Dirtbag Rich

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...

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...

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...

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 ke...

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 h...

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...

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 expl...

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...

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 unle...

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 jo...

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 trans...

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...

Victoria Bruce is a 39-year-old writer, adventurer, and single mom who hiked New Zealand’s 3,000-kilometer Te Araroa trail with her seven-year-old daughter, Emilie. ( @adventures_with_emilie ) Victoria’s journey stemmed from a desperate need to escape the crushing stress of city life and heal from complex post-traumatic stress disorder, a legacy of her difficult childhood. Through six months of hi...

Alastair Humphreys is a 47-year-old British adventurer, author, and speaker who has cycled around the world, rowed across the Atlantic, busked with a violin across Spain, and made a career from telling his stories and encouraging others to live more adventurously ( alastairhumphreys.com ). Alastair talks about the “push” and “pull” factors that drive certain people toward lives of wanderlust and a...

Russell Max Simon is a 42-year-old climber, marketer, and “post-nomad” who splits his time between a derelict house in Spain and an old farmhouse in New Hampshire. ( russellmaxsimon.com ) After living many years as a digital nomad, Russell settled down in New Hampshire during the pandemic and rediscovered the virtues of place and community. Now he owns (and constantly renovates) two old properties...

Kelsey Shipman is a 39-year-old writer, mom, former teacher, and ambivalent expat living in San Miguel de Allende, Mexico, while escaping the heat, politics, and high cost of her home state of Texas. ( kelseyshipman.com / @kelseyerinshipman) Kelsey is the weirdo world traveler from an otherwise conventional Texas family who ended up living in Ghana, Bolivia, the Czech Republic, and Uzbekistan over...

Suzanne Roberts is a 54-year-old travel writer, memoirist, educator, and lifelong ski bum. ( suzanneroberts.net ) Ever since quitting her full-time job at 47, Suzanne Roberts has written books, published poetry, traveled the world, and skied every winter while living off a modest income with her semi-retired husband. We discuss Suzanne’s decision to not have kids, growing up with a family traditio...

Hannah Bowley is a 32-year-old speech-language pathologist in Seattle who recently cycled across the world for a year and plans to do something similar every three years. ( @hannahbowley ) Hannah and I met when she hosted me, as a total stranger, at her apartment in Seattle. We later embarked upon a 5-week cycle adventure in Patagonia , where we experienced stunning landscapes, challenging gravel...

Brendan Leonard is a 45-year-old writer, illustrator, ultramarathon runner, new father, and former dirtbag who makes a living by sharing his love for the outdoors. ( semi-rad.com / @semi_rad ) After spending many years focused on running, climbing, skiing, cycling, hiking, and traveling, Brendan Leonard has settled down in Montana with his wife and young son. He explains the original meaning of th...

Brittany Goris is a 31-year-old nomad who lives in her van, works 15 hours a week doing graphic design, and spends the rest of her time as a professional rock climber. ( brittanygoris.com / @gorisb) We discuss what Brittany learned from witnessing bankruptcy as a child, the guilt she feels when eating at restaurants, how her life truly began when she moved into her car, and the deep sense of belon...

What's this podcast about? What's a dirtbag, and what does it mean to be dirtbag rich? Who will you hear from, and what will we discuss? And if you followed me here from the alternative education world—what's the connection? So many questions, and so many answers. Welcome to Dirtbag Rich. Video & transcript: dirtbagrich.com/intro