301: Visiting Every Country in Central & South America and How Not to Cross the Venezuelan Border with Ashley Company

301: Visiting Every Country in Central & South America and How Not to Cross the Venezuelan Border with Ashley Company

Author: Matt Bowles: Full-Time World Traveler Since 2013 September 9, 2024 Duration: 48:41
Learn how immersive trips to the Dominican Republic, Kenya and backpacking through South America can be life-changing. ============================ Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds. ============================ ON THIS EPISODE Ashley Company starts off by talking about her experiences traveling the world for wine, and why the South African wine region is so unique and special.  She then talks about her experience growing up in the U.S., traveling to Turkey as a kid, living in South Korea for a year at age 12, and attending an HBUC for college. She then describes how her first solo trip to the Dominican Republic was completely transformative, as was her first trip to Kenya. Ashley then explains what led her to quit her job and backpack through every country in South and Central America. She shares stories about traveling to San Basilio de Palenque in Colombia and accidentally entering Venezuela without going through immigration. Ashley also talks about the power of her first experience attending Carnival in Trinidad and why she has been back 10 times since. And, finally, she reflects on the impact that a full year of backpacking in South America had on her as a person, and how it shaped her life and entrepreneurial trajectory. ⁠ ⁠ → Full show notes with direct links to everything discussed are available here. ============================ FREE RESOURCES FOR YOU: See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual) Watch my Video Training on Stylish Minimalist Packing so you can join #TeamCarryOn See the Travel Gear I Use and Recommend See How I Produce The Maverick Show Podcast (The equipment, services & vendors I use) ============================ ENJOYING THE SHOW? Follow The Maverick Show on Instagram and DM Matt to continue the conversation Please leave a rating and review — it really helps the show and I read each one personally You can buy me a coffee — espressos help me produce significantly better podcast episodes! :)

There’s a certain texture to life lived in motion, a collection of stories that emerge not from postcards but from the messy, beautiful reality of planting roots in foreign soil. The Maverick Show: Global Travel Stories & Life Beyond Borders captures that essence through long-form conversations hosted by Matt Bowles, who has been navigating the world full-time since 2013. This isn't a guidebook podcast; it’s a series of intimate dialogues, often unfolding casually over a shared bottle of wine, where the destination is understanding. You’ll hear from a diverse range of voices-expats, digital nomads, women forging paths abroad, and diaspora storytellers-each sharing the raw, unfiltered nuances of what happens when you cross borders for good. The focus is on the human narrative beneath the itinerary: the cultural misunderstandings that become breakthroughs, the loneliness and liberation, and the profound ways a global life reshapes identity. Listening feels like pulling up a chair at a cafe somewhere in the world, eavesdropping on a conversation that’s equally about internal discovery as it is about geographic change. Matt’s own experience as a long-term traveler informs these discussions, steering them toward the substantive lessons learned far from home. If you’ve ever wondered about the true weight and wonder of building a life between cultures, this podcast offers a genuine, thoughtful window into that journey.
Author: Language: English Episodes: 100

The Maverick Show: Global Travel Stories & Life Beyond Borders
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