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

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

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

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

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

Julieta Duvall is a 42-year-old flight attendant, unschooling mom, and part-time poet who spent years chasing job security before realizing that freedom mattered more. (@the_unschooling_lifestyle)

Originally from Mexico, Julieta studied law, dropped out, and ended up taking the midnight shift as Spirit Airlines’ only Spanish-speaking reservations agent in Michigan. One year later, she joined the first class of flight attendants hired after 9/11. Today she works for Delta, earns top-of-scale pay, and chooses her monthly schedule based on her family’s needs, often dropping every assigned trip to rebuild the month from scratch.

She explains the hidden economics of flight attending—how pay is calculated, how to game the system, and why the swankiest layovers are hotly contested. Julieta also opens up about her family’s financial history: buying a $7,000 house, doing accidental landlording, weathering debt consolidation (twice), and how their motto became “spend less, don’t work more.”

We discuss how unschooling her kids changed everything—especially how she sees time, purpose, and money. She describes the shift from tiger mom to intentional parent, how her body reminds her when she’s over-pleasing, and why she’ll never again miss a family moment for the sake of someone else’s crisis at work.

We also get into her enduring love for bookstores, slow travel, and the trees of Michigan—and how she’s built a life that lets her say “no” to work, “yes” to crafting, and “maybe” to the chickens next door.

Full transcript: dirtbagrich.com/julieta

Michael Hughes is a 37-year-old river guide, training director, and year-round rafting company employee who’s built a stable yet unconventional life around whitewater. (@northwest.rafting.company)

His journey started at age 19 on a canoe float down the Rio Grande, where he realized that working on rivers could actually be a job. Michael spent his twenties chasing the guiding season between California and Oregon, stitching together odd jobs to keep returning to the water. He built chicken coops, worked wine harvests, lead students on a gap year program in India and Nepal, and never let a “real job” get in the way of summer river trips.

Now he manages a seasonal crew, runs guide training, and leads a handful of multi-day trips each summer. He lives in a camper during the rafting season in Southern Oregon and then returns north to Hood River, where he and his fiancée recently bought a house in White Salmon (technically, she's the landlord). His role includes intense bouts of hiring and logistics, but also off-season flexibility: long trail runs on weekdays, powder days in the winter, a rafting trip in Bhutan each fall, and plenty of personal river time for kayaking.

We talk about Michael's path to financial independence without family help, the tradeoffs of guiding life (like missing most summer weddings), and how he finds meaning in late-night Milky Way sightings, watching kids growing up on trips over the years, and seeing his mom jump into the river for the first time at age 60.

Michael also contributes to Whitewater Guidebook.

Full transcript: dirtbagrich.com/michael

Jack Schott is a 36-year-old summer camp consultant, former camp founder, and self-directed learning advocate who spends a lot of time thinking about money. (jackschott.com)

Jack occasionally earns $1,500-$3,500 in a single day by running corporate trainings and camp staff workshops: work that doesn’t always light him up, but work that is very useful for buying time, freedom, and very possibly, another summer camp that he can direct.

Jack describes the tension he feels between wanting to do meaningful work and not wanting to be tied down. At his most purposeful, he was co-running a camp in upstate New York with his ex, building cabins by hand and forming deep relationships with kids and staff—but he felt trapped. Now he’s trying to design a setup where he can direct a camp each summer without needing to live on site year-round.

He also shares how he thinks about money strategically: not just for personal comfort, but as a tool for long-term impact, particularly in making camps more self-directed and less top-down. In this vein, he describes how an average 22-year-old could quickly build a high-flexibility career from scratch by cold-emailing lawn care companies (or a similarly "boring," everyday field of work).

Jack is less focused on outdoor adventure than past guests, but he’s laser-focused on building a life of flexible work and purposeful contribution. His version of "dirtbag" is getting to play outside with kids, every single summer, for the rest of his life.

Full transcript: dirtbagrich.com/jack

Morgan Sjogren is a 38-year-old environmental writer who has spent the last seven years living as a modern-day desert nomad, crafting a freelance journalism career while residing primarily in the remote wilderness of Utah's Canyon Country. (morgansjogren.com)

After growing up in Southern California suburbia and spending her twenties pursuing a marketing career, Morgan left her more conventional life at age 30 to live full-time in the back of a Jeep, sustaining herself on dumpster-dived ingredients and gas station burritos. For the past seven years, she has made the Colorado Plateau her home, spending much of her time in solitude among the sandstone canyons and mesas, with just a fraction of her year in actual cities. She explains how nature became her true home rather than a playground, and how this relationship with the desert has shaped both her writing and her sense of purpose.

We discuss her path from suburban trail runner to high desert hermit and how she cobbles together income through freelance writing, photography, public speaking, house cleaning, and modelling. Morgan describes her two books—the dirtbag cookbook Outlandish and the historical narrative Path of Light—and how retracing 1920s expeditions through Glen Canyon helped her find both community and her current partner Aaron. She explains why she feels called to advocate for public lands through her writing, and how the desert has repeatedly shown her that even in apparent solitude, she is never truly alone. For Morgan, being "dirtbag rich" means having clean water, clean air, healthy ecosystems, and places that are open and welcoming to all people.

Full transcript: dirtbagrich.com/morgan

Blake Boles is a 42-year-old writer, cycle tourist, trail runner, partner dancer, and California-born temporary European expat who leads international trips for self-directed teenagers and young adults. (blakeboles.com)

In this special episode, former guest Jenny Abegg interviews Blake about what he's doing with his life, the Dirtbag Rich project, his early influences, and how he thinks about freedom, purpose, security, and more. Topics include:

• Freedom as “not being available for servitude”
• His view of long-term security and alternative retirement plan
• What the hard moments look like in a life on the road
• His undying love for the Deutschland Ticket (an unlimited travel pass covering all forms of public transport in Germany)
• How much stuff he actually owns (and the rules he sets for himself around possessions)
• Finding stability through extensive planning (and Google Calendar), and security through extensive friendships (his friend buckets include: dance, outdoors, college, and two summer camp communities)
• Why getting older is mostly awesome
• Who Dirtbag Rich is actually written for (and why it’s not 40/50/60-year-olds)
• His allergy to most "lifestyle" books (see: The 4-Hour Workweek) and how he's trying to do better
• The mysterious overlaps between unschooling, tiny houses, partner dance, love of wilderness, and the pursuit of dirtbag riches
• His biggest early influences: the Berkeley Student Cooperatives, Deer Crossing Camp, and Not Back to School Camp—yin and yang
• The magic of working your ass off, surrounded by people you deeply respect, in a beautiful natural environment
• How pointless school experiences led him to a deeper search for purpose, which he found in off-trail backpacking, reading alternative education theory, and independent foreign travel
• The flywheel of total aliveness, curiosity, enthusiasm, and positivity—and how keeping the flywheel going became his purpose
• What idolizing a dirtbag hiker (and failing to hike the Pacific Crest Trail) taught him at age 22
• His money situation
• How his life is currently not working

And finally, if you stick around to the very end: Jenny & Blake’s illicit scheme to create a "dark night of the dirtbag soul" OnlyFans.

Full transcript: dirtbagrich.com/blake