Episodes: 165
Frequency: Weekly
Rating: 4.8/5.0
Estimated listeners: 1k-10k
Gender skew: Male
Location: USA
YouTube: 1.6k subscribers
dylan@freetrail.com
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Aaron Lutze - Outdoor industry professional and co-host of Second Nature, focused on the business, brands, products, and creators shaping outdoor markets.
Dylan Bowman - Outdoor industry professional and co-host of Second Nature, focused on the business, brands, products, and creators shaping outdoor markets.
Martyn Ashton - Adaptive Mountain Biking, Nonprofit Leadership, Accessible Outdoor Recreation, And The Economics Of Adaptive Bikes.
Ross McGraw - Heat Training, Sports Technology, Athlete Performance, Career Transitions, And Commercial Leadership.
Mattie Sims - Brand Strategy, Customer Insight, Entrepreneurship, Niche Positioning, And Building Consumer Brands.
The Last Time Someone Reinvented Camping Was 1962
July 10, 2026
Matt Oesterle built his first company, Callisto Media, from zero to $85 million in revenue by using data to disrupt the book publishing industry. Then he sold it to Penguin Random House and asked himself: what's the next industry that hasn't been forced to evolve? The answer was camping — an industry whose biggest brands were founded in the 1960s and haven't changed much since. In this conversation, Matt walks through the framework he uses to pick businesses, how he designed the Ramble campgr...
Martyn Ashton on Rideable Now and the Future of Adaptive MTB
July 03, 2026
Martyn Ashton spent two decades as one of the most influential trials riders in the world — making the smallest, most niche discipline of mountain biking accessible and exciting for a global audience through videos, shows, and a personality that made everyone feel like they could try it. In 2013, a crash during a stunt show left him paralyzed. Now he's doing the exact same thing all over again — this time for adaptive mountain biking. In this conversation, Martyn walks through the founding of...
You've Heard of Heat Training. Here's How It Actually Works.
June 26, 2026
Ross McGraw has had one of the more interesting career arcs in the outdoor industry — from Nike's NYC Run program to Vice Media and Viacom, to helping build Hammerhead through its acquisition by SRAM, and now leading commercial efforts at CORE, the company changing how elite athletes think about heat. In this conversation, Ross breaks down the science of heat training in plain language — why 80% of the energy athletes generate is thermal, how heat zones work, and why the world's best cyclists...
dylan@freetrail.com
For verified host and producer emails, sign up to view.
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