Dirtbag Rich

About Dirtbag Rich

How do you build a life of freedom, travel, nature, and meaningful work? Join author Blake Boles (blakeboles.com (https://blakeboles.com)) as he dives deep with working adults who have managed to strike that elusive balance of time, money, and purpose—without giving up on their wildest dreams. These vulnerable and provocative conversations reveal how everyday people create lives filled with wilderness adventure, creative expression, frequent exploration, and financial stability—no trust fund required. Each guest shares their unique flavor of "dirtbag rich": a way of living that prioritizes time wealth, personal relationships, and transformative experiences over luxury, comfort, and excess security. ("Dirtbag" is a badge of honor in climbing and hiking communities, describing someone so devoted to their passion that they trade conventional success for the chance to do what they love, full-time.) Visit dirtbagrich.com (https://dirtbagrich.com) for full transcripts and updates on Blake's forthcoming book, Dirtbag Rich: Low Income, High Freedom, Deep Purpose.

Publisher

Blake Boles

Category

education · society & culture

Language

en

Explicit

No

First episode

1 Nov 2024

Latest episode

4 Oct 2026

Latest episodes

50 episodes in the feed.

1. 

   4 Oct 2026

   Mila La Haye: climber, dancer, traveler, guide

   Amelia “Mila” La Haye is a 29-year-old mountain guide-in-training, climber, dancer, and longtime dirtbag who has spent the past decade building a life around curiosity, connection, and very little money. At 19, she left Quebec for British Columbia with a hammock and climbing gear, and since then she’s lived in a car, joined a squat in Melbourne, studied dance, performed with a physical theater company, and traveled and worked her way around the world. (@m.i.l.a__s.o.l_ (https://www.instagram.com/m.i.l.a__s.o.l_/)) Mila tells the story of dumpster diving and relying on strangers during a three-month, nearly zero-dollar bicycle trip across Europe with a friend, learning firsthand how much generosity exists when you simply ask. But that trip was just one chapter in a much bigger decade of experimentation: circus in California and Australia, workaways, vanlife, acroyoga, “trance dance” in Indonesia, Waldorf education, and eventually two years of adventure studies in Canada on the long road toward becoming an internationally certified mountain guide. She has supported this lifestyle through seasonal jobs including tree planting, moving, gardening, wildfire work, and geotechnical fieldwork, often working only three or four months a year. She also has a financial cushion from childhood that gives her some psychological security, while keeping her expenses low and cultivating deep relationships has allowed her to live on remarkably little. Her recent geotechnical work even came through a chain of friends vouching for one another, illustrating just how much her life depends on community rather than conventional career ladders. We talk about growing up in an adventurous family where treasure hunts, messy play, curiosity, and ridiculous family music videos were all part of normal life and how she found both the creative possibilities and cultural limitations of formal dance school. She also wrestles with the contradictions of working in the mining industry while caring deeply about the environment, and with the tension between her current “Mountain Mila” life of climbing and guide training and her desire for a home base, stability, and somewhere to keep her stuff. Mila’s life is less a single grand adventure than a decade-long experiment in following curiosity, choosing connection, and repeatedly asking what makes her feel most alive. Her next chapter involves mountain-guide exams, ice climbing, skiing, another winter in Chile, and a 30th-birthday “celebration of life” in Squamish. The future remains pleasingly unclear. Full transcript: dirtbagrich.com/mila (https://dirtbagrich.com/mila)

2. 

   13 Sept 2026

   Daniel Greenberg: nomadic community builder

   Daniel Greenberg is a 62-year-old community builder, serial social entrepreneur, and long-time nomad who has spent more than half his life in intentional communities and lives on less than $24,000 a year. (daniel@ic.org) Daniel traces his unconventional path from graduate research on children growing up in communes to traveling around the country in a Westphalia camper van, living in communities around the world, and starting organizations that introduce people to alternative ways of living. He explains why most people don’t even think to put “community” on their list of things they want from life, the differences between communes, co-housing, and ecovillages, and why he sees these communities as laboratories for figuring out how humans can live well and lightly together. Today, Daniel bounces between communities in Massachusetts, Scotland, India, and Brazil, carrying almost everything he owns in a backpack and carry-on. He has about $8,000 in the bank, owns a house that doesn’t generate income for him, and somehow manages to put a daughter through college. Daniel describes why planning too far ahead can actually make his life worse, how he thinks about his extraordinary network of friends as a form of wealth, and the messy realities of living alongside other people, from incompatible kitchen standards to the challenge of “cohesion without coercion.” Finally, Daniel reflects on why he’s never been particularly interested in maximizing his salary and why his guiding question isn’t “Where should I go next?” but “Where do I need to be, who do I need to be with, and where can I contribute?” Full transcript: dirtbagrich.com/daniel (https://dirtbagrich.com/daniel)

3. 

   30 Aug 2026

   Tim Voors: long-distance hiker, writer, advertiser

   Tim Voors is a 53-year-old Dutch writer, artist, former advertising executive, father of three, and long-distance hiker who discovered a sense of belonging among a worldwide community of “happy misfits.” (timvoors.nl (http://timvoors.nl/)/@timvoors (https://www.instagram.com/TimVoors/)) After 20 years of working with brands like Heineken, Booking.com, and Budweiser, Tim began thru-hiking in his forties, searching for the fear, humility, and adrenaline that corporate success could no longer provide. His adventures have since taken him across the Pacific Crest Trail, Continental Divide Trail, Te Araroa in New Zealand, multiple Caminos, and Japan’s 1,200-year-old 88 Temples pilgrimage, where he slept on cardboard in bus stops alongside elderly Japanese hikers. We get into Tim’s 10-year experiment to build income streams that would allow him to earn money while preserving the freedom necessary to frequently take long hikes. The result is a patchwork of books, speaking, art, clothing, workshops, and two Airbnb units that satisfies both his financial needs and his human need to feel useful. Tim also describes the joys of teaching painting and singing from home while wearing Crocs and Hawaiian shirts, makes the case for doing many things instead of becoming a specialist, and explains why he now feels more like a pilgrim than a backpacker. Full transcript: dirtbagrich.com/tim (https://dirtbagrich.com/tim)

Who has been a guest on Dirtbag Rich

Names identified in recent episode analyses. Showing up to five guests.

• Michael Hughes
• Jack Schott
• Morgan Sjogren
• Blake Boles
• me

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

7 ratings

Spotify

4.9 / 5

23 ratings

Podcast Authority Score: 20 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

28

Social presence

0

YouTube

0

Engagement

32

Shows with a similar audience

• 

  Hidden Brain

• 

  The Dirtbag Diaries

• 

  Ageless Athlete

• 

  Two Sides of FI

• 

  Ten Percent Happier with Dan Harris

• 

  MoneyWatch with Jill Schlesinger