Dirtbag Rich

Jenny Abegg is a 40-year-old mountain athlete, writer, and business co-founder who has built her life around spending extended time in the mountains. (@jabegg)Jenny describes how she went from a religious upbringing that emphasized self-denial and sacrifice to a life fully dedicated to climbing. She recalls the moment she left the church, the deep personal transformation that followed, and how moving into her van and chasing vertical adventure became her form of self-discovery.We discuss her evolution from mountaineering, to climbing, to her current obsession: long, technical mountain linkups in running shoes, where she combines her climbing background with ultra-distance endurance. Jenny reflects on why she’s more anxious in everyday life than when she's committing to an alpine traverse, the feeling of absolute freedom that comes from moving fast in the mountains, and what it’s like to be the "crazy lady in running shoes" on a glacier.We also get into the financial side of her dirtbag years—living in a van, earning just enough as a freelance writer and guide, and later using smart real estate moves to build long-term security. Jenny now co-runs BetterTrail, an outdoor gear review site that blends sustainability with practical advice.Finally, Jenny opens up about turning 40, grappling with the question of long-term purpose, and wondering what life will look like when her body no longer lets her run across the mountains she loves.Full transcript: dirtbagrich.com/jenny

Ed Gillis is a 49-year-old teacher, writer, and bike tourist who, along with his 44-year-old wife Jocelyn, has spent the last 16 years enjoying long cycle trips with their two sons. (yukon4explore.com)From hiking Patagonia with a newborn to biking 10,000 kilometers across Europe as a family of four, Ed breaks down how they made adventure a non-negotiable part of parenting. He shares how they kept the trips affordable—living without a car, cobbling together gear, and taking full advantage of the generosity of strangers. We discuss the financial trade-offs of choosing time over money, the long nights spent juggling freelance work and childcare, and how their Yukon-based careers as a teacher and naturopath allow them to take summers (and sometimes half-years) off for extended bike tours.Now that their teenage sons plan the routes and carry most of the gear, Ed jokes that his days of being the strongest rider are over. We also get into the magic of Warmshowers hosts, why New Zealanders love inviting traveling families into their homes, and what happens when your only roadtrip soundtrack is One Direction.Ed’s books, Bike Touring with Kids: the Oceania Odyssey and Bike Touring with Kids: the Europe Epic, document the family’s adventures.Full transcript: dirtbagrich.com/ed

Artec Durham is a 39-year-old ICU nurse, property investor, and former dirtbag who only works two shifts a month—and still manages to cover his living expenses through strategic real estate choices. (@artec_rn)Artec shares his unconventional path, from a childhood spent unschooling, guiding wilderness trips, and discovering a passion for nursing through wilderness medicine. He breaks down how he buys fixer-uppers and turns them into rental income, with YouTube as a teacher. Today he maintains his properties with just a few days of work each year, spends his summers hosting outdoor athletes at his Colorado property, and uses his time for adventures like bikepacking across Death Valley and packrafting the Grand Canyon. His primary vehicle is a totaled minivan, which he uses to retrieve abandoned building supplies from the side of the road.We discuss the thrill and toll of ICU nursing, why Artec never wants full-time employment again, and how his dirtbag upbringing led to a lifelong commitment to maximizing freedom and community over traditional metrics of success. Artec also opens up about how pushing his physical limits through ultra-distance bike races led to heart complications, forcing him to reconsider intensity and refocus on connection, community, and the joy of playing outside.Full transcript: dirtbagrich.com/artec

Emily Pennington is a 37-year-old freelance writer, former Hollywood assistant, and full-time outdoor nerd who once lived in a minivan for a year to visit every U.S. national park. (@brazenbackpacker)In her 20s, Emily bounced between creative careers—first as an actress, then as a circus performer, then as a film producer’s assistant. The job paid okay, but the work felt meaningless, and after losing several friends to sudden deaths, she started questioning the whole plan. She cut her expenses, saved aggressively, and quit in 2020 to hit the road full-time.That trip, which started as an attempt to reboot her life, turned into a book (Feral) and a new career as a freelance adventure writer. But the realities of making a living as a writer are far from glamorous. Emily breaks down exactly how much she made from her Outside Magazine column and book advance, how she cobbles together an income from travel writing and gear reviews, and why she still occasionally wonders if the whole industry will collapse. Emily also discussed the burnout of monetizing your passions, the constant anxiety of freelance work, and how she preserves time for hikes that aren’t “content.”Now based in Boulder, Colorado, she’s finally settled into a routine that gives her the freedom she was looking for—working Monday to Thursday, keeping her weekends sacred, and skiing in the middle of the week whenever she wants. And because she can’t stop picking up new creative projects, she’s also fronting a folk-punk band called Trouble's Braids.Full transcript: dirtbagrich.com/emily

David Six is a 40-something-year-old software developer, Triple Crown thru-hiker, and lifelong travel addict who has spent the last two decades figuring out how to work as little as possible while hiking, biking, and exploring the world. (@walkacrossoregon)David breaks down how he built a life that lets him disappear into the wilderness for months at a time without running out of money. He explains how he went from high school drop-out to self-taught programmer, how he co-founded a ticket sales software company that now funds his adventures, and why he sometimes mails himself a laptop just to keep his business running while on trail. Unlike most thru-hikers, who treat long-distance hiking as a one-time adventure, David turned it into an ongoing way of life, balancing the need for income with his desire to spend as much time as possible moving through the world under his own power.We discuss what draws people to thru-hiking, why long hikes feel like time travel, and the transition shock that hits hard when the journey is over. David reflects on his anti-authority streak, his deep-seated resistance to full-time work, and why, despite having a near-perfect job setup, he still resents it. He also shares how he and his wife (a nurse) use travel hacking and careful planning to fund their adventures, including multiple round-the-world trips.Finally, David talks about his next big project: walking across the entire state of Oregon, from the Pacific Coast to the Idaho border, in the middle of winter.Full transcript: dirtbagrich.com/david

Adrianna Nine is a 28-year-old freelance writer, newsletter author, and desert enthusiast who once traded freedom for a high-paying corporate job—and lived to regret it. (adriannanine.com)Adrianna breaks down her escape from corporate trust and safety, where she made great money but had no time to spend it, except on gadgets and overpriced appetizers. She describes hitting rock bottom, ignoring everyone who told her writing wasn’t a real career, and slowly building a life of creative independence.Adrianna does freelance tech and science writing, as well as running a boutique copywriting agency. She averages 25 hours of work per week—leaving plenty of time for baking, gym sessions, desert conservation work, and personal writing projects, including a novel in progress. We get into financial habits that made her transition possible, the realities of self-employment, and why she feels more secure juggling multiple clients than working a single full-time job.We also discuss her deep love for the Arizona desert, the tattoos to prove it, and how a coyote made her cry in Joshua Tree. She talks about the themes of her newsletter, Creativity Under Capitalism: protecting your time, resisting the urge to monetize everything, and creating what matters.Full transcript: dirtbagrich.com/adrianna

Paul Millerd is a 39-year-old writer, ex-consultant, and advocate for ditching the default path in favor of what he calls “the pathless path.” (pmillerd.com / @p_millerd)Paul walked away from a promising corporate consulting career—think McKinsey, prestige, and six-figure salaries—to pursue a life of writing, experimenting, and global wandering. He describes how he initially struggled with unlearning his achievement-oriented mindset, why the idea of good work (work that energizes) became his guiding principle, and how his first self-published book, The Pathless Path, briefly and unexpectedly earned six figures.We discuss the philosophical basis of work and money, how to avoid the traps of both scarcity and overachievement, and how the value of exercising your freedom is limited by how others exercise their own freedom. (In other words: if you're free to hike on a sunny Wednesday afternoon, and no one's available to go with you, are you really free?)Paul and his wife have a young daughter, and they struggle to find and live near other, like-minded families. We talk about how online communities help Paul stay connected while living nomadically between Texas and Taiwan and how online self-education was invaluable to his success. We conclude with a discussion of navigating fear and uncertainty on the pathless path.Throughout the conversation, Paul stays refreshingly honest about the tensions between freedom and stability, the allure of easy money, and the ever-present temptation to fall back into old habits of achievement and validation. Energized by this conversation, I ended up talking more than usual about the tricky balance of factors that leads to a Dirtbag Rich existence. Full transcript: dirtbagrich.com/paul

Emma Hayward is a 30-year-old sailor who splits her time between an Antarctic research vessel, Rhode Island, and living on a boat that she fixed up. (@emmastoryhayward)Growing up on Cape Cod with parents who worked on boats, Emma never wanted an office job or predictable life—which is why she keeps building a life at sea, even as her friends settle down and start families.Emma describes her journey from a “schooner bum” to a dirtbag rich captain and boat owner who works 3-4 months/year to cover her costs and accumulate savings. Crucial to this journey was securing a position on a 300-foot Antarctic research vessel, where she launches scientific gear as part of climate-related projects.How do people make money with boats? Emma walks us through the options, from crewing fancy yachts (lucrative but not so purposeful) to charter day-trips (lucrative and somewhat purposeful) to outdoor education on tall ships (very purposeful but horribly paid). She touches on power and gender dynamics at sea, dealing with boredom and monotony, and the challenge of maintaining friendships and romantic partnership when spending so much time away.Emma also tells the story of her gap year (and a half) when she sailed from Hawaii to San Diego with her dad, as well as a recent voyage from Rhode Island to Ireland that ended with a week of dodging container ships amid thick fog.Full transcript: dirtbagrich.com/emma

Tim and Angel Mathis are married nurses and lapsed Christians who enjoy hiking, running, and traveling very long distances. Tim is the author of The Dirtbag's Guide to Life (timmathiswrites.com) and Angel teaches investment skills to fellow nurses (learn.nursesinvesting.com).Tim begins by sharing his feelings about me stealing the term "dirtbag rich"—which he coined in his 2019 book—and transforming it into a larger concept that emphasizes purposeful work.Tim finds his own purpose as a mental health nurse and book writer. He tells the story of losing his dad in the middle of a Pacific Crest Trail hike, the period of hedonistic dirtbag drifting that followed, and how he went from evangelical Christian, to Episcopal minister, to fully leaving the faith. He describes how ultrarunning and thru-hiking offered a quasi-religious new community, sense of belonging, and positive emotions. "Nature is my spirituality now," Tim says—and this is a "deeply American thing."We then hear from Angel—the financial brain in the marriage—who shares the story of getting laughed at by a financial advisor early in their careers. The couple ended up doing everything the advisor didn't think possible: buying a house, getting graduate degrees, making work optional after age 35, and traveling 3-6 months each year.Angel's sense of financial security comes from taking a hard look at the numbers each month, using the same method that she teaches to other nurses. As a nurse practitioner, she enjoys helping many patients in a short amount of time—just as long as she's working part-time. Raised Catholic and later baptized Protestant, Angel laughs about enjoying a diversified spiritual portfolio, even as nature-oriented rituals have replaced the religious ones (e.g., long runs on Sundays instead of church). She reflects on how easy it was to build new friendships in their thirties through long-term traveling hiking, where low time pressure allows deep relationships to blossom.Find Tim and Angel on Instagram: @dirtbagguide / @nursesinvestingforwealthFull transcript: dirtbagrich.com/timangel

Justin Riley is a 40-year-old dance teacher, wilderness junkie, and organizer of alternative-culture partner dance events. (justindance.com)Justin has spent nearly two decades designing events that blur the line between art, dance, and wilderness immersion. His festivals are more than just places to dance—they’re cultural experiments that challenge people to step outside their comfort zones and co-create something meaningful. Whether it’s a week-long floating dance party on Utah’s Green River or a countryside retreat in Spain, Justin’s spaces are deliberately messy and wildly participatory. (He’s also responsible for helping me fall in love with fusion dance in 2016.)We discuss Justin’s early years as a dirtbag wanderer living on $5,000 a year while chasing dreams as a photojournalist and political activist and the joy he finds in solving life’s problems without money. Today he earns money through a combination of event organizing, dance teaching, and converting buses and vans. When work feels so much like play, Justin observes, “I feel like my whole life is filled with free time.”Justin explains his "high risk, low consequence" design philosophy, his commitment to wilderness exploration (a vital counterbalance to his hyper-social work), and his belief that meaningful experiences don’t come from perfection but from trust, collaboration, mutual joy, and the willingness to let things break—and then building something new together.Find Justin’s next events at unboundfusion.com.Full transcript: dirtbagrich.com/justin