Zero To Travel Podcast

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

What does it actually take to give yourself permission to live unconventionally, and what's really standing in the way?  I had the opportunity to be a guest on the My Most Authentic Life podcast with Fede Vargas, a conversation we recorded live on the rooftop at Podcast Movement Evolutions during South by Southwest in Austin, Texas. Fede interviewed me about the themes that run through this show, including unconventional paths, pivots, lifestyle design, and what it means to choose differently.  This conversation pulls out some of my most honest thinking on what it means to give yourself permission to live unconventionally. We talk openly about my decade as a nomad with no fixed home, the internal and external forces that push back against unconventional choices, and how imposter syndrome never goes away but can be trained around. There's a lot here that I think will resonate if you've ever felt the pull of a different path but weren't sure you were allowed to take it.  Tune In To Learn:  Why giving yourself permission is often the first and hardest obstacle on any unconventional path  How imposter syndrome works as a muscle you can train, not a problem you solve  What it means to "pivot" before you've actually made any outward moves  Why the journey before the journey has more value than most people realize  How lifestyle design is less about optimization and more about filtering decisions through your ideal daily life  Why the "perfect average day" exercise is a practical starting point for anyone designing their life  How I spent a decade as a nomadic tour manager, including driving the Meow Mix Catmobile across the U.S.  What unexpected things can happen when you follow your gut, even last-minute  Why my definition of authenticity comes down to one word  And so much more  Resources:  Sign up for our FREE newsletter  My Most Authentic Life  Instagram  The Perfect Average Day  Laundry House  Want More?  How to Pivot to a Life With More Freedom (And Travel), Get More Free Time, and Unlock Your Intuition With Jenny Blake  How to Navigate Transitions and Design Your Life (Without the BS) with Lauren Handel Zander  Two Paths to Location Independence and Travel (No Skills Required) With Caitlin Sunderland and Janessa Klatt  Thanks To Our Sponsors  Become a Fora Advisor today at foratravel.com/zerototravel  Get 20% of at Cozy Earth with code ‘TRAVEL’  Learn more about your ad choices. Visit megaphone.fm/adchoices