Long Run Labs

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]⁠. ⁠Brands click here: https://popf.ly/longrunlabsbrands⁠ [https://popf.ly/longrunlabsbrands⁠]

Why Entrepreneurs Stay Stuck (And How to Actually Move Forward) | Christian Rawles

Christian Rawles didn’t just build a brand in the outdoor industry, he spent nearly two decades learning what it actually takes to run one, eventually buying and leading the business himself. Christian is now an executive coach working with entrepreneurs who want to build businesses that align with their values, not just scale for the sake of growth. His work focuses on clarity, self-awareness, and helping founders close the gap between where they are and where they want to be. Jon and Christian explore what it really looks like to build a career intentionally, and why so many entrepreneurs stay stuck even when they’re doing everything “right.” Jon chats with Christian about: • starting at the bottom and learning how a business actually works • working for free or cheap to create career inflection points • why working in the outdoor industry isn’t always what people expect • how he transitioned from founder to executive coach • the difference between being stuck and being unclear • the “gap vs. gain” framework and why it changes everything • fear of success vs. fear of failure • defining success beyond money and metrics • the role of presence, gratitude, and self-awareness • why entrepreneurs need new definitions of success Stay connected: Christian's Website: https://www.christianrawles.com/ 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/longrunlabscreators⁠]. ⁠Brands click here: https://popf.ly/longrunlabsbrands [https://popf.ly/longrunlabsbrands]⁠

Turning Community Into a Running Brand That Lasts | Nick Dibos

Nick Dibos didn’t set out to build a scalable apparel company. He set out to build something that actually means something to the people around him. Nick is the founder of Greenville Uptempo Sports, a running apparel brand rooted in community, culture, and storytelling. After careers in pharmacy and real estate, he shifted into building a brand that reflects the heartbeat of the Greenville running scene. Jon and Nick talk about what it looks like to grow a business from the inside out, starting with people, experience, and local identity rather than scale. Jon chats with Nick about: • growing up in Eugene and how it shaped his view of running culture • why Greenville’s amateur running scene feels different • building a brand from local community, not top-down strategy • the role of storytelling in creating connection • why some of the most impactful brand decisions don’t scale • handwritten notes, experience, and attention to detail • the tension between growth and staying true to the brand • how product becomes a vehicle for something deeper 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/longrunlabscreators]⁠. ⁠Brands click here: https://popf.ly/longrunlabsbrands⁠ [https://popf.ly/longrunlabsbrands⁠]

Building a Business in Trail Running Without Losing Trust | Seth LaReau

Seth LaReau didn’t set out to build a media brand. He set out to create something he wished existed. Seth is the writer behind Trailwaves, a newsletter exploring the business, economics, and culture of trail and ultra running. With a background in finance and accounting, he brings a different lens to the sport, one that blends data, curiosity, and lived experience in the trail running community. Jon and Seth talk about what it actually looks like to build something from the ground up while working a full-time job, and how to think about audience, value, and monetization without losing trust. Jon chats with Seth about: • using a finance background to analyze the trail running industry • building Trailwaves and finding the intersection of passion and expertise • imposter syndrome and why it often signals growth • creating content through curiosity instead of authority • the evolving media ecosystem in trail running • how to think about monetization without compromising authenticity • brand partnerships, affiliates, and delivering real value to an audience • investing in the outdoor industry and where the opportunity exists • building a business slowly and intentionally over time Stay connected: Follow Seth on Instagram: https://www.instagram.com/seth_lareau/ Follow Trailwaves on Instagram: https://www.instagram.com/trailwavesrun/ Subscribe to the Trailwaves Newsletter on Substack here [https://trailwaves.substack.com/?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnbpo4SXo6YRCcVOfVO4pO376812xlxdTrFZSa5Pv0lcrjQd8WfL7RlXI5Ow0_aem_h_tKNIftSnrDGNGyuxTPZw&utm_id=97760_v0_s00_e0_tv3_a1denni8r3qerc]. This episode is supported by: ⁠The Huddle⁠ [https://findmyhuddle.com/]: 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 [https://popf.ly/longrunlabsbrands⁠]: 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/longrunlabscreators]. ⁠Brands click here: https://popf.ly/longrunlabsbrands⁠ [https://popf.ly/longrunlabsbrands]