Free Outside

In this episode, I sit down with Krista, winner of the Jeffrey Award for Most Tragic FKT, to talk about what might be the happiest tragic FKT of all time. We start with the infamous double Tahoe Rim Trail effort, an adventure that was never officially recognized, never really meant to be an FKT, and somehow still earned an award. From there, the conversation spirals in the best possible way. We ge...

Today on the Free Outside Podcast, I’m joined by Coleman Cragun, the winner of the Jeffrey Derrick Lytle Award, which is an honor with a proud tradition and a clear meaning (none of that is true). Coleman is an up and coming trail talent with the most relaxed confidence imaginable, and a nickname that may or may not stick: The Kraken. We get into Coleman’s origin story, including the moment he saw...

Comedic impressionist Dylisms is here. He has LOUDLY become one of the funniest voices in trail running by doing spot-on (and occasionally unhinged) impressions of the sport we all take way too seriously. We get into how he makes viral running videos using nothing but his phone, his car, and pure chaos, why he waited to run an ultra before posting running content, and how trail running compares to...

I’m back with Allison Mercer, my correspondent on everything, and we start with the most important news of the week: I apparently lost another award, and I am not interested in being reminded about 2025 when we are already deep into 2026. From there we get into World Cross Country Championships, which somehow had a full Florida theme including obstacle chaos, heat, and a crowd that sounded like 10...

At some point, a lot of us stop doing things just because they’re fun. We start asking if it’s productive, if it makes sense, or if it leads somewhere. And if it doesn’t, we quietly stop. In this episode, I talk about why I think that’s a mistake. From running winter laps on Main Street for Burrito League, to racing in Crocs, wearing a tiger hoodie, thru-hiking instead of getting a normal job, and...

The Free Outside Show is back for the new year, and I’m joined by our correspondent on everything, Allison Mercer. We’re doing the exact opposite of the usual “five months from now” preview content that other podcasts are doing, and instead talking about what’s actually happening this weekend: Bandera (with Molly Seidel), Houston Marathon for the OTQ watch, and why you should care about World Cros...

Endurance sports give me structure when life feels chaotic. Miles are measurable. Effort makes sense. Pain feels productive. For a while, that clarity can feel like purpose. In this episode, I zoom out on the uncomfortable truth that endurance sports have limits. The miles don’t fix self-worth, resolve identity, or heal everything we try to bury under training. I talk about what happens when the g...

I didn’t expect to win FKT of the Year for the Appalachian Trail, but here we are. This video is not about splits, miles per day, or how fast the record was. It’s about the decade-long path that led to it. From leaving college in 2011 and discovering thru-hiking, to years of chasing adventure while trying to fit into a traditional career, to hitting some of the lowest points of my life, including...

The conversation revolves around the Jeffrey Awards, celebrating achievements in ultra running, including new race directors, controversies, tragic FKTs, and the Walker of the Year award. The hosts discuss various nominees and their stories, highlighting the challenges and triumphs within the ultra running community. In this engaging conversation, Jeff Garmire and Derrick Lytle explore various the...

Jeff Colt is back, calling in from Carbondale with a mission to help rehabilitate the name “Jeff” one mountain town conversation at a time. We start with winter training reality in ski country, how to keep momentum when the days are short, the “subsistence” weeks that quietly save your season, and the eternal debate of pants, tights, and looking cool versus staying warm. From there it turns into a...

This week on the Free Outside Podcast, I am joined by Jeff Eklund, an “ordinary Jeff” calling in from North Carolina who quickly proves he is anything but ordinary. We kick things off with a Jeff quiz show where every answer is a different Jeff, and it immediately derails into the best kind of chaos. Jeff shares his winding path into running, including randomly ripping a 3:16 at Chicago in his 40s...

Vote on the Jeffrey Awards: https://forms.gle/zC29GEAgUJBKNn8T6 I brought the cowboy hat out for this one, because Month of Jeff needed full giddy up vibes. Jeff “Bronco Billy” Browning is back, and we go everywhere: Cocodona’s weird and wonderful rise into a spectator cult phenomenon, the tiny weather window that makes that race possible, and what it feels like when you are having one of those pe...

The Month of Jeff keeps rolling, and today we are giving the thru-hiking world some love. I tracked down a Jeff who just finished the Appalachian Trail in 2025, Jeff Coull, the guy behind the coullbean.com blog. Jeffreys Nomination Form: https://forms.gle/FiW9ZKNpiXoWb8MJ8 Follow Jeff on Instagram: https://www.instagram.com/coullbean/ Jeff wanted to hike the AT for almost a decade, but in 2024 it...

I sit down with yet another Jeff, but this one took things to a different level. Over the course of October and November, he completed 122 laps of the Manitou Incline, nearly a mile and over 2,000 feet of gain per lap, turning one of the most brutal stair climbs in the country into a month-long experiment in mental resilience. What started as training for a future unsupported FKT evolved into some...

It is Month of Jeff, so its time to talk to another Jeff, Jeff Pelletier. Jeff had a huge 2025. He paced and crewed at Cocodona, then took on Badwater 135 and followed it up with the inaugural Mammoth 200. We go deep on Badwater, why he was drawn to a race the core of the community has kind of fallen out of love with, and why he thinks it might be the hardest race in the world to crew. No aid stat...

Help us with our Jeffrey Award Winners by voting here: https://forms.gle/GAcHKf5QZrR7GAR79 The Month of Jeff continues with another elite Jeff: Jeff Dengate, better known on the internet as @dengatorade. Jeff is the director of product testing and de facto runner in chief at Runner’s World, and one of the most experienced shoe and gear testers in the world. He walks me through how Runner’s World a...

Vote for the Jeffrey Awards: https://forms.gle/2JaYdBFdogo2hTXP8 During the Month of Jeff I, sit down with a true Jeff of the Year contender, Jeff Mogavero. We cover a wild range of topics, from his fourth place curse at big races to winning Ultra Trail Cape Town, getting married, and somehow deciding Montana Cup might outrank all of it. Follow Jeff Mogavero: https://www.instagram.com/jeffmogavero...

I sit down with one of the true architects of modern running, Jeff Galloway. From making the 1972 Olympic team as an unexpected underdog to creating the RunWalkRun method used by millions of runners today, Jeff’s story is packed with history, perspective, and wisdom that still applies right now. We talk about the emotional crash that can come after achieving a massive goal, something I relate to d...

Get yourself a Crotch Pot: https://snp.link/cd93a18d In this solo Month of Jeff episode, I go deep on one of the strangest and coolest studies I have read in a while. It looks at capsaicin, the compound that makes hot peppers spicy, and how a small 12 milligram capsule taken before exercise can actually make you faster, more powerful, and more resistant to fatigue without raising heart rate or per...

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This is a Thanksgiving special episode of the Free Outside Podcast, a mix of long-run thoughts, unpopular opinions, and one of the most meaningful adventures of my life, the Great Western Loop. I talk about why I think we are historically illiterate, why it is okay to chase goals even if they feel pointless to other people, whether turkey trots have gotten too serious, and my very important theory...

I get back into the rhythm after my little sabbatical and dive into a packed rundown across the endurance world. I start with the history and results of the JFK 50, why JFK himself helped create 50 milers, and how the Kennedy Cup still defines the military competition at the race. Then I shift to the NCAA cross country championships and go deeper into what name, image, and likeness changes have do...

The P word. Purpose. After putting out more than 170 episodes in the past two years, I finally needed a break. The fall has been a rocky road, one of my favorite ice cream flavors, but also a tough stretch mentally. So I stepped back, went into the mountains, left the watch at home, and spent real time reconnecting with why I love moving through the outdoors. I talk about losing the sense of purpo...

This week on the Free Outside Show I pulled together a best of episode featuring some of the most memorable moments and conversations from the past year. These are the clips that stuck with me long after we hit stop on the recorder. You will hear Warren Doyle talk about the mindset he has carried through more than eighteen thru hikes of the Appalachian Trail. John Kelly talks about training for mu...

Do I fit in, in this industry? I have really started to question everything! I’m not doing great right now, and that’s what this episode is about. After finishing the Appalachian Trail FKT, there’s been a crash, the kind that comes after spending months focused on one goal. This episode is me reading and performing my Substack piece, Location Unknown, and trying to make sense of what comes next. P...