Dirtbag Rich

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, a flight attendant for Delta and an unschooling mom, shares her journey from aspiring lawyer to airline professional. She digs into the hidden economics of flight attending, revealing how to optimize schedules for family needs. Julieta candidly discusses their financial history, balancing a tight budget, and embracing minimalism with the motto, "spend less, don’t work more." Her transformation to unschooling has reshaped her parenting style and perspective on time. Plus, she highlights her love for bookstores and the beauty of Michigan's nature.

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

In this engaging conversation, Blake Boles, a writer and traveler known for leading self-directed adventures for teens, shares his journey and philosophy on freedom, purpose, and security. He discusses his love for minimalism and owning less, while emphasizing the importance of human connections formed through dance and travel. Blake critiques conventional lifestyle literature and reflects on his own influences from alternative communities. The duo also explores the transformative power of unschooling and wilderness experiences, highlighting the challenges and joys of a non-traditional path.

The host reflects on the balance between time, money, and purpose, all through the lens of outdoor adventures. Excitement bubbles over as they share updates on both the podcast and an upcoming book. Listeners are encouraged to suggest diverse guests to inspire richer conversations. It's all about embracing a lifestyle that values exploration and meaningful experiences!

Kaya Lindsay is a 32-year-old climber, filmmaker, vanlife veteran, and accidental gym owner in Moab, Utah. (onechicktravels.com / @onechicktravels)In her early twenties, Kaya fell in love with bouldering at a Santa Cruz gym, met a tattooed vegan woman with a Sprinter van, and realized she could climb full-time. She built out a van, hit the road, and spent four years chasing perfect weather and fleeting friendships from Bishop to Squamish to Indian Creek. Along the way, she hustled together a dirtbag media career: filming, blogging, scoring gear deals, and slowly building a name with her One Chick Travels YouTube series, which spotlighted the unseen women shaping the climbing world.Kaya talks about living on $1,000 a month, the hidden privilege of trust fund dirtbags, and the unspoken rules of social capital in the outdoor scene. She describes what finally pushed her off the road: constant vigilance, repeating the same small talk, and never knowing if her community would stick around when the rain came. Kaya also describes why settling down in Moab felt like upgrading to a bigger container, not a smaller one.We get into how a base jumper literally fell out of the sky and became her business partner, what it’s like running Moab’s first climbing gym, and how building a rooted, weather-independent community has changed her life. Kaya also opens up about the neurodivergent undertones of dirtbag culture, the bittersweet question of what happens to aging climbers, and how it feels to finally walk into the grocery store and see someone who knows your name.Full transcript: dirtbagrich.com/kaya