Roadside America With Ordinary Jeff: Prairie Chickens, Hot Dogs, and Teddy Roosevelt

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

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