Dirtbag Rich

• Ed Gillis: adventure cyclist, educator, dad

  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

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• Artec Durham: nurse, bikepacker, property baron

  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

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• Emily Pennington: writer, minivanlifer, former circus performer

  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

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• David Six: thru-hiker, programmer, high school drop-out

  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

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• Adrianna Nine: writer, conservationist, corporate refugee

  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

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