The Trailhead

Dillon Osleger is a geologist, professional mountain biker, and longtime trail steward whose debut book, Trail Work: Restoring the Paths and Stories of America's Public Lands, uncovers the buried history beneath the trails we run, ride, and take for granted. In this conversation, Zoe and Brendan get into why nobody wants to do the unglamorous work of maintenance (and the Kurt Vonnegut line that nails it) and how to read a trail like a layered history book. Dillon decodes what is hiding in plain sight, from barbed wire patents that date a fence to within two years, to the segregated CCC camps you can spot in the stonework, to the Indigenous place names that outlast every map. Along the way: what is quietly erasing two-thirds of America's historic trails, an extremely unhinged riff on trailmaxing as the next men's wellness trend, and a genuinely useful answer to the question most of us are too sheepish to ask, which is how do you actually start doing trail work. This episode is brought to you by Running Warehouse, your one-stop shop for trail shoes, vests, poles, and the anti-chafe stuff you forget until mile 40. Join the UltraSignup Club. The Trailhead is part of the UltraSignup Podcast Network.

Romy Ancona is a DJ, trail runner, and the force behind Broken Arrow's famously joyful finish line. Born in Cozumel and now based in Colorado's Roaring Fork Valley, Romy learned to mix on a trackpad on their mom's Windows laptop before somehow landing their first gig at a Maxim Magazine party in Hollywood. These days, they split time between spinning tracks on the mountain and chasing vertical on skis and trails. In this conversation, Romy talks about shedding DJ ego, their work on Broken Arrow's inclusivity advisory council (think glitter, bubbles, and rainbow slip-and-slide dreams), and how a 2022 accident that broke their back reshaped their relationship to running. As they put it: as much as moving hurts, not moving hurts more. Plus: the lost art of the mixtape, why they watch pro paintball on the treadmill, and a running playlist spanning Celia Cruz to Limp Bizkit. This episode is brought to you by Running Warehouse, your source for jackets, gloves, headlamps, and reflective gear to get you through the dark, cold months. Race Spotlight: Registration is open for the Mount Mitchell Heartbreaker—50 miles and 12,000+ feet of climbing through stunning North Carolina single track. Sign up at ultrasignup.com.

Raziq Rauf didn't set out to become a running writer, he set out to avoid burnout as a music journalist covering London's metal and hardcore scene. Now, through his newsletter Running Sucks, he brings that same critical eye to the running industry, asking where authentic culture ends and brand activations begin. We talk about his transition from music journalism to running writing, how to spot the difference between meaningful community and manufactured hype, and discover there's exactly one death metal cowboy concept album in existence, the perfect metaphor for niche subcultures like running. This episode is brought to you by Running Warehouse, helping you stay warm and visible through winter with jackets, headlamps, and gear that keeps you honest about getting out the door. Our featured race is the Zion Ultras on April 11th, 2026, five distances through desert mesas with thousand-foot sandstone cliffs. Registration closes April 8th at UltraSignup.com. The Trailhead is part of the UltraSignup Podcast Network.

What kind of person dreams up the hardest race on earth, and then follows it up with one of the weirdest? This week on The Trailhead, Zoë and Brendan dive deep into the mind of Lazarus Lake, the man behind both the Barkley Marathons and Big's Backyard Ultra. Our guest, author Jared Beasley, joins to talk about his new book on Laz, unpacking the mystery, mischief, and mythology that made one man's backyard into a global endurance phenomenon. We explore what drives people to suffer on purpose, why Laz's races capture our collective imagination, and what they say about the culture of ultrarunning itself. 🏃‍♀️ Featured Race: Yankee Springs Winter Challenge — 50K, 25K, 10K, and 5K distances in Middleville, Michigan on January 3, 2026. A beautiful, snowy loop through Yankee Springs State Recreation Area. Fast course, frosty singletrack, and plenty of aid. 👉 Register now on UltraSignup. 👟 Presented by: UltraSignup, check out all our podcasts! 💥 Sponsored by: Running Warehouse — your source for the best shoes, gear, and deals in trail and ultrarunning.

Joe Grant has always blurred the lines between athlete and artist. From racing UTMB and Hardrock to biking between Colorado 14ers, Joe's career has evolved into something bigger than competition—projects that fuse endurance, place, and creativity. In this conversation, Joe joins hosts Zoë Rom and Brendan Leonard to talk about his journey from racing to FKTs to local San Juan projects, why he ditched the watch, and how he balances gear geekery with poetry and film photography. If you've ever wondered how running can fuel creative work—or vice versa—this episode goes deep into what it means to truly be present on the trail. Thanks to Running Warehouse for sponsoring The Trailhead! And check out the Best Day Ever Ultra, register now to reserve your spot! 👉 Subscribe to The Trailhead wherever you get your podcasts. 📺 Watch full episodes on YouTube. 🎧 Check out other shows on the UltraSignup Podcast Network: The Buzz with Buzz Burrell — grounded takes on the big ideas shaping trail and ultrarunning. Between Two Pines — conversations that connect trail running with culture, community, and the outdoors.

Take our listener survey! It takes just five minutes, and your input helps shape the future of UltraSignup! Take it here: https://docs.google.com/forms/d/e/1FAIpQLSeCgLdj8-92G_pLDxkPfuJ0-r477MzZPieRx_qlj1cmP2oybA/viewform?usp=header This week on The Trailhead, Zoë and Brendan sit down with writer, runner, and trail storyteller Sarah Lavender Smith. Sarah has been chronicling the culture of trail and ultrarunning for more than 15 years, from writing for early trail mags to her popular Substack newsletter Mountain Running and Living. She joins us to talk about how she went from journalism to the trails, and how running became not just a sport but a second career. Sarah opens up about what it means to write honestly about midlife and aging, how she's rethinking her relationship with alcohol, and why acceptance is sometimes the hardest training block of all. She also shares the story of finishing Hardrock at 56 and why stage racing like the Grand to Grand Ultra has become her true test of endurance. Along the way, we get into parenting at aid stations, practicing maximum enthusiasm, and how she's turning all of this into her next big project: a memoir. It's a conversation about resilience, storytelling, and the strange joy of chasing meaning in the mountains, sometimes through suffering, sometimes through laughter, but always through a love of the trail. Thanks to Running Warehouse for sponsoring The Trailhead! This week's featured race, Go Wild! Marin Challenge.

Love our podcasts? Help us make them even better! Take our quick UltraSignup Podcast Listener Survey! What happens when a road marathoner tackles one of the wildest ultra challenges out there, solo? In this episode, Zoë and Brendan sit down with Tommie Runz (@tommie_runz): plant-based athlete, podcast host, father, and (accidentally?) ultra-endurance legend. Tommie didn't grow up running, but after choosing sobriety in 2017, he found clarity, purpose, and eventually, a new identity in the miles. We trace his journey from gym rat to six-star marathon finisher to taking on The Speed Project solo—six ultramarathons in six days across the desert, with no prior experience beyond 26.2. He opens up about recovery (physical and emotional), the myth of "rock bottom," and how a surprise video from his kids mid-race broke him down, and gave him the strength to keep going. Also: vegan aid station food, the case for trekking poles on pavement, and whether road ultras are actually super hardcore. Thanks to our partners at LMNT – A tasty electrolyte drink mix with everything you need and nothing you don't. Get a free sample pack on us! Check out the Kismet Cliff Run to experience on of the Beast Coast's coolest trail races! Race is September 14, registration is open now!