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.

Lindsey Freeman is a sociologist, writer, and lifelong runner whose book Running offers a feminist and queer reading of the sport. In this conversation, Zoë and Brendan talk with Lindsey about what it means to treat running as a practice, becoming yourself through repetition, staying soft, and trusting that showing up matters even when outcomes don't.

The conversation moves through ideas like the magic circle that makes it acceptable to try really hard in public, the growth of queer run clubs, and the strange emotional math of caring deeply about things that often disappoint you. There's also a delightful tangent about Stuart Murdoch of Belle and Sebastian being a serious runner. Lindsey's advice for writer's block and bonking alike? Have a snack and come back tomorrow.

Get her amazing book here.

This episode is brought to you by Fast Pickle—grab-and-go pickle juice shots at fastpickle.com—and Tantrums, makers of the Crest 6 hydration pack at tantrums.run. Plus: Ultra Trail Drakensberg in South Africa is now open for registration 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.

Nick Thompson has spent his life chasing big stories and finish lines. The CEO of The Atlantic and author of The Running Ground joins Zoë and Brendan to talk about running through life's hardest moments, from a cancer diagnosis at 30 to balancing elite training with parenthood and a high-powered media career.

Together, they explore why running became Nick's anchor through chaos and change, the strange parallels between journalism and endurance sports, and the lessons he learned from his father, and why he runs to not become him. They talk about what aging athletes get wrong about decline, the emotional threshold of a "real" ultra (and the world's shortest one), and how Nick manages to fit sub-three-hour marathons into a 60-hour work week. Along the way, Zoë and Brendan share their own thoughts on parenting as endurance training, finish-line family moments, and why run commuting deserves a comeback.

The Running Ground: A Father, a Son, and the Simplest of Sports is out now from Penguin Random House.

Sponsored by: LMNT, stay hydrated year-round with a free sample pack at drinklmnt.com/ultrasignup.

Featured Race: Peacock Gap Trail Run — a love letter to Bay Area trails at China Camp State Park.

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.

Harvard evolutionary biologist Dan Lieberman is the scientist whose work reshaped how we understand running. His research on human evolution helped popularize the idea that we're born to run, that our bodies, from our toes and tendons to our oversized glutes, are uniquely adapted for endurance. In this conversation, he joins Zoë and Brendan to explore what running reveals about being human.

This week's featured race is the Naughty Hog 100k, 50k, 25k, 10k, and 5k! Dec 20. Register now!

We dig into why ultrarunning is evolutionarily bizarre but still deeply natural, what persistence hunting really looked like, and how belly fat, treadmills-as-torture-devices, and even the barefoot craze all tie into our running story. It's part science lesson, part reminder that while we didn't evolve for nipple tape, running is still one of the most human things we do.

Thanks to LMNT for supporting The Trailhead!

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.

This week on The Trailhead, Zoë Rom and Brendan Leonard sit down with one of ultrarunning's most quietly legendary figures: Junko Kazukawa. A two-time Leadwoman, breast cancer survivor, and one of the few athletes to complete both the Grand Slam of Ultrarunning and the Leadwoman series in a single year, Junko's story is a masterclass in resilience and joy.

Born in Sapporo, Japan, and now based in Denver, Junko shares how she started running in the U.S. after coming over as a student, how she trained through cancer treatments, and why she still lines up for 100- and 200-mile races at age 62. She talks about the identity and community she's built through the sport, how her view of fitness has evolved over decades, and why she believes "glutes are everything."

We also hear about her favorite races around the world, from the Tour de Géants to Mount Fuji, and what keeps her motivated to take on new challenges even as recovery gets harder with age. Whether you're chasing your first ultra or your 26th, Junko's joy and perspective will make you want to lace up and keep going.

Thanks to Running Warehouse for supporting The Trailhead. Check out their great selection of everything from shoes to nutrition, packs and socks, with free two-day shipping.

Register now for the Antelope Canyon Ultras! These desert classics always sell out, get your spot now!

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.

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This week on The Trailhead, Zoë and Brendan sit down with writer and ultrarunner Nick Triolo, author of The Way Around: A Field Guide to Going Nowhere. From circumnavigating mountains to ditching Strava and racing for a year, Nick shares what it means to move through landscapes differently, choosing circles over summits, presence over performance, and curiosity over metrics.

We talk about why loops feel so satisfying, how creative practice overlaps with running, and what happens when you stop measuring progress and start running just to run. Plus, the crew debates their favorite loops and why "there's nowhere else to go" might be the ultimate running mantra

🏃‍♀️ Featured Race: Cowboy Yeti in Bastrop, Texas—20K loops, mild winter weather, and maybe even Brendan's birthday bash.

👟 Sponsor: Thanks to Sidas for supporting this episode. Keep your feet happy on every loop with high-performance socks, insoles, and blister protection—UltraSignup listeners get 20% off at sidas.us.