Episodes

  • The FKT That Took Bob Stewart 3 Tries to Finish
    Jun 5 2026

    Bob Stewart joins the Free Outside Podcast fresh off finally setting the Benton MacKaye Trail FKT after two previous failed attempts.


    What started as a backpacking challenge turned into an obsession with Fastest Known Times, leading Bob to records on trails like the Superior Hiking Trail, Pinhoti Trail, Mid State Trail, and now the Benton MacKaye Trail.


    In this episode we talk about why the Benton MacKaye became his "white whale," sleep deprivation, hallucinations, unsupported FKT strategy, bizarre trail encounters, cold-soaked backpacking meals, and what keeps bringing people back to these massive endurance projects.


    Bob also shares stories from the trail, including seeing great white sharks in the woods, imaginary hiking partners, and trying to explain a 289-mile FKT to confused campground hosts.


    Topics:


    -Benton MacKaye Trail FKT

    -Failed attempts and coming back stronger

    -Sleep deprivation and hallucinations

    -Unsupported FKT strategy

    -Superior Hiking Trail and Pinhoti Trail

    -Backpacking vs FKTs

    -Nutrition and gear

    -Why obsession can be a superpower


    Support our Sponsors:

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    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    1 hr and 7 mins
  • Rory Linkletter on the Olympics, Social Media, and the Future of Running
    Jun 1 2026

    Rory Linkletter is one of the best marathon runners in North America, an Olympian for Canada, and one of the most thoughtful voices in professional running.


    Fresh off a 2:09 performance at the Ottawa Marathon and a congratulatory call from the Prime Minister of Canada, Rory joins the Free Outside Podcast to talk about life as a professional marathoner.


    We discuss what it's like racing at the Olympic Games, how elite marathon contracts and appearance fees work, why the marathon may have surpassed track and field in popularity, the realities of building a personal brand as a professional athlete, and how social media has changed the sport.


    Rory also shares insights into his training, highest mileage weeks, recovery philosophy, strength work, marathon pacing, heart rate data, and the mindset that has helped him become one of the world's top marathoners.


    We also dive into trail running, Western States, sponsorships, podcasting, and whether a future switch from roads to trails could ever happen.


    Topics:

    • Ottawa Marathon recap

    • Call from the Prime Minister of Canada

    • Olympic Village stories

    • Marathon vs track and field

    • Pro running contracts and appearance fees

    • Building a brand as an athlete

    • Social media and sponsorships

    • Training 130+ mile weeks

    • Recovery, fueling, and consistency

    • Western States and trail running

    • The future of professional running


    Follow Rory:

    @rory_linkletter


    Support our Sponsors:

    Sawyer: https://sawyerdirect.net/

    Janji (code: Freeoutside): https://snp.link/a0bfb726

    CS Coffee: CSinstant.coffee

    Garage Grown Gear: https://snp.link/db1ba8ab


    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    1 hr and 27 mins
  • Sage Canaday on Competition, Content, and the Future of Running
    May 29 2026

    Sage Canaday has done a lot in running.


    A 2:16 marathoner, mountain running champion, Western States golden ticket winner, coach, YouTuber, and one of the few people who can jump into a conversation about track workouts, UTMB, 200 milers, social media, and sports nutrition without it feeling out of place.


    In this episode, we talk about Sage's "Any Surface. Any Distance." philosophy and how he went from chasing Olympic Trials standards to racing ultras and building one of the longest-running YouTube channels in endurance sports.


    We also dive into how running has changed over the last decade. The rise of influencers, AI coaching, optimization culture, sports nutrition trends, sponsorships, and the blurry line between being a professional athlete and a content creator.


    Along the way, Sage shares stories from Western States, his battle with a pulmonary embolism, losing his apartment in a fire, rebuilding his career, and why he still believes there are new challenges worth chasing at age 40.


    We cover:


    • Why 100 milers humble fast marathoners

    • Cocodona and the rise of 200-mile racing

    • Social media's impact on running culture

    • AI coaching and the future of training

    • Sports nutrition, bicarb, and optimization trends

    • Aging as an athlete

    • Clean sport and performance-enhancing drugs

    • Western States bear encounters

    • Why Sage still wants to keep trying new distances


    Support our Sponsors:

    Sawyer: https://sawyerdirect.net/

    Janji (code: Freeoutside): https://snp.link/a0bfb726

    CS Coffee: CSinstant.coffee

    Garage Grown Gear: https://snp.link/db1ba8ab


    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    1 hr and 9 mins
  • The Mental Side of Ultrarunning | Lauren Jones on Failure, Hallucinations, and Hard Things
    May 25 2026

    Lauren Jones.


    Lauren balances a demanding career as a pediatric nurse anesthetist, family life, and somehow still finds time to chase some of the hardest endurance goals imaginable. Multi-day races. Cocodona. Fixed time racing. Running over 150 miles in 24 hours. Team USA. Hallucinations. DNFs. Successes. Failures.


    We talk about balancing life with training, learning how to fail without letting it define you, why hard things can make other hard things easier, and how radical acceptance of failure can unlock growth.


    Lauren shares stories from Cocodona, fixed time racing, hallucinating deep into ultramarathons, running 154 miles in a day, and what keeps bringing her back to difficult challenges.


    We also talk about getting back into running after Cocodona, Memorial Day reflections, honoring sacrifice, and why maybe the point isn't perfection. Maybe the point is showing up anyway.


    Topics:

    • Cocodona 250

    • Fixed time racing and Desert Solstice

    • Running 154 miles in 24 hours

    • Team USA experience

    • DNFs and learning from failure

    • Hallucinations and sleep deprivation

    • Balancing career, family, and training

    • Mental strategies for ultrarunning

    • Why we keep choosing hard things


    Thanks to Janji, Garage Grown Gear, Northeast Trail Adventures, and Montana Meltdown for supporting the show.


    Support our Sponsors:

    Sawyer: https://sawyerdirect.net/

    Janji (code: Freeoutside): https://snp.link/a0bfb726

    CS Coffee: CSinstant.coffee

    Garage Grown Gear: https://snp.link/db1ba8ab


    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    52 mins
  • Why Trail Running Can't Stop Fighting Itself: TLDR Dumpster Fire Observations
    May 21 2026

    Trail TMZ is back.


    Host and award-winning correspondent Allison Mercer dive into one of the strangest weeks of trail running that we have seen in a while. From the Satisfy and Adidas backlash and influencer culture debates, to doping discussions around Cam Hanes, Sage Canaday and clean sport, plus the growing role of social media in shaping running culture.


    We also talk FKTs, Will Peterson's Appalachian Trail attempt, upcoming Pacific Crest Trail action, why controversy dominates attention online, and whether running is losing the things that made it special in the first place.


    Topics:

    • Satisfy backlash and brand culture

    • Influencer running and authenticity

    • Cam Hanes, Sage Canaday, and doping conversations

    • Why negativity dominates social media

    • FKT updates and upcoming attempts

    • Will Peterson's Appalachian Trail

    • The future of trail running culture


    Support our Sponsors:

    Janji (code: Freeoutside): https://snp.link/a0bfb726

    CS Coffee: CSinstant.coffee

    Garage Grown Gear: https://snp.link/db1ba8ab


    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    1 hr and 5 mins
  • 40TH PLACE IN THE WORLD, The Midwest McGrady of Running
    May 18 2026

    Patrick “Bubba The Midwest McGrady" Kavanagh joins the Free Outside Podcast after surviving Cocodona 250 with less than two hours of sleep, a lot of hallucinations, and peak Midwest politeness.


    We talk about passive aid station etiquette, the infamous Cocodona “fight,” hallucinating sepia-toned family photo albums in Sedona, the MBA basketball challenge at Mingus Mountain, why ultrarunning and pickup basketball are culturally identical, and whether Cocodona needs more wildlife, rivalries, and SlamBall.


    We also get into:


    Why Midwesterners make great ultrarunners

    How Cocodona completely changes your understanding of distance

    Racing horses in Arizona

    Why adult life desperately needs competition

    Why every ultrarunner eventually gives up athleticism for exercise

    AND

    A billion-dollar business idea involving upside down pizza


    One of the funniest episodes we’ve recorded.


    Support our Sponsors:

    Sawyer: https://sawyerdirect.net/

    Janji (code: Freeoutside): https://snp.link/a0bfb726

    CS Coffee: CSinstant.coffee

    Garage Grown Gear: https://snp.link/db1ba8ab


    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    1 hr and 5 mins
  • The Good Wolf with Yassine Diboun
    May 15 2026

    Yassine Diboun comes on to talk about imposter syndrome, ultra running, positivity, sobriety, community, and why none of us actually feel as confident as we pretend to.


    Yassine has been in the ultra running world for nearly 20 years, from the old-school blog era and handwritten race applications to modern 200 milers and social media comparison culture. We talk about how the sport has changed, why we still get nervous at races, and how you can be incredibly accomplished at one thing while still feeling like a beginner at another.


    We also dive into Yassine’s “good wolf vs bad wolf” mindset, how he practices positivity without pretending life is perfect, and why community might actually be the most important part of trail running.


    Along the way we cover:


    The early days of ultra running

    Cocodona 250 and Mammoth 200

    Heat training and race anxiety

    Hallucinations and sleep deprivation

    Why comparison steals joy

    Sobriety and endurance sports

    Kids, trail running, and staying playful

    Why hard things should still be fun

    The mental side of ultra running


    Support our Sponsors:

    Sawyer: https://sawyerdirect.net/

    Janji (code: Freeoutside): https://snp.link/a0bfb726

    CS Coffee: CSinstant.coffee

    Garage Grown Gear: https://snp.link/db1ba8ab


    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


    #Trailrunning #Runningnews #Outdoors #Outdooradventure

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    1 hr and 8 mins
  • Cocodona 250 Was Pure Chaos
    May 8 2026

    Allison Mercer and I recap the chaos of Cocodona 250. From a tracker glitch that placed Jeff in Africa in 1969, to GI issues, hallucinations, Mingus basketball, sleepless nights, and a fifth straight top 10 finish, this year’s race felt bigger, faster, and stranger than ever. They also dive into the intensity of the competition, the growth of the sport, the power of crew and pacers, and the heavier moments that reminded everyone just how serious these events can be.

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    1 hr and 6 mins