Dirtbag Rich

Tracy and Andy Duncan are a couple living full-time aboard Another Summer, a boat they call home with their five children. (linktr.ee/SVanothersummer)Leaving behind suburban life in Atlanta, the Duncan family embraced a life of adventure, spending their days on the open water and learning to balance work, family, and self-sufficiency. Tracy shares how COVID pushed them to rethink their lifestyle, how their time together during the lockdown led to a deeper connection and a desire for more freedom, and how homeschooling was a natural fit for their children, particularly those with special needs.Living on a boat has its own set of challenges, from organizing a floating home with limited storage to managing basic repairs in a remote location. Andy and Tracy reflect on how their lives have become more organized than ever, driven by the necessity of dealing with the logistics of boat life—whether it’s finding the right part for a repair or packing food in small spaces. Their financial setup is unconventional, relying on adoption stipends for day-to-day expenses, while Andy’s remote IT work supports big-ticket items like boat repairs and upgrades.The Duncan family has found an unexpected rhythm in their nomadic life, with their children thriving in an environment where they have constant access to each other and the natural world (complete with “roving pirate gangs” of teenagers). Tracy talks about how their kids have formed tight-knit relationships not only with each other but also with the broader boat community, which is a small, interconnected world of its own. Andy and Tracy also share how they balance the close quarters of boat life with the need for individual space and reflection, and how their family’s adventures continue to shape their values and sense of connection.Full transcript: dirtbagrich.com/tracyandandy

Jonathan Kalan is a 37-year-old photojournalist-turned-entrepreneur who built his career reporting from the front lines of revolutions, refugee crises, and emerging tech scenes across Africa and the Middle East. (jonathankalan.com)Publishing in outlets like The New York Times and The Atlantic, he covered the sharp edges of globalization—until the stress, financial instability, and nonstop travel burned him out. Tired of chasing deadlines and scraping by on freelance checks, he walked away from journalism without a clear plan, except that he wanted more control over his life.That decision led to Unsettled, a company offering travel experiences designed for professionals who weren’t ready to settle into a single career, city, or routine. Jonathan describes the chaotic early days of launching the business—testing ideas in borrowed villas, running trips on razor-thin margins, and figuring out how to sell something as intangible as “structured uncertainty.” The demand was immediate, and Unsettled quickly expanded to destinations across Latin America, Europe, and Southeast Asia, attracting mid-career professionals looking for something between a vacation and a career change.But growth didn’t mean stability. Jonathan talks about the financial rollercoaster of running a business dependent on global travel, how the pandemic nearly destroyed everything overnight, and the brutal decisions he and his co-founder had to make to keep Unsettled alive. He breaks down the economics of the business—why they never took venture capital, how they priced trips to be profitable but accessible, and what it took to rebuild after their revenue went to zero in 2020.These days, Jonathan works as a startup consultant, helping founders navigate early-stage growth, branding, and business strategy. He shares how his experience building Unsettled shaped his approach to entrepreneurship, why he’s skeptical of venture-backed business models, and the biggest mistakes he sees new founders make. We also get into the time he nearly bought a failing surf lodge in Nicaragua, the strangest place he’s ever worked from, why "hustle culture is bullshit," and our shared experience of cycling the Carretera Austral in Patagonia.Full transcript: dirtbagrich.com/jonathan

Halle Homel is a 27-year-old outdoor guide, van dweller, and questioning nomad who built her life around travel, adventure, and seasonal work—and now asks herself whether the road still feels like home. (@halletreks)After graduating college a year early with a degree in creative writing, Halle hit the road in her Kia Soul and spent three months visiting all 48 contiguous states alone. That trip turned into six years of van life, guiding rock climbing, backpacking, and canoeing trips across the U.S. while living on public land and making seasonal wages stretch through the winter. But as she and her partner juggle life in a van with a six-day-a-week climbing schedule, the absence of a real home base is starting to feel more like survival mode than freedom.We discuss the economics of seasonal guiding: how she makes $200 a day on average, relies on tips for daily expenses, and stretches her summer paychecks to last all year. Halle shares the reality of van life in 2024, from Walmart parking lots to the mental toll of constantly moving, and why she’s now searching for a mountain town where she can return year after year. She also talks about breaking into the guiding world as a woman, the sexism she’s faced in climbing, and how she’s using her new Single Pitch Instructor certification to carve out a long-term career in outdoor leadership.She opens up about her evolving relationship with social media after going viral on TikTok, her role in environmental advocacy, and the tension between craving stability and chasing big, audacious goals—like summiting all 15 of California’s 14,000-foot peaks before October.Full transcript: dirtbagrich.com/halle

Daphné Robichaud is a 32-year-old outdoor travel leader who makes her living guiding hiking and biking trips across the world. (@thewanderingdaph)Daphné spends her summers leading back-to-back adventures in places like Patagonia, Iceland, and the French Alps: solving problems on the fly, adapting to new groups every week, and spending long days on trail. We talk about what it’s like to build a life around seasonal work, the thrill and exhaustion of constantly resetting with new teams, and how she structures her year to maximize both income and time off.Daphné breaks down the financial realities of trip leading: why she saves nearly 40% of her earnings despite an unpredictable schedule, how free housing and food change the equation, and why she feels more financially stable now than she did working a salaried government job.Earlier in her life, Daphné studied criminology and international development, struggled with anxiety throughout her 20s, and deeply questioned whether she was on the right path. Now she doesn’t worry about what comes next—just whether her next winter will be spent in the mountains or by the sea. Despite the constant movement, she’s found ways to maintain deep friendships and a committed relationship, proving that stability doesn’t have to come from staying in one place.Full transcript: dirtbagrich.com/daphne

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