The conversation revolves around the Jeffrey Awards, celebrating achievements in ultra running, including new race directors, controversies, tragic FKTs, and the Walker of the Year award. The hosts discuss various nominees and their stories, highlighting the challenges and triumphs within the ultra running community. In this engaging conversation, Jeff Garmire and Derrick Lytle explore various themes in ultra running, including speed debates, the merits of double versus single track, and the significance of awards in the community.

The Jeffrey Awards – Categories & Nominees

Most Obvious New Race Director

Joe Corcione

Tim Tollefson

Dylan Bowman (added a 100K, Big Alta)

Carl Laniak (took over Barkley Marathons)

Finn Melanson (Antelope Island Buffalo Run)

We Should Be Your Publicist Award

Grand Slam Track

Candice Burt

2025 IAU 50K World Championships (canceled two weeks out)

Black Canyon 100K (cheating scandal)

Most Tragic FKT

Becca Bergstrom – multiple PCT attempts, quick failures

John Kelly – quit the AT a few hundred miles from the end

Kristian Morgan – approximately his 128th AT attempt

Eric Hallsten – quit Washington after averaging ~70 MPD

Krista Hallsten – fastest supported double TRT, not recognized, therefore “doesn’t count”

Walker of the Year

A.J. Waller (Cocodona 250)

Matt Johnson (Texas 1000)

Troy Croxdale (“Punisher”)

Madison Blagden (“Peg Leg”)

Andrea Moore (six 200+ mile races)

Lyla Harrod (Appalachian Trail FKT)

Finally It Happened Award

Kilian Jornet uses unlimited resources for an unmatchable FKT

François D’Haene loses an FKT (Nolan’s 14 to David Hedges)

Ryan Montgomery finally earns a Golden Ticket after global race hopping

Salt Lake City gets a Western States winner

Fastest Camera Operator

Jacob Banta

Drew Darby

Derrick Lyttle

Jeff Pelletier

Matt Shapiro

Forgot It Happened Award

Seth Ruhling course record at Black Canyon

Chipotle Showdown

David Roche ran Western States (kind of)

Unbreakable movie attempt

Gorge 100K Worlds qualifier

Courtney Dauwalter DNF at Cocodona

Double Track vs Singletrack Award

Double Track

Singletrack

Who Is That Award

Will Murray

Sarah Perry (395 miles)

Caitriona Jennings (Tunnel Hill, 100-mile world record)

Most Destroyed Trail

Any trail an e-bike touches

Arizona Trail

Owner of Zona (King of Arizona)

Candice Burt – Arizona Monster

Jamil Coury – Aravaipa

Abby Hall – Western States

Jim Walmsley

Sadie Curry – AZT FKT

Courtney Dauwalter vs Jim Walmsley Award

East Coaster of the Year

Dan Green (Cocodona)

Canyon Woodward (Golden Ticket)

David Sinclair

Tori Constantine (“Chewy”, Long Trail FKT)

Xander Keiter

Andrew Drummond (White Mountain Direttissima)

Weird Moment of the Year

David Roche giving up his Golden Ticket

Candice Burt doxxing someone on livestream

Kilian Jornet crowd sourcing his next FKT

Most Air Time Award

Chris Warden

Leah Yingling

A.J. Waller

Corrine Malcolm

Joe Corcione

Hypocritical Hero Award

Michelino Sunseri pardoned

Ruth Chepngetich doping ban one year after world record

Hayden Hawks Ultra Runner of the Year Award

Caleb Olson

Hans Troyer

Jeff Mogavero

Tara Dower

Katie Schide

Abby Hall

Megan Eckert (six-day world record, 603 miles)

Bezos Most Expensive Breakup Award

Katie Schide leaving TNF

Jeff Browning leaving Altra

Trend of the Year

Icy kiddie pools

Lying about Zone 2 pace

Moving across the country

Livestream everything

Running a marathon again

Influencer of the Year

David Poach

Nick Bare

David Goggins

Cam Hanes

Jeff Pelletier

Mike Wardian

Max Jolliffe

Most Pointless Miles

Jamil Coury

Kevin Russ

Matt Johnson

Andy Glaze

Derrick Lytle Award

Jeff of the Year (Audience Nominated)

Jeff Mogavero

Jeff Galloway

Jeff Garmire

Katie Schide

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Jeff Colt is back, calling in from Carbondale with a mission to help rehabilitate the name “Jeff” one mountain town conversation at a time. We start with winter training reality in ski country, how to keep momentum when the days are short, the “subsistence” weeks that quietly save your season, and the eternal debate of pants, tights, and looking cool versus staying warm. From there it turns into a bigger conversation about identity, planning, uncertainty, and why the simplest answer sometimes is “we just have Jeff,” so we might as well make it a good one.

Then we head straight into the good stuff, the White Mountains and the Mahoosuc Traverse, where “running” becomes scrambling, crawling, and three points of contact through the Mahoosuc Notch. Jeff breaks down the history and the legends (including Chris Getz and the steak stop), why style matters as much as speed in FKTs, and how different eras and ethics shape what we celebrate. We close with one of the most fun tangents of the whole Month of Jeff, what it is really like working in the AMC huts, from responsibility in dangerous weather to full-on blanket-folding skits, including Harry Potter and Frozen, all in service of three sacred rules: fold the blankets, pack out the trash, and tip the hut crew.

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Chapters

00:00 The Jeff Identity Crisis

06:19 Winter Training in Mountain Towns

09:18 Exploring the Mahusik Range

12:37 The Legacy of Chris Getz

15:27 Navigating the Mahusik Notch

18:29 Style and FKT Philosophy

22:00 The Challenge of Self-Supported FKTs

24:56 Planning and Uncertainty in Adventure

27:57 The Evolution of Trail Running Style

42:22 Exploring Style in Trail Running

44:16 The Debate on Supported vs. Unsupported

47:43 The Evolution of Trail Running

50:54 Killian Jornet: The Pinnacle of Trail Running

54:43 Authenticity in Trail Running

58:30 The Role of Creativity in Trail Running

01:03:31 Life Lessons from Working in the Huts

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This week on the Free Outside Podcast, I am joined by Jeff Eklund, an “ordinary Jeff” calling in from North Carolina who quickly proves he is anything but ordinary. We kick things off with a Jeff quiz show where every answer is a different Jeff, and it immediately derails into the best kind of chaos.

Jeff shares his winding path into running, including randomly ripping a 3:16 at Chicago in his 40s, qualifying for Boston (and skipping it because life happened), then stepping away before coming back strong after knee replacements. He talks about what it felt like to start running again, why he refuses to accept “don’t run” as a life sentence, and his current mission to break two hours in the half marathon while stalking the competition on Strava like a proper veteran.

Then we shift into the second life arc, Jeff and his wife selling basically everything during COVID, moving into a 27-foot Airstream, and traveling to 47 states. We talk minimalism, Facebook Marketplace hustle, getting “pulled around” the country by life, and the underrated places that surprised him most, from Rhode Island to Arizona to the hidden gems of Nebraska.

Somewhere in the middle, Jeff goes full historian and takes us deep into his obsession with Theodore Roosevelt (the strenuous life, Rough Riders lore, the teddy bear origin story, and meeting a TR impersonator in North Dakota that turns into a legit hike). We also get a side quest on Fred Harvey restaurants, Harvey Girls, and old-school American road culture, plus a list of roadside oddities that feels like a hallucination timeline from mile 20 of a marathon.

We wrap with a quick masterclass in sales (relationships, listening, and handling rejection), lessons Jeff wishes he knew when he was younger, and a perfect cherry on top story about Brooks customer service, a surprise signed Scott Jurek book, and the greatest accidental Instagram mix-up of all time.

If you like running, reinvention, road trips, American history tangents, and a guest who can turn one question into six stories, this one is for you.

Chapters

00:00 The Jeff Quiz Show Begins

04:52 Jeff Eklund's Journey into Running

07:49 Overcoming Challenges and Finding Motivation

10:50 The Impact of Family on Running

13:45 Rediscovering the Love for Running

16:42 Transitioning to Life in an Airstream

19:28 Selling Everything and Embracing Minimalism

22:23 Exploring the Open Road and Human Connection

24:56 Theodore Roosevelt: A Personal Connection

26:29 Meeting the Impersonator: A Unique Encounter

28:47 The Legacy of Theodore Roosevelt

30:23 The Teddy Bear Origin Story

31:40 The Strenuous Life Philosophy

33:40 Fred Harvey and the Railroad Era

37:24 The Harvey Girls: Pioneers of the West

39:07 Underrated States: Personal Reflections

41:34 Hidden Gems in the Midwest

45:20 Exploring Unique Destinations

48:13 The Art of Selling

50:29 Reflections on Youth and Education

55:10 Customer Service and Personal Connections

01:00:18 Celebrating Ordinary Heroes

Subscribe to Substack: http://freeoutside.substack.com

Support this content on patreon: HTTP://patreon.com/freeoutside

Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF

Email me to buy a signed copy of my book, "Free Outside" at jeff@freeoutside.com

Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside

Website: www.Freeoutside.com

Instagram: thefreeoutside

facebook: www.facebook.com/freeoutside