Second Nature

Steve Holmberg and Matt Trappe are back for a debrief on one of the biggest weeks in trail running — Broken Arrow, Western States, and everything in between at TrailCon. Steve breaks down his state-of-the-industry analysis: why trail running's rebrand from "ultra running" unlocked massive new participation, why the sport is about to fragment the way mountain biking did decades ago, and why brands chasing "max" specs are about to pivot to "right" specs built specifically for trail.
Then Matt takes listeners inside a project few people got to experience firsthand — a house in Tahoe built with Skratch and other partners, designed to bring brand leaders, athletes, and creators together without competitive walls. He explains the intention behind it, what happened when 37 of 40 people in the room spoke up during an unscripted conversation, and why some of the best moments of the week happened specifically because they weren't being recorded.
Show Notes:
Popfly for Brands: https://popf.ly/secondnaturebrands
Popfly for Creators: https://popf.ly/secondnaturecreators
Steve Holmberg: https://www.linkedin.com/in/stephenholmberg/
Matt Trappe: https://www.linkedin.com/in/matt-trappe/
Insight Accelerator: https://insight-accelerator.com/
Matter of Brand: https://amatterofbrand.substack.com/
TrailCon: https://www.trailconference.com
Tommie Runz: https://www.instagram.com/tommie_runz/
Salomon TV - Trail Dogs: https://www.youtube.com/watch?v=05sUhlxFBk0
Salomon TV - Bill Dooper: https://www.youtube.com/watch?v=OF8ZdwpnTLQ
WSJ on Trail Runners: https://www.wsj.com/style/fashion/trail-running-footwear-9d39a2c6
Broken Arrow: https://www.brokenarrowskyrace.com/
ACG: https://www.nike.com/acg
Freetrail: https://www.freetrail.com
Tantrums: https://tantrums.run/
Amazfit: https://us.amazfit.com/
Skratch: https://www.skratchlabs.com/
SF Run Co: https://store.sfrunco.com/
BPC - Brand, Product, Content:
Hilary Yang "Raise The Bar": https://www.thehilaryann.com/raise-the-bar
Marin Rift Zone EL XR: https://marinbikes.com/products/2025-rift-zone-el-xr-int
Golden Hour Racing Shirt: https://auteursportif.com/collections/golden-hour-racing-capsule
Join us on LinkedIn: https://www.linkedin.com/company/second-nature-media
Meet us on Slack: https://www.launchpass.com/second-nature
Follow us on Instagram: https://www.instagram.com/secondnature.media
Subscribe to our newsletter: https://www.secondnature.media
Subscribe to the YouTube channel: https://www.youtube.com/@secondnaturemedia

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 campground experience from scratch, and what it takes to build a hospitality brand that maintains a 4.98-star review score while scaling to 100+ locations. He also gets into the role of data versus instinct in entrepreneurship, why type two fun is a hiring requirement for his team, and why you don't have to be a sociopath to build something great.
If you've ever looked at an industry and thought "someone should fix this" — this is the episode for you.
Show Notes:
Popfly for Brands: https://popf.ly/secondnaturebrands
Popfly for Athletes: https://popf.ly/secondnaturecreators
Matt Oesterle: https://www.linkedin.com/in/oesterle/
Ramble Campgrounds: https://ramble.camp/
Next Ventures: https://www.nextventures.com/
Mel Strong on Second Nature: https://www.youtube.com/watch?v=KlcjUzrM3Jg
Callisto Media: https://www.sourcebooks.com/callisto
HipCamp: https://www.hipcamp.com/
Net Promoter Score (Term): https://www.qualtrics.com/articles/customer-experience/net-promoter-score/
Solo Stove: https://www.solostove.com/
Zendesk: https://www.zendesk.com/
The Everything Store (Book): https://amzn.to/4vpM8kx
BPC - Brand, Product, Content:
RAB: https://rab.equipment/
The Algorithm (Book): https://amzn.to/4aOzKTJ
MFM Pod - The Algorithm Author: https://www.youtube.com/watch?v=GG4TwQEYdBY
New Yorker Profile - Sam Altman: https://www.newyorker.com/magazine/2026/04/13/sam-altman-may-control-our-future-can-he-be-trusted
***
Join us on LinkedIn: https://www.linkedin.com/company/second-nature-media
Meet us on Slack: https://www.launchpass.com/second-nature
Follow us on Instagram: https://www.instagram.com/secondnature.media
Subscribe to our newsletter: https://www.secondnature.media
Subscribe to the YouTube channel: https://www.youtube.com/@secondnaturemedia

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 Rideable Now, a not-for-profit organization dedicated to helping people with disabilities and life-changing injuries access adaptive mountain bikes. He explains why modern adaptive bikes aren't a watered-down version of mountain biking — they're genuinely terrifying, capable machines that unlock every trail in the world for people who never thought they'd ride again. He also gets into the economics of £25,000 bikes, why the e-bike power race could go too far, and the moment he gave away Rideable Now's first complete bike to a father of three who had no idea it was coming.
Show Notes:
Popfly for Brands: https://popf.ly/secondnaturebrands
Popfly for Athletes: https://popf.ly/secondnaturecreators
Martyn Ashton: https://www.instagram.com/martynashton/
Rideable Now: https://www.rideablenow.com/
Bowhead Bikes: https://www.bowheadcorp.com/
Cole Bernier: https://www.instagram.com/cbreezyrides/
Annijke Wade: https://www.instagram.com/geodesicdome/
Random Tandem: https://www.youtube.com/watch?v=onoeq45G6ec
Dirty Tricks and Cunning Stunts: https://www.youtube.com/watch?v=Rd3n8-0tuHU
GMBN: https://www.gmbn.com/
Rideable Now Membership: https://www.rideablenow.com/join
Disabled Dad Of Three: https://www.instagram.com/disableddadof3/
High Fives Foundation: https://highfivesfoundation.org/
BPC - Brand, Product, Content
Topeak Digital Tire Pump: https://backcountrycreator.tnu8.net/DWBMvq
Stashed Spacerail (10% discount link): https://www.stashedproducts.com/superrider
***
Join us on LinkedIn: https://www.linkedin.com/company/second-nature-media
Meet us on Slack: https://www.launchpass.com/second-nature
Follow us on Instagram: https://www.instagram.com/secondnature.media
Subscribe to our newsletter: https://www.secondnature.media
Subscribe to the YouTube channel: https://www.youtube.com/@secondnaturemedia

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 and runners are training in heat suits before major races. He also gets into what it felt like to go from being a cog in a media machine to betting on himself in sports tech, why triathlon taught him more about business than any corporate job, and how to know when you're doing the "social run" version of your career.
Show Notes:
Popfly for Brands: https://popf.ly/secondnaturebrands
Popfly for Athletes/Creators: https://popf.ly/secondnaturecreators
Ross McGraw: https://www.linkedin.com/in/rossmcgraw/
CORE: https://corebodytemp.com/
CORE Heat Suit: https://corebodytemp.com/products/core-suit
CORE Heat Zones: https://help.corebodytemp.com/en/articles/10447111-heat-zones
Hammerhead: https://shop.sram.com/pages/hammerhead
Zwift Bike: https://us.zwift.com/collections/equipment/products/zwift-ride-smart-frame
Wahoo Software Update: https://www.bikeradar.com/news/wahoo-elemnt-firmware-update-2026
BPC - Brand, Product, Content:
World Cup - Adidas ad: https://www.youtube.com/watch?v=mJJY53qhJe0
Breathe (Book): https://amzn.to/4eBoX0f
Respire Mouth Tape: https://respire.com/
Join us on LinkedIn: https://www.linkedin.com/company/second-nature-media
Meet us on Slack: https://www.launchpass.com/second-nature
Follow us on Instagram: https://www.instagram.com/secondnature.media
Subscribe to our newsletter: https://www.secondnature.media
Subscribe to the YouTube channel: https://www.youtube.com/@secondnaturemedia

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 Lululemon and has refined across every role since — why the most important question isn't "who buys this product" but "what is this person worried about when their head hits the pillow at night." She also gets into why looking branded is not the same as having a brand, what happened when Rally discovered their customers weren't there for pickleball, and why having her son was the thing that finally convinced her she could be an entrepreneur.
Plus: why niching down is the thing every founder is most afraid of, how Courier is building a cultural movement around versatile excellence, and the Red Bull receptionist whose casual suggestion became a billion-dollar product strategy.
Popfly For Creators: https://popf.ly/secondnaturecreators
Popfly for Brands: https://popf.ly/secondnaturebrands
Show Notes:
Mattie Sims: https://www.linkedin.com/in/madeline-sims-83385823/
Courier Socks: http://couriersocks.com/
Mate The Agency: https://www.matetheagency.com/
Rally Pickleball: https://www.rallypickleball.com/
Mate IG Carousel Link: https://www.instagram.com/p/DYW4_SVEU8b/
Carrie Rheaume (Mate agency co-founder): https://www.linkedin.com/in/carrie-rheaume-6376521a8/
Matt Sims: https://www.linkedin.com/in/matthew-sims-9b716450/
Gartner Hype Cycle: https://www.forbes.com/sites/johnwerner/2024/07/18/the-trough-of-disillusionment-and-four-outliers-on-the-gartner-hype-cycle/
Morgan Tuohy: https://www.linkedin.com/in/morgan-tuohy/
Dera: https://rundera.com/
Ryan Thrower: https://www.instagram.com/ryanthrower/
BPC - Brand, Product, Content:
Seniq: https://seniqbrand.com/
Summer Edition - Red Bull: https://www.redbull.com/us-en/energydrink/products/red-bull-summer-edition
Billy Oppenheimer's newsletter: https://billyoppenheimer.com/
Join us on LinkedIn: https://www.linkedin.com/company/second-nature-media
Meet us on Slack: https://www.launchpass.com/second-nature
Follow us on Instagram: https://www.instagram.com/secondnature.media
Subscribe to our newsletter: https://www.secondnature.media
Subscribe to the YouTube channel: https://www.youtube.com/@secondnaturemedia