Zero To Travel Podcast

This week, I'm sharing a bonus episode from a brand new podcast called Y We Travel, co-hosted by my friend Eric Weiner, who has joined me on the show a few times over the years. Eric is a New York Times bestselling author and former foreign correspondent, and his co-host Erica Vella is an award-winning podcaster and former broadcast journalist. 

There's no shortage of travel advice out there — who can save us a buck, what to do, when's the best time to go, where to go. But one fundamental question often gets left behind: why? 

Born from an award-winning magazine series of the same name, Y We Travel explores the deeper motivations behind our journeys. The show unpacks the emotions, discoveries, and purpose that give travel its meaning. 

In this episode, Eric and Erica discuss the origins of the series and their own motivations for travelling. Eric interviews author and Y We Travel essayist Pico Iyer, trading travel anecdotes from Japan to California to North Korea and discussing themes from Pico's piece in The Walrus magazine, which argued that we should travel to meet our neighbours. Erica continues the conversation with a selection of Toronto Pearson passengers, asking: "Why are you travelling today?" 

Resources: 


Sign up for the Zero to Travel FREE newsletter 


Listen to Y We Travel on Apple, Spotify 


Read the companion essays at ywetravelmag.ca 


Contact Y We Travel: hello@ywetravelmag.ca 


Learn more about Pico Iyer 

Want More?: 


The Geography of Bliss With Eric Weiner 


How To Live a Long and Useful Life (The Wisdom of Ben Franklin) With Eric Weiner 


Rick Steves On the Hippie Trail (The Making of a Travel Writer) with Special Guest Host Eric Weiner 

Thanks To Our Sponsors: 


Become a Fora Advisor today at foratravel.com/zerototravel 


Check out Morning Brew Daily for business news that's actually fun. 

Learn more about your ad choices. Visit megaphone.fm/adchoices

Matt Gray is the founder and CEO of Pangea, a free social travel app built to help people coordinate travel plans, share recommendations, and connect with their network around the world. After a decade in product development and corporate M&A at a global fintech company, he left the corporate world in 2023 to become a full-time digital nomad and build Pangea full-time. He is on a personal mission to visit every country in the world.

In this episode, we get into seven travel tech trends shaping how people plan, book, and experience travel, including why most travel apps fail, the rise of social travel, and what AI can and can't do for travelers right now. We also dig into destination recommendations, advice for running a remote business on the road, and what it means to bridge the nomad bubble.

These are genuinely fascinating times to be a traveler and a builder in the travel space, and Matt sits at the center of both worlds. He's thinking seriously about why travel tech has such a high failure rate, and what it would actually take to crack the code, and he brings a perspective that is grounded in years of on-the-ground experience across dozens of countries and travel styles. There is a real conversation here about the gap between wanting to travel and actually doing it, and I think it will stick with you. The travel tech trends for digital nomads piece is insightful, but the human thread running through it all is what makes this one worth your time.

Have you ever had a piece of technology genuinely change how you travel or connect with people on the road? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.

Tune In To Learn:

Why so many travel apps are built to solve a single problem, and why that almost always leads to failure

How being a "multifaceted traveler" is reshaping what a useful travel platform actually needs to do

Why AI wrappers on ChatGPT are not the same as AI-powered travel tools, and how to tell the difference

How social travel is changing the reason people book trips in the first place

Why off-the-beaten-path destinations benefit most from the rise of connected travel communities

How to break out of the nomad bubble and go deeper in the places you visit

Why the people you travel with may matter more than the places you go

Destination recommendations for regions quietly gaining traction in the nomad world

Advice for running a remote team while living a location-independent life

What it looks like to bring urgency to travel, not just talk about it

And so much more

Resources:

Sign up for our FREE newsletter

Download the Pangea app

Pangea on Instagram

Couchsurfing

Workaway

Want More?

From Expat to Digital Nomad: Finding Your Travel Rhythm, Balancing Burnout, and the Digital Nomad Lifestyle with Kristin Wilson

The World's Most Traveled Person on the Ethics of Gamifying Travel, Best Regions in the World, and Why To Keep Traveling With Harry Mitsidis of NomadMania

Top 5 Reasons For "Slomading" + The Benefits Of Boredom With Tim Marting From Citizen Remote

Thanks To Our Sponsors

Become a Fora Advisor today at foratravel.com/zerototravel

Check out Morning Brew Daily for business news that's actually fun.

Learn more about your ad choices. Visit megaphone.fm/adchoices

What would it mean to stop measuring your life by the conventional yardstick and start building one that actually fits? 

Blake Boles is a writer, experiential educator, and the founder of Unschool Adventures, a travel company for self-directed teenagers, which he has run since 2008. He is the author of several books on alternative education and self-directed learning, and his newest book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, was released in March 2026.  

In this episode, Blake and I get into the philosophy behind "dirtbag rich" living, including what it really means to pursue a high-freedom, low-income lifestyle while still navigating the demands of modern capitalism. We also dig into the practical side of how to make a non-traditional financial model actually work, and talk about purpose, downward mobility, unschooling, outdoor adventure, and so much more. 

If you've ever wondered whether there's a middle path between grinding toward a distant retirement and going full dirtbag with no financial safety net, this conversation is going to give you a lot to think about. Blake shares a lot of real practical substance in this one, alongside some genuinely fresh thinking about how to measure wealth, what freedom actually requires, and what gets in the way of most people finding their version of a dirtbag-rich unconventional life. 

What does "enough" look like for you, whether that's money, time, adventure, or something else? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

Tune In To Learn: 


Why the original dirtbag culture offers a useful framework, even if you'll never live in Yosemite full-time 


How Blake figured out a way to earn good money in short bursts and stay free the rest of the year 


Why "how do you know when you're wealthy?" is a more useful question than you might expect 


What the FIRE movement often gets wrong about making a clean break from work 


How to think about "downward mobility" as a feature rather than a failure 


Why having freedom from something isn't enough without also knowing what you're free to do 


What the real risks of a dirtbag rich lifestyle actually are, and how to go in with clear eyes 


How purpose shows up differently for different people, and why measuring it in "I get to" days works 


Advice for attracting the ideal clients and building work that doesn't eat your life 


Why getting your ideal client to feel genuinely excited to work with you is the job before the job 


And so much more 

Resources: 


Sign up for our FREE newsletter 


Blake’s website 


Dirtbag Rich book 


Unschool Adventures 

Want More? 


The Vagabond's Way: Meditations on Wanderlust, Discovery, and the Art of Travel w/ Rolf Potts  


The 5 Best Hacks of “All the Hacks”: Travel, Money & Life Optimization with Chris Hutchins 


Digital Detox: Downsizing Your Digital Life to Create Freedom + Reboot Your Lifestyle Business with Corbett Barr 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Check out Morning Brew Daily for business news that's actually fun. 

Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever considered traveling to or working from Uruguay? 

Lucia Krygier is a Uruguayan entrepreneur and innovation consultant based in Montevideo. In early 2025, she spent two months working remotely from Cape Town, South Africa, an experience she describes as a turning point in her life. That trip led her to found Work From Uruguay, a community-driven workation program bringing together remote workers, digital nomads, and entrepreneurs to co-live and co-work in Uruguay. 

In this episode, Lucia shares her journey from first-time remote worker to budding business owner, and makes a strong case for why Uruguay deserves a spot on your radar. 

There is something worth sitting with in this conversation about what happens when you stop waiting for the right moment and just go. Lucia's path touches on trusting yourself through uncertainty, building a life around how you actually want to live, and what travel to Uruguay's hidden gems can unlock when you give a place more than a few days.  

If you had the chance to spend a few months working and traveling somewhere completely new,  would you take it? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

Tune In To Learn: 


Why Lucia's first remote work trip to Cape Town changed the direction of her life 


How she decided between constantly moving and staying in one place for an extended time 


The hidden costs and benefits of spending more time in one place instead of country hopping 


The mindset shift that helped her leave a stable job and launch a business from abroad 


How she handled the uncertainty of starting a consulting career while traveling across Europe 


Why she built her business around her home country instead of continuing to travel indefinitely 


What Uruguay's digital nomad permit is and how it works for long-term visitors 


The off-grid beach village that gets a "wow effect" from every single visitor who goes there 


Seven specific places in Uruguay worth visiting, from a colonial port town to a bohemian surf village 


What to eat in Uruguay, from the national sandwich to a dish tracing back to Italian immigrants 


Advice for testing the work-travel lifestyle before committing to a full nomadic year 


And so much more 

Resources: 


Sign up for our FREE newsletter 


Work From Uruguay 


Instagram 

Want More? 


Building a Travel Lifestyle: Digital Nomadism, Slow Travel, Exploring Latin America with Kyle Cohenour 


From Expat to Digital Nomad: Finding Your Travel Rhythm, Balancing Burnout, and the Digital Nomad Lifestyle with Kristin Wilson 


Creating A Life Abroad + Expert Remote Work Advice with Chase Warrington 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Check out Morning Brew Daily for business news that's actually fun. 

Learn more about your ad choices. Visit megaphone.fm/adchoices

What do you do when the adventure ends? 

Tom Turcich is a motivational speaker, author, and the tenth person in history to walk around the world. Over seven years, he and his dog, Savannah, covered 28,000 miles across 38 countries and six continents, completing the journey in 2022. He is the author of the memoir The World Walk and the children's book Savannah's World of Adventure. 

In this episode, Tom shares what returning home after long-term travel actually looks like, from the mental and emotional toll of losing the road, to the financial catch-up game, to the harder question of who you are once the adventure is over. 

If you've ever come back from a trip and felt a strange kind of grief you couldn't quite name, this one is for you. Tom is remarkably open about the difficulty of that first year back, and the conversation gets into territory that doesn't often get talked about after a big journey ends. There's real honesty here about what it takes to find your footing again, how to rebuild adventure into a life that isn't handing it to you every day, and how to make peace with the constraints that come with settling down. 

What's one thing you've held onto from a big trip that's hard to explain to people who weren't there? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

Tune In To Learn: 


Why Tom describes his first year back as the only depression he's ever experienced 


How the world "stops coming at you" when you settle down, and what it takes to rebuild that muscle 


The unexpected mental and emotional challenge of no longer having a North Star 


Why consistency beats passion when it comes to making progress, in travel and in life 


What two years of walking in the Atacama Desert taught Tom about happiness 


Why your traveler identity matters less than the values underneath it 


How walking became a years-long meditation practice Tom didn't see coming 


The one mindset Tom would give anyone coming off the road for the first time 


Why building community after a big adventure takes longer than most people expect 


What it means to choose your constraints rather than just accept them 


And so much more 

Resources: 


Sign up for our FREE newsletter 


Tom’s website 


The World Walk book 


Microadventures book 

Want More? 


Walking the World with Alexander Campbell and Tom Turcich 


The World Walk (Trilogy): Lessons From A 7 Year Walk Around The World w/ Tom Turcich 


Exploring A Single Map: A Travel Adventure For Everyone With Alastair Humphreys 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Check out Morning Brew Daily for business news that's actually fun. 

Learn more about your ad choices. Visit megaphone.fm/adchoices