Building the Event Trail Running Has Been Missing

Building the Event Trail Running Has Been Missing

Trail running is growing faster than anyone predicted. New brands are entering the space, race fields are selling out, course records are falling, and the sport is attracting capital, media attention, and mainstream audiences it has never seen before. But growth without infrastructure creates problems. Who is having the hard conversations? Where does the industry get together to figure out where it's going? That is the problem Dylan Bowman and Doug Emslie set out to solve with TrailCon. Now heading into its second full edition in Palisades, California, the event has become the closest thing trail running has to an annual gathering of everyone who makes the sport what it is, from elite athletes and race directors to emerging brand founders, media people, and the runners who show up every weekend just because they love it. Dylan and Doug join Long Run Labs to talk about why TrailCon exists, what it takes to build something durable in a sport that is still figuring itself out, and why face-to-face community has never mattered more. Jon, Dylan, and Doug chat about: * the origin story of how Dylan, Doug, and Brendan Madigan came together to build it * what separates events that last from events that fizzle out * the Trail Running Hall of Fame and why honoring the past matters as the sport professionalizes * the emerging brand zone and why entrepreneurial energy in the sport deserves a platform * how On became the title sponsor before TrailCon was even a real event * the tension between free admission and building a sustainable business model * protecting public lands and the partnership with Runners for Public Land * what intentional serendipity actually looks like and why it drives real business outcomes * the Second Nature meetup and turning a digital community into a physical one Stay connected: TrailCon website: https://trailconference.com [https://trailconference.com] Second Nature Podcast: https://podcasts.apple.com/us/podcast/second-nature/id1737242598 [https://podcasts.apple.com/us/podcast/second-nature/id1737242598] Doug on LinkedIn: https://uk.linkedin.com/in/douglas-emslie-2540405 [https://uk.linkedin.com/in/douglas-emslie-2540405] Dylan on LinkedIn: https://www.linkedin.com/in/dylan-bowman-06174380/ [https://www.linkedin.com/in/dylan-bowman-06174380/] Dyland on Instagram: https://www.instagram.com/dylanbo/ [https://www.instagram.com/dylanbo/] This episode is supported by: Popfly: If you're a brand trying to reach outdoor, travel, and adventure audiences, Popfly is where to do it. It connects you with the largest communities of adventure creators and handles the entire process from start to finish. Creators click here: https://popf.ly/longrunlabscreators [https://popf.ly/longrunlabscreators]. Brands click here: https://popf.ly/longrunlabsbrands [https://popf.ly/longrunlabsbrands]

The Accidental Business Owner Who Built the Science of Endurance Fueling

Andy Blow didn't set out to build a company. He set out to stop ending up in the medical tent. As a triathlete who kept collapsing in the heat, Andy discovered that electrolyte loss is deeply individual, got a sweat test, changed his nutrition, and realized that what he needed didn't exist for other athletes either. Fifteen years later, Precision Fuel and Hydration is one of the most trusted names in endurance sports nutrition, working with elite athletes from Rachel Entrekin to Caleb Olson to the Ironman World Championships. Andy joins Long Run Labs to talk about the science, the business, and everything in between, including what it actually took to survive long enough to build something real. Jon and Andy chat about: * why Andy kept ending up in the medical tent and what it taught him about individual fueling * how Precision Fuel and Hydration started as a sweat test, not a product * the three levers every endurance athlete needs to understand: carbs, fluid, sodium * Rachel Entrekin, Cocodona, and what longitudinal field data actually shows * why the business nearly died more than once and what kept it going * how their Ironman partnership started with a confrontation with Ironman's legal team * building athlete rosters around authenticity, not follower counts * the F1 years and what endurance sports can learn from motorsport * why Andy stepped out of the CEO role and what that transition looked like The Huddle: If you're at the point where going at it alone isn't working or you're ready to level things up in your business, go to https://findmyhuddle.com/ [https://findmyhuddle.com/] and fill out the application Popfly: If you're a brand trying to reach outdoor, travel, and adventure audiences, Popfly is where to do it. It connects you with the largest communities of adventure creators and handles the entire process from start to finish. Creators click here: https://popf.ly/longrunlabscreators [https://popf.ly/longrunlabscreators]. Brands click here: https://popf.ly/longrunlabsbrands [https://popf.ly/longrunlabsbrands] Eternal - The app I've been waiting for is finally here. Your labs, your wearable, your training, all in one place that actually does something with it. Download Eternal Health in the app store at https://apps.apple.com/us/app/eternal-health/id6504541107 [https://apps.apple.com/us/app/eternal-health/id6504541107]

Des Linden: Build the Audience. The Deals Follow.

Des Linden has spent two decades figuring out how to build a career that outlasts the finish line. The 2018 Boston Marathon champion joins Long Run Labs to talk about the business of being an endurance athlete, what loyalty actually looks like in a long-term brand partnership, and why non-endemic deals are some of the most underrated opportunities in the sport. The conversation covers the real mechanics of how Des thinks about partnerships, content, and the transition from road to trail, plus an honest look at what it takes to stay relevant and build something lasting when the competitive chapter starts to wind down. Jon and Des chat about: * how Des started seeing the business side of running as early as 2011 * what 20-plus years of loyalty with Brooks actually looks like in practice * the difference between endemic and non-endemic brand deals and why the slow burn pays off * why host-read, unscripted ad reads outperform scripted ones * the digital twin of Des's heart and what TCS built with it * CPMs, pilot deals, and how to let the math make the case for you * YouTube as a long-form storytelling tool, not a vlog machine * the trail running boom and why Des is entering that space carefully * gravel running as an untapped middle ground for brands and audiences * financial literacy as one of the most overlooked gaps in professional running * angel investing, equity deals, and when skin in the game changes how you show up * why Yeti Coolers is the dream partnership Des hasn't pitched yet This episode is supported by: The Huddle: If you're at the point where going at it alone isn't working or you're ready to level things up in your business, go to https://findmyhuddle.com/ [https://findmyhuddle.com/] and fill out the application Popfly: If you're a brand trying to reach outdoor, travel, and adventure audiences, Popfly is where to do it. It connects you with the largest communities of adventure creators and handles the entire process from start to finish. Creators click here: https://popf.ly/longrunlabscreators [https://popf.ly/longrunlabscreators]. Brands click here: https://popf.ly/longrunlabsbrands [https://popf.ly/longrunlabsbrands] Eternal: If you've ever wished your labs, your wearable, and your training data all lived in one place and actually told you what to do with it, Eternal is it. The new version of the app gives you real guidance, not just another dashboard, and turns your health data into an actual podcast episode about your numbers. The core experience is free, and if you train at altitude, the $39 energy panel covering ferritin and B12 is a no-brainer. Download Eternal and connect your data at Eternal Health in the app store.

Why the Future of Endurance Brands Is Community, Trust, and AI | Randi Zuckerberg

Randi Zuckerberg has spent her career at the intersection of technology, media, storytelling, and entrepreneurship. But in recent years, endurance sports have become just as central to how she thinks about leadership, business, and personal growth. Fresh off a 10-hour PR at Cocodona 250, Randi joins Long Run Labs to talk about why ultra-endurance racing and entrepreneurship require many of the same skill sets: resilience, adaptability, team building, and learning how to stay calm while solving problems in real time. The conversation also dives deep into AI, the future of media, niche communities, brand trust, and why emotional connection is becoming one of the most important differentiators in business. Jon and Randi chat about: • how Cocodona became a team effort instead of just a solo race • the overlap between endurance sports and entrepreneurship • her “pick three” framework for prioritization • angel investing at the intersection of AI and endurance sports • why she invested in brands like Janji and Laurel • how AI is reshaping startups and software development • the future of niche media and long-form content • why trust and emotional connection matter more than ever • how brands can use AI to better understand community behavior • the difference between external validation and intrinsic motivation• redefining success in your 40s • why endurance sports changed her relationship with ambition This episode is supported by: ⁠The Huddle⁠: If you’re at the point where going at it alone isn’t working or you’re ready to level things up in your business, go to https://findmyhuddle.com/ and fill out the application ⁠Popfly⁠: If you’re a brand trying to reach outdoor, travel, and adventure audiences, Popfly is where to do it. It connects you with the largest communities of adventure creators and handles the entire process from start to finish. To learn more: ⁠Creators click here: https://popf.ly/longrunlabscreators⁠. ⁠Brands click here: https://popf.ly/longrunlabsbrands⁠ If you’re in Boulder for BolderBoulder week, come hang with us at two community events: • Thursday, May 21 at Skratch Labs Table: free shakeout run with Chelsea Sodaro and the MomForward Movement benefiting For All Mothers, followed by a live FTLR panel with Chelsea and Kara Goucher. Raffle prizes from On, Coros, Rapha, and Oiselle. Learn more here: https://www.movemint.cc/events/momforward_movement_unlockingyes • Friday, May 22 at Otto and Co on Pearl: “Fueling the Long Run,” presented by ProBio and FTLR with Hillary Allen, Charlie Sweeney, and Dr. Marc Bubbs. Shakeout at 6:30 p.m., panel at 7:15 p.m. Proceeds benefit the Colorado Athletics Project. Learn more here: https://www.movemint.cc/events/probio-fueling-the-long-run

Rethinking Outdoor Apparel for a Warming World | Doug Waters

Doug Waters didn’t set out to build another outdoor apparel company. He set out to solve a problem he kept running into himself. Doug is the founder of Terlingua Threads, a hot-weather adventure apparel company focused entirely on performance in extreme heat. After careers in consulting and the automotive industry, Doug found himself questioning why so much outdoor gear was still designed around cold weather while races, hikes, and outdoor adventures continued getting hotter. Jon and Doug talk about what it actually looks like to launch a product-first brand from scratch, why climate adaptation is becoming unavoidable in outdoor sports, and the realities of bootstrapping a physical product business in 2026. Jon chats with Doug about:• visiting all 63 U.S. national parks• how Big Bend National Park sparked the idea for Terlingua Threads• why most outdoor apparel still prioritizes cold weather• designing apparel specifically for 90°+ conditions• balancing performance, safety, and sustainability• building a brand around natural fibers instead of synthetics• bootstrapping vs. raising outside capital• why retaining creative control matters• product-led growth and learning from elite endurance athletes• using craftsmanship and storytelling instead of AI-generated marketing• the future of small business and independent brands This episode is supported by: ⁠The Huddle⁠: If you’re at the point where going at it alone isn’t working or you’re ready to level things up in your business, go to https://findmyhuddle.com/ [https://findmyhuddle.com/] and fill out the application ⁠Popfly⁠: If you’re a brand trying to reach outdoor, travel, and adventure audiences, Popfly is where to do it. It connects you with the largest communities of adventure creators and handles the entire process from start to finish. To learn more: ⁠Creators click here: https://popf.ly/longrunlabscreators [https://popf.ly/longrunlabsbrands%E2%81%A0]⁠. ⁠Brands click here: https://popf.ly/longrunlabsbrands⁠ [https://popf.ly/longrunlabsbrands%E2%81%A0]