#120 Tim Tollefson | Betting on Yourself, Building Mammoth Trail Fest, & The Courage to Reinvent

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"I basically didn't do it forever out of fear."

Tim Tollefson has spent the last decade proving that growth often lives on the other side of discomfort.

A two-time Olympic Marathon Trials qualifier, UTMB podium finisher, physical therapist, trail running pioneer, and founder of Mammoth Trail Fest, Tim's journey has been anything but linear. In this conversation, he shares how a career built around performance eventually evolved into something much bigger: community, connection, and learning to define success on his own terms.

Tim reflects on his transition from road marathoning to trail running, his years with Nike Trail, HOKA, and Craft, and the lessons learned from competing at the highest levels of the sport. The conversation also dives deep into confidence versus courage, the power of self-belief, and what it took to finally bring his long-time dream of Mammoth Trail Fest to life.

Throughout the episode, Tim offers a refreshing perspective on reinvention, entrepreneurship, and why betting on yourself is often the hardest—and most rewarding—decision you'll ever make.

In This Episode

• Transitioning from marathon running to trail running

• The early days of Nike Trail and racing in Europe

• Confidence vs. courage and finding self-belief

• Why athletes need an identity beyond performance

• Building Mammoth Trail Fest from an idea into reality

• Lessons learned from Nike, HOKA, and Craft

• The future of trail running and protecting its culture

• Community, connection, and creating opportunities for others

This episode is a reminder that growth rarely comes from playing it safe. Sometimes the biggest breakthroughs happen when you stop waiting for permission and start leaning in.

Timmy's Links:

IG ⁠@timtollefson⁠

⁠Mammoth Trail Fest⁠ - ⁠https://www.mammothtrailfest.com⁠

Relevant Links:

The Mammoth 200⁠ https://www.themammoth200.com⁠

Craft Sportswear⁠ https://www.craftsports.us⁠

UTMB Mont-Blanc ⁠https://utmb.world⁠

Broken Arrow Skyrace⁠ https://brokenarrowskyrace.com⁠

The Rut Mountain Runs⁠ https://runtherut.com⁠

Billy Yang⁠ https://billyyang.com⁠

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Tim Tollefson, Mammoth Trail Fest, Mammoth 200, UTMB, Nike Trail, HOKA, Craft Sportswear, Olympic Marathon Trials, trail running, ultrarunning, endurance sports, entrepreneurship, betting on yourself, confidence, courage, self-belief, identity, personal growth, community, race directing, Mammoth Lakes, Eastern Sierra, mentorship, storytelling, performance, resilience, trail culture, Free Trail, Rest Day Live