dylan@freetrail.com
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Episodes: 162
Frequency: Weekly
Rating: 4.8/5.0
Estimated listeners: 1k-10k
Gender skew: Male
Location: USA
YouTube: 1.6k subscribers
dylan@freetrail.com
For verified host and producer emails, sign up to view.
Aaron Lutze - Host of Second Nature; described as co-host with Dylan Bowman of "The business of outdoor."
Dylan Bowman - Host of Second Nature; described as co-host with Aaron Lutze of "The business of outdoor."
Mattie Sims - Brand-building Framework; Positioning And Customer Worries; Building Versus Looking Branded; Category/niche Strategy; Product Strategy And Cultural Movement Around Excellence.
Christian Meier - Co-building Chance; Athlete-driven Entrepreneurship; Startup Scaling Alongside Other Ventures.
Tom Austen - Treating Sun As A Performance Variable; Brand Origin Story; Crossing Categories; Building High-growth Brands In A Small Ecosystem.
John Walker - Founding Pathway And Growth Of Non-alcoholic Beer Category Through Brewing Community Connections.
Bill Shufelt - Non-alcoholic Beer Category Creation; Research-to-launch Journey; Investor/distribution Hurdles; Grassroots Field Marketing; Category Competition And Redefining Success.
The One Question Every Brand Needs to Answer
June 19, 2026
Mattie Sims has built brands at Lululemon, Electronic Arts, Reef, and Rally Pickleball — and along the way developed a framework for brand building that most founders skip entirely. Now she's applying everything she's learned to two ventures at once: Courier, a performance sock brand built around the idea of the "Renaissance athlete," and Mate the Agency, a brand strategy firm working with founders across industries. In this conversation, Mattie walks through the muse framework she learned at...
The Sunscreen Brand That's Rewriting Performance Science
June 12, 2026
Tom Austen is the founder of Pelotan, the world's first sun performance brand, and co-founder of Chance, a trail running apparel brand he's building with pro athlete and serial entrepreneur Christian Meier. Both brands are based in Girona, Spain — a two-square-kilometer pocket of world-class endurance athletes, cafes, and startups that's become the Boulder of Europe. In this conversation, Tom walks through how Pelotan went from a sunburn problem on training rides to winning two Tour de France...
Behind The Brand: Athletic Brewing
June 05, 2026
Bill Shufelt was a hedge fund analyst who didn't drink, couldn't find a non-alcoholic beer worth ordering, and one night his wife spun him around on a sidewalk and told him to do something about it. Eight years later, Athletic Brewing has 300 employees, four breweries, over a million barrels of capacity, and has almost single-handedly turned non-alcoholic beer from a stigmatized afterthought into 20% of all beer at Whole Foods. In this conversation, Bill walks through the full journey: the tw...
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