monster

03:06 Experiencing the Arizona Trail

06:01 Race Strategy and Pacing

08:51 Training for the 300-Mile Challenge

12:03 Mental Challenges During the Race

15:02 Post-Race Reflections and Future Plans

24:41 The Barkley Marathons Experience

29:04 Cocadona Training and Connections

31:30 Pete's Meats and Community Engagement

36:11 Philosophy of Racing and Travel

38:57 Unique Racing Experiences: Man Against Horse

42:54 Eight More Miles Coaching Philosophy

Keywords

Arizona Monster, ultra running, endurance races, race strategy, training, mental challenges, Peter Mortimer, Jeff Garmire, 300-mile race, pacing, Barkley Marathons, Cocadona, ultra running, Pete's Meats, community, racing philosophy, Man Against Horse, coaching, endurance sports, running experiences

I’m recording live (well, semi-live) while running through mossy, Jurassic Park-like trails outside Portland. Just minutes in, I round a corner and meet a man with a blood-covered hand telling me someone stabbed his dog with a switchblade. So naturally... I kept running.

Support our sponsors, janji.com, garagegrowngear.com, and Csinstant.coffee

In this chaotic on-foot monologue, I dive into the Gorge Waterfalls 100K, which just happened to be the USA Trail Team selection race for the Mountain Ultra Trail World Championships. I talk through the carnage (the race kind), recap the course records smashed by Adam Peterman, Shea Aquilano, and others, and reflect on how trail running might be entering a new competitive era.

Then, I join up with Derek Lytle post-race to break it all down: the athletes, the coverage, the waterfalls, and the fact that every race we've filmed has somehow produced course records. Coincidence? Probably. But we’re claiming it anyway.

Also... there's a very old cat named Blackberry.

Chapters

00:00 A Run Through the Unexpected

03:03 Trail Running Championships and Team USA

05:50 Gorge Waterfalls Race Recap

09:01 Record-Breaking Performances

11:56 Looking Ahead: Future Races and Competitions

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

Keywords

trail running, Gorge Waterfalls, USA Trail Team, championships, record-breaking, running safety, outdoor adventures, race recap, competitive running, athlete insights

Today on the Free Outside Podcast, I talk with Connor “Jackrabbit” Chapdelaine, who’s attempting the Calendar Year Triple Crown—thru-hiking the Appalachian Trail, Pacific Crest Trail, and Continental Divide Trail all in a single year. We break down how the idea got planted during a hike on the AT, what it takes to train for 8,000 miles, and why he’s bringing a pillow, a stove, and maybe even a thermos.

Follow Connor/Jackrabbit online: https://www.instagram.com/JackrabbitHikes/

Connor shares his strategy for navigating snow in the Sierra, reroutes on the PCT, and fires on the CDT—plus his plan to survive town stops without spending his entire budget. We also get into ultralight gear hacks, and his favorite trail meals. Connor breaks down his food tier list (spoiler: mushroom Knorr = trail exile) and how his dad is helping run the back-end logistics with a label maker and full “dad command center.”

Support us by supporting our sponsors:

CS Coffee: https://www.csinstant.coffee/

Janji: https://janji.com/

Garage Grown Gear: https://www.garagegrowngear.com/

If you’ve ever been curious about the logistics, gear, food, and mindset needed to thru-hike the PCT, CDT, and AT in one year, this episode is packed with real insight and ridiculous stories—including tuna and peanut butter wraps, dry-scooped coffee, and a thru-hiker potluck that no one asked for.

Chapters

04:00 The Aspiration of the Calendar Year Triple Crown

10:30 Overcoming Obstacles in the Journey

13:51 Planning and Timing for Success

19:25 Budgeting for the Adventure

24:20 Family Support and Logistics

25:12 Training for High Mileage

31:29 Food Choices on the Trail

37:58 The Quirks of Trail Humor

38:51 Trail Food Favorites and Disasters

40:56 Resupply Strategies and Bargain Finds

41:59 The Art of Coffee on the Trail

43:46 The Triple Crown Experience

45:38 Friendships Formed on the Trail

47:59 The Emotional Connection to Hiking

50:04 Gear Essentials for Long Trails

56:14 The Importance of Comfort Items

59:34 Post-Hike Plans and Future Goals

01:05:15 Memorable Trail Names and Their 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

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 pro ultrarunner Alyssa Clark to talk about racing at the highest level, dealing with self-worth and performance, and why hallucinating pandas might be a sign you're doing something right.

Follow Alyssa online:

Substack: https://substack.com/@alyssaclark3

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

Alyssa just won the legendary Hurt 100 and holds the Supported FKT on the Pinhoti Trail, but her journey to the top has been anything but easy. We dive into her start in ultras (skipping the marathon entirely), the challenges of racing in Europe, the reality of going pro, and the game-changing impact of working with a mental coach.

We also get into the weeds on topics like hydration strategy, sleep deprivation, why pacers and crew can be tricky, and how Strava sometimes kills the vibe. Alyssa opens up about running 95 marathons in 95 days, starting her Substack "Theorizing in Motion," and building a life around motion—both literally and creatively.

Support our Sponsors:

CS Coffee: https://www.csinstant.coffee/

Garage Grown Gear: https://www.garagegrowngear.com/

Janji: https://janji.com/

Whether you're into 200 milers, mental performance, or just love hearing real talk from someone who’s been through the highs and lows of this sport, this one's packed with insight, humor, and straight-up honesty.

🎧 Available wherever you get your podcasts.

In this episode, I dive into the recent controversy surrounding the Arizona Monster trail race, where a failed live stream led to a very public clash between the race director and the live stream operator. I break down what happened, explore how social media amplified the drama, and share some thoughts on how these kinds of disputes can be handled more constructively. Along the way, I also talk about what I’ve been learning in my recent training camp and reflect on the importance of keeping conflict resolution behind the scenes whenever possible—for the good of the sport and the people involved.

Support our sponsors:

-www.janji.com

-www.garagegrowngear.com

-https://www.csinstant.coffee/

Sound Bites

"We sprain news, we don't break it."

"This is going to be a tricky subject."

"Stay elite, my friends."

Chapters

00:00 The Arizona Monster Controversy

04:37 Social Media Warfare in Trail Running

09:22 Escalation of the Dispute

11:43 Lessons Learned from the Drama

12:32 Upcoming Events and Personal Updates

Keywords

Arizona Monster, trail running, social media, live stream, controversy, public disputes, race director, live streaming, community, drama