Dirtbag Rich

• Jonathan Kalan: photojournalist, founder, startup consultant

  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

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• Halle Homel: climber, guide, nomad

  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

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• Daphné Robichaud: travel guide

  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

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• Jenny Abegg: writer, runner, mountain goat

  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

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• 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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