Beyond The Trailhead

craig obrist
  • 5.0 (3)
  • Entrepreneurship

Beyond the Trailhead Podcast is where the outdoor world comes alive. We sit down with the people shaping the industry—founders, designers, and adventurers—to hear the stories behind the gear and the journeys that inspire it. From trailhead conversations to trail-tested reviews, this series dives into what makes the outdoor community unique, real, and worth exploring. Whether you’re a gear junkie, a weekend warrior, or someone who just loves trail talk, this is your spot to discover what’s happening beyond the trailhead. Guest suggestions or you would like to be on the show email at info@craigobrist.com

  1. 4d ago

    Skyview Tents Founder Joe Bissonnette | Beyond the Trailhead Podcast Ep. 39

    In this episode of Beyond the Trailhead, I sit down with Joe Bissonnette, founder of Sky View Tents, a Colorado-based tent company building what Joe calls a true stargazing tent. Sky View Tents started from a simple frustration: Joe loved sleeping under the stars, but hated the usual rainfly problem. If you leave the fly off, you get the incredible open-sky experience — but you risk bugs, critters, wind, and a surprise 2 a.m. rainstorm. If you put the fly on, you stay protected — but you lose the stars. So Joe designed a tent with a patent-pending internal rainfly system that can be opened or closed from inside the tent in seconds. The result feels like cowboy camping, but with mesh protection, bug protection, and fast weather coverage when conditions change. We also dive into: • How Sky View Tents started from a late-night beach stargazing idea • Why Joe thought most “stargazing tents” were just normal tents • How the internal rainfly system works • Why clear mesh matters so much for the experience • The challenge of designing a tent that feels open but still handles weather • Why Gen 1 started as more of a fair-weather tent • How Gen 2 was tested in heavy Oregon coast rain and Buena Vista wind • The reality of sewing tents by hand while trying to run a business • Why Joe had to move from local production to factory production • The stress of raising money before the business ran out of cash • Why getting into stores could be huge for Sky View Tents This episode is full of invention, product design, startup stress, stargazing, tent talk, and honest lessons from a founder still deep in the grind. If you’ve ever stared at your rainfly and thought, “I wish I could see the sky right now,” this one is for you. Connect with Sky View Tents Website: https://skyviewtents.com Instagram: https://www.instagram.com/skyviewtents Facebook: https://www.facebook.com/skyviewtents LinkedIn: https://www.linkedin.com/company/skyviewtents YouTube: https://www.youtube.com/channel/UCxkkYqB79iQaiEZ-FJbtuZA TikTok: https://www.tiktok.com/@skyviewtents Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15.

    Skyview Tents Founder Joe Bissonnette | Beyond the Trailhead Podcast Ep. 39

  2. Jul 7

    Hest Founder and CEO Aaron Ambush | Beyond the Trailhead Podcast Ep. 38

    In this episode of Beyond the Trailhead, I sit down with Aaron Ambuske, founder and CEO of HEST, the outdoor comfort brand known for premium camping mattresses, pillows, chairs, and sleep systems built to make sleeping outside feel a lot more like sleeping at home. Aaron has been in the outdoor industry for more than 30 years, starting in Jackson Hole, working in product design, and eventually spending 18 years at K2 Skis, where he worked on skis, ski boots, poles, snowboards, and the full product development process. The idea for HEST came from a simple pain point: Aaron was getting ready for a river trip and dreading the usual air mattress routine — finding holes, figuring out how to pump it up, and knowing he probably wasn’t going to sleep well. That frustration led him to research what makes a home mattress comfortable: pressure point relief, body alignment, and temperature regulation. From there, HEST was born. We also dive into: • How HEST started from one real camping problem • Why air mattresses work for backpacking but not always for car camping • What outdoor brands can learn from home mattress design • Why Aaron believes prototypes matter more than focus groups • How HEST launched with only 75 sleep systems • Why customers pulling out a credit card is the real test • How REI discovered HEST early on • The difference between DTC and brick-and-mortar retail • Why cash flow can be one of the hardest parts of building a product brand • How HEST is helping people enjoy the outdoors through comfort This episode is packed with outdoor product design lessons, startup reality, camping comfort talk, and honest advice for anyone building a physical product brand. If you’ve ever woken up camping with a sore back, a deflated air mattress, or the thought “I love camping… but I hate sleeping out here,” this one is for you. 🛏️ Connect with HEST Website: https://hest.com Shop Mattresses: https://hest.com/pages/mattresses-collection Instagram: https://www.instagram.com/hestoutdoors Facebook: https://www.facebook.com/hestoutdoor Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15.

    Hest Founder and CEO Aaron Ambush | Beyond the Trailhead Podcast Ep. 38

  3. Jun 30

    Ripstop By The Roll Marketing Director Jameson MacFarland | Beyond the Trailhead Podcast Ep. 37

    In this episode of Beyond the Trailhead, I sit down with Jameson MacFarland, Marketing Director at Ripstop by the Roll, live from Switchback in New Orleans. If you’ve ever made your own gear, dreamed about starting a cottage brand, or wondered where small outdoor companies get technical fabrics like ripstop nylon, Dyneema®, X-Pac, mesh, webbing, and pack materials, there’s a good chance you’ve heard of Ripstop by the Roll. Jameson shares how Ripstop by the Roll started with DIY hammock makers who simply couldn’t find the fabric they wanted. What began with rolls of hammock fabric has grown into a company that helps everyone from backyard makers and MYOG hobbyists to outdoor brands designing custom materials for real production. We also dive into: • How Ripstop by the Roll started in the hammock camping world • Why hammock people might be the nerdiest gear people on earth • What “one yard to one million yards” really means • How small brands can prototype without buying massive fabric minimums • Why the right fabric can make or break a product • The difference between lab specs and real-world performance • What goes wrong when custom fabrics do not cooperate • The hilarious “bird’s nest” fabric development disaster • Why Ripstop helps makers choose what they need, not just what they want • How DIY makers and cottage brands keep pushing outdoor gear forward This episode is a fun look into the fabric side of the outdoor industry — the part most of us never think about until we start asking why one pack feels better, lasts longer, stretches differently, makes less noise, or handles weather better than another. If you’ve ever thought, “I could make that,” this one is for you. Connect with Ripstop by the Roll Website: https://ripstopbytheroll.com Instagram https://www.instagram.com/ripstopbytheroll/ Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15. Don’t forget to: • Like 👍 and Subscribe 🔔 • Share this with your hiking crew Let’s go Beyond the Trailhead.

    Ripstop By The Roll Marketing Director Jameson MacFarland | Beyond the Trailhead Podcast Ep. 37

  4. Jun 23

    GreenBelly Meals CEO & Creator Chris Cage | Beyond the Trailhead Podcast Ep. 36

    In this episode of Beyond the Trailhead, I sit down with Chris Cage, CEO and creator of Greenbelly Meals, the backpacking food brand known for ready-to-eat, high-calorie meal bars made for hikers, thru-hikers, bikepackers, climbers, and outdoor adventurers. Chris did not start out in the food world. After college, he worked as an accountant, realized it was not the path he wanted long-term, saved up money, quit, and spent nearly two years traveling, volunteering in Asia, bicycle touring through New Zealand, and eventually thru-hiking the Appalachian Trail. After all of that, he came home with very little money left, moved back in with his parents, and started experimenting with backpacking food ideas in his mom’s kitchen. The first concept was a high-calorie “gloop” made with peanut butter, honey, and anything else he could pack calories into. Eventually, that idea turned into Greenbelly Meals. We also dive into: • Why Chris left accounting and chose adventure instead • How the Appalachian Trail inspired Greenbelly • Why early Greenbelly recipes started in his mom’s kitchen • What it was like working with a food scientist • The stress of making food, shipping orders, and doing everything himself • How Kickstarter helped Greenbelly get off the ground • Why Joe Rogan gave the brand a major bump • How SEO helped Greenbelly grow in the early years • Why Chris started putting his face behind the brand • The pros and cons of direct-to-consumer vs retail • Why YouTube became a major marketing channel for Greenbelly This episode is full of founder lessons, trail food talk, business mistakes, marketing strategy, and honest insight into what it actually takes to build an outdoor food brand. If you’ve ever eaten something terrible on trail and thought, “There has to be a better way,” this one is for you. Connect with Greenbelly Meals Website: https://www.greenbelly.co YouTube: https://www.youtube.com/@Greenbelly Instagram: https://www.instagram.com/greenbellymeal Facebook: https://www.facebook.com/GreenbellyMeals Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com

    GreenBelly Meals CEO & Creator Chris Cage | Beyond the Trailhead Podcast Ep. 36

  5. Jun 16

    Overwatch X Rescue CEO & Creator Greg Pearson | Beyond the Trailhead Podcast Ep. 35

    Use Code BEYOND15 to get 15% off Overwatch x Rescue! You need this! In this episode of Beyond the Trailhead, I sit down with Greg Pearson, CEO and creator of Overwatch x Rescue, a 24/7 emergency assistance subscription service built for people who live, work, and play beyond reliable cell service. Greg’s background is not your typical outdoor startup story. He spent years working in the world of risk, crisis response, military, law enforcement, private security, and global emergency operations before creating a service designed to answer one simple question: “I need help… what now?” Overwatch x Rescue was created to help coordinate emergency assistance and help cover the financial exposure that can come with a rescue, ambulance transport, helicopter evacuation, or other emergency response situation. Greg explains why many hikers hesitate to call for help, why rescue bills can be terrifying, and how Overwatch x Rescue works differently from traditional insurance models. We also dive into: • What Overwatch x Rescue actually does • Why satellite signal alone does not get you rescued • How their 24/7 emergency response system works • Why hikers hesitate before pressing SOS • The difference between insurance and first-payer rescue support • How Overwatch x Rescue connects with Globalstar and SPOT devices • Why more smartphones may soon have satellite connectivity • How Greg built a service around crisis response and human decision-making • Why preparation matters before you ever hit the trail • The future of outdoor safety and backcountry rescue This episode is a great one for hikers, backpackers, travelers, hunters, overlanders, paddlers, photographers, and anyone who spends time outside cell service. If you’ve ever wondered what actually happens after you hit SOS… this one is for you. 🚨 Connect with Overwatch x Rescue Website: https://overwatchxrescue.com Instagram: https://www.instagram.com/overwatchxrescue Facebook: https://www.facebook.com/overwatchxrescue LinkedIn: https://www.linkedin.com/company/overwatch-x-rescue Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15.

    Overwatch X Rescue CEO & Creator Greg Pearson | Beyond the Trailhead Podcast Ep. 35

  6. Jun 9

    Why Small Outdoor Brands Struggle to Grow Online | Beyond the Trailhead Podcast Ep. 34

    In this episode of Beyond the Trailhead, I sit down with Bekah Whitney, owner and creator of Ecoteric Marketing, a marketing agency focused on helping eco-conscious outdoor brands build marketing systems that actually get executed. Bekah’s story started while living full-time on the road in a cargo trailer. She quit a stable remote job without a clear plan, picked up her first clients, and slowly built her business from freelance social media work into a full marketing agency for small outdoor brands. Now, she helps brands connect the pieces that often get separated: social media, email marketing, website messaging, blogs, customer journey, content libraries, and overall strategy. We also dive into: • Why social media alone usually isn’t enough • How small brands can stop winging their marketing • Why strategy matters before running ads • The importance of email marketing and customer journeys • Why founders need to show their face more online • How behind-the-scenes content builds trust • Why polished content is not always what performs best • The biggest mistakes small brands make with marketing • Why execution matters more than another unused Google Doc • How outdoor brands can show up consistently without losing authenticity This episode is a great one for any small brand, creator, founder, or outdoor business trying to figure out how to grow online without feeling overwhelmed. If you’ve ever said, “We need to post more,” but had no real plan behind it… this one is for you. 🌿 Connect with Ecoteric Marketing Website: https://ecotericmarketing.com Contact: https://ecotericmarketing.com/contact Instagram: https://www.instagram.com/ecotericmarketing Ecoteric Marketing focuses on social media management, email marketing, blog writing, content creation, and marketing strategy for eco-conscious outdoor-focused companies. Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15.

    Why Small Outdoor Brands Struggle to Grow Online | Beyond the Trailhead Podcast Ep. 34

  7. Jun 2

    AlpackaRaft Creator & Owner Thor Tingey | Beyond the Trailhead Podcast Ep. 33

    In this episode of Beyond the Trailhead, I sit down with Thor Tingey, CEO and co-founder of Alpacka Raft, one of the most iconic brands in the world of packrafting. Alpacka Raft started after Thor completed a massive traverse through Alaska’s Brooks Range using boats that were never really built for that kind of adventure. The idea worked… but the gear didn’t. So Thor went to his mom, Sheri Tingey, who had a background in outdoor clothing design and kayaking, and asked her to build something better. That moment helped spark what would become Alpacka Raft and the modern version of packrafting we know today. We also dive into: • The early Alaska trips that started everything • Why packrafting was so limited before Alpacka • How Sheri Tingey helped design the modern packraft • The challenge of building rafts in the early days • Why Alpacka keeps manufacturing in Mancos, Colorado • How packrafts changed backcountry travel • The difference between whitewater, flatwater, and expedition boats • Why slow growth can be a smarter business strategy • The realities of running an outdoor brand through hard seasons • What happens when private equity enters the outdoor industry This episode is packed with adventure stories, business wisdom, product design insight, and a behind-the-scenes look at the brand that helped make packrafting what it is today. If you’ve ever looked at a lake, river, or remote wilderness route and thought, “I wish I had a boat right now…” this one is for you. 🚣‍♂️ Connect with Alpacka Raft Website: https://alpackaraft.com Our Story: https://alpackaraft.com/our-story Instagram: https://www.instagram.com/alpacka_raft Facebook: https://www.facebook.com/alpackaraftllc YouTube: https://www.youtube.com/@AlpackaRaft Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15.

    AlpackaRaft Creator & Owner Thor Tingey | Beyond the Trailhead Podcast Ep. 33

  8. May 26

    Gryphon Gear Creator & Owner Gary Benninger | Beyond the Trailhead Podcast Ep. 32

    In this episode of Beyond the Trailhead, I sit down with Gary Benninger, creator and owner of Gryphon Gear, a small handmade gear company known for quilts and sleeping bags built with serious warmth in mind. Gary’s story goes way back from reading about Admiral Byrd’s South Pole expeditions, to working as a research scientist at NASA, to spending more than 100 nights sleeping on snow. His love for cold-weather adventure eventually turned into a company focused on building sleeping bags and quilts that are not just light, but actually warm when the temperature drops. We also dive into: • How Gryphon Gear got started • Why Gary has such a passion for cold-weather camping • The science behind down, loft, heat loss, and overfill • Why Gryphon Gear uses 80% overfill in their bags and quilts • What a vapor radiation barrier actually does • Why condensation matters in winter sleeping bags • The difference between warmth ratings and survival ratings • Handmade gear, custom sizing, and small business realities • Why marketing is often harder than making the product This episode is packed with gear science, old-school outdoor stories, winter camping wisdom, and the kind of technical knowledge only someone like Gary can bring. If you’ve ever wondered why some sleeping bags keep you warm and others don’t… this one is for you. Connect with Gryphon Gear Website: https://www.gryphongear.com Instagram: https://www.instagram.com/gryphongear Listen to Beyond the Trailhead YouTube: https://youtube.com/@Beyondthetrailhead Apple Podcasts: https://podcasts.apple.com/us/podcast/beyond-the-trailhead/id1860050826 Spotify: https://open.spotify.com/show/11g9jx9Oyd2YSHipi0mmDy?si=72d97f11c5f64ea6 Instagram:https://www.instagram.com/beyondthetrailheadpodcast Website: https://obristimagery.com For those asking about safety gear we use outdoors you can get 15% off Overwatch x Rescue with code BEYOND15. Don’t forget to: • Like 👍 and Subscribe 🔔 • Share this with your hiking crew Let’s go Beyond the Trailhead.

    Gryphon Gear Creator & Owner Gary Benninger | Beyond the Trailhead Podcast Ep. 32
See All (39)

Ratings & Reviews

5
out of 5
3 Ratings

About

Beyond the Trailhead Podcast is where the outdoor world comes alive. We sit down with the people shaping the industry—founders, designers, and adventurers—to hear the stories behind the gear and the journeys that inspire it. From trailhead conversations to trail-tested reviews, this series dives into what makes the outdoor community unique, real, and worth exploring. Whether you’re a gear junkie, a weekend warrior, or someone who just loves trail talk, this is your spot to discover what’s happening beyond the trailhead. Guest suggestions or you would like to be on the show email at info@craigobrist.com

Information

  • Creator
    craig obrist
  • Years Active
    2025 - 2026
  • Episodes
    39
  • Rating
    Clean
  • Copyright
    © 2025 craig obrist

You Might Also Like