Dirtbag Rich

• Dave Whitson: long-distance walker, history teacher, writer, guide

  Dave Whitson is a 40-something high school history teacher and Camino de Santiago guidebook author who has crossed the United States on foot, spent six of the past twelve months traversing Italy, and taken countless student groups on long-distance walking adventures. He has no phone plan, gym membership, or anything resembling a vice. He writes powerful travel narratives, adores the challenge of working with sharp teenagers, struggles with relationships, thinks frequently about death, considers himself a sort of “parasite” on conventional society, and knows more about the Camino (and other modern pilgrimage routes) than pretty much anyone on earth. (davewhitson.com)Full transcript: dirtbagrich.com/dave

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• Ryan Van Duzer: YouTuber, bikepacker, motivational speaker

  Ryan Van Duzer is a 46-year-old adventurer, filmmaker, and bike-powered storyteller who has spent the past two decades turning his obsession with movement into a full-time career. (duzertv.com)After a two-year Peace Corps stint in Honduras, Ryan skipped the flight home, bought a $700 bicycle, and pedaled 4,000 miles back to Boulder, Colorado—a trip that changed his life and set him on a path toward sharing human-powered adventures with the world. What followed were years of scraping by as a travel-channel hopeful, living with his mom, chasing production gigs, and refusing to quit when every practical voice said he should.At age 36, he walked away from TV and started over on YouTube. Now he earns a six-figure income through ad revenue, Patreon, bike-design royalties, and public speaking—but he still rides everywhere, owns no car, and keeps his expenses low.We dig into the years when he lived on almost nothing, the slow grind toward creative control, and the constant tension between documenting life and living it. Ryan opens up about how his “get off the couch” mantra evolved from personal fitness to something broader: a way of rebuilding social fabric in an age of isolation.We also discuss the doubts that creep in as he ages out of being the “young, spunky YouTube adventurer,” the exhaustion of constant content creation, and why the freedom he fought for still feels worth it.Full transcript: dirtbagrich.com/duzer

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• James Brown: bicycle traveler, relational coach

  James Brown is a 43-year-old traveler, relational coach, graphic designer, and lifelong seeker caught between the urge to roam and the desire to put down roots. (jameswonders.uk)After spending his twenties and early thirties working long hours in England’s gray corporate offices—commuting three hours a day to a job he genuinely loved but a life that left him drained—James finally broke free. He quit, bought a motorbike, and rode across Europe before taking an eight-month cycling journey through Asia with his girlfriend. The trip ended their relationship but sparked something else: a realization that he could live on very little, work remotely, and make his own rules.In the years that followed, James built a flexible, purpose-driven life as a freelance designer for nonprofits while living in Italy, Costa Rica, Spain, Morocco, and Colombia. His days alternated between deep creative focus and drifting—renting apartments in tiny towns, learning new languages, and building communities he would inevitably have to leave when visas expired or restlessness returned.At the heart of James’s story is tension: between adventure and stability, freedom and belonging. He dreams of having a home base, a dog, and his own cupboard full of clothes—but he also knows that at any moment, he could sell everything and ride into the horizon again. Lately he’s been trying to understand why through the practices of "circling" and "authentic relating."We talk about how childhood restlessness can become adult wanderlust, how travel can be both healing and escapist, and how to know when "freedom" starts to look like avoidance. James reflects on the comfort of drifting, the fatigue of constant choice, and what it might take to finally stop moving—not because he’s trapped, but because he’s ready to stay.Full transcript: dirtbagrich.com/james

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• Aisha Trent: seasonal worker, minimalist, car dweller

  Aisha Trent is a 31-year-old seasonal worker, minimalist, and car dweller who’s spent the past two and a half years living out of her Toyota 4Runner—and doesn’t see herself going back. (@norent_trent)After losing both parents in a tragic car accident, Aisha decided life was too short to wait for permission. She downsized everything she owned, traded a Ford Fiesta for a 4Runner, and built a life centered on nature, healing, and independence. Now she sprays invasive weeds and algae from boats and shorelines each summer in Illinois, saving enough to take winters off for time with friends, or more recently, long solo road trips through Colorado, Oregon, and Arizona.We talk about why she prefers waking up surrounded by windows instead of walls, and how she and her boyfriend make “driveway living” work. Aisha also reflects on growing up insecure, her time in eating disorder treatment, and how outdoor simplicity became her therapy.She’s currently considering a short return to full-time work—just long enough to pay off her student loans and car debt and buy back even more freedom. But first she'll be collecting her inaugural passport stamps in Austria and the Philippines.Aisha's favorite quote: “It’s all lies. Back to nature—the only truth.” (from the music producer Rick Rubin)Full transcript: dirtbagrich.com/aisha

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• Diana Grijalva: climber, guide, dirtbag royalty

  Diana Grijalva is a 42-year-old outdoor educator, international guide, and almost-astrophysicist who hasn’t paid rent since 2008. (@diana.grigri)Diana explains how she lives on seasonal wages, why she’d rather sleep in a van or hostel bunk than clock 40 hours a week, and how flexibility lets her drop everything to show up for family when it matters.We get into her peak dirtbag years—dumpster diving, living on $7,000 a year, breaking ice off her tent in Joshua Tree—and how she’s sustained the lifestyle into her forties. Diana shares her favorite climbing hubs from Mexico to Turkey, the grind and charm of hostel life, and why she sees most jobs as “stealing people’s lives.”She also talks about the unglamorous math behind dirtbagging: stretching cheap food and used gear, picking work that covers the basics, and saying no to anything that eats into her freedom. She lights up describing her rotation of winter haunts—Joshua Tree, Red Rocks, Moab, Potrero Chico, Greece, Spain, Sri Lanka, India, Morocco—each one a way of outsmarting the cold while deepening her love for new cultures.Full transcript: dirtbagrich.com/diana

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