In this episode of the Free Outside Podcast, I sit down with Matthew Shepard—better known as Shep—to talk all things trail running, ultra-endurance racing, and his incredible journey in the outdoors. From growing up wandering the wilderness with a rifle in hand to becoming a standout competitor in backyard ultras and the Director of Field Operations at Sinister Sports, Shep’s story is nothing short of inspiring.Follow Shep online: https://www.instagram.com/go_shep/We dive into the unique dynamics of backyard ultras, Shep’s strategies for enduring multi-day races, and some of his wildest encounters in the Canadian Rockies—like finding a fresh moose carcass and rerouting trails to avoid bears. He shares how he balances racing with his role at Sinister Sports, including the behind-the-scenes work of creating epic 200-mile races.We also discuss the mindset it takes to embrace failure, the joy of pushing boundaries, and how challenges like these make life richer. Shep talks about his plans for the Wild Horse 200 in Wales, while I reflect on my adventures, including the Pacific Northwest Trail and Great Western Loop.takeaways-Shep has been passionate about the outdoors since childhood.-Wildlife encounters can be both fascinating and challenging during races.-The backyard ultra format allows for a unique pacing strategy.-Camaraderie among racers is crucial in long-distance events.-Mental challenges are a significant aspect of racing.-Visualization techniques can enhance performance in races.-Failure is an essential part of the racing experience.-Crew support is vital for success in long-distance events.-Shep emphasizes the importance of adaptability during races.-The trail running community is growing rapidly, with exciting new eventsChapterskeywords: trail running, backyard ultra, wildlife encounters, mental challenges, camaraderie, Sinister Sports, long-distance racing, Shep, World Team Championship, racing strategies