In this episode of the Nearshore Cafe Podcast, Brian Samson sits down with Jen from Expatsi to explore what it really looks like to leave the U.S. and build a life abroad. From growing up in Alabama to relocating to Mérida, Mexico, Jen shares how she and her husband “nearshored themselves” by leveraging remote work, lowering their cost of living, and building a business that now helps others move overseas.

They discuss expat life in Mexico, Ecuador, and Belize, compare residency and visa options, break down the realities of healthcare and infrastructure abroad, and explain why more Americans are exploring international living in Latin America and beyond.

Jen also shares how Expatsi helps aspiring expats discover the right country, navigate the relocation process, and connect with trusted experts around the world.

Topics Covered:

• Moving abroad from the U.S.
• Cost of living in Mexico
• Remote work & expat lifestyles
• Ecuador and Belize for expats
• Residency and visa pathways
• Nearshoring yourself
• Building a business abroad
• Digital nomad & retirement trends

Sponsored by Plugg Technologies
https://www.plugg.tech

Follow The Nearshore Cafe Podcast
https://www.nearshorecafepodcast.com

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

What does it take to grow an IT staffing firm to $28M in revenue while competing against giants like Tech Systems? For Doug Firestone, the answer was found in the jungles of Costa Rica.

In this episode, Doug shares his transition from a Pennsylvania-based founder to a nearshoring pioneer. We explore the logistical and cultural "must-haves" for setting up shop in Latin America, from choosing the right free trade zones to hiring talent directly from tech hubs like IBM and Amazon. Doug also provides a candid look at his "failures," explaining why a great solution needs an even better go-to-market strategy to survive client pullbacks.

Key Takeaways:

• Why industry verticals (like Blue Cross Blue Shield) drive higher margins than technology niches.
• The "Calculus" of Nearshoring: Evaluating flight ease, education, and geopolitics.
• How to pitch nearshoring to big-name clients like Comcast.

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

How do you handle a land deal with a duffel bag of cash? Brendan Quirk, Founder of LACPA, joins Brian Samson to share the wild, "boots-on-the-ground" reality of doing business in Latin America for over two decades.

What started as a backpacking trip to Patagonia turned into a 20-year career as a financial leader and international consultant. From his early days as a CPA in Mendoza during the 2004 financial crisis to managing multi-country expansions for global firms, Brendan breaks down the logistical hurdles of nearshoring, capital controls, and scaling operations in a region where relationships are the ultimate currency.

In this episode, we sit down at the cafe to discuss:

• The 2004 Argentina Crisis: Lessons from building a business during extreme financial instability.
• The Mendoza Wine Boom: How Brendan became a Financial Director for a luxury winery.
• The "Institutional" Edge: Why Chile is often the most robust entry point for US firms.
• The Brazil Maze: Navigating the administrative complexity of the region's largest market.
• LATAM Loyalty: Why the "community" aspect of Latin American talent is a competitive advantage for tech founders.

Whether you are a CTO looking to hire LATAM engineers or a founder exploring nearshore expansion, this episode offers a masterclass in regional strategy and cultural adaptability.

Connect with Brendan Quirk:

• LinkedIn: https://www.linkedin.com/in/brendanthomasquirk/
• Website (LACPA): https://www.latinamericacpa.com/

Follow The Nearshore Cafe Podcast:

• Website: https://www.nearshorecafepodcast.com
• Linktree: https://linktr.ee/nearshorecafepodcast

Sponsored by Plugg Technologies: Connecting U.S. companies with vetted software engineers and digital talent across Latin America.

• Visit: https://www.plugg.tech

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

In this episode of the Nearshore Cafe Podcast, hosted by Brian Samson, we sit down with Oleg Baranov, Founder & CEO of FlameTree AI, to break down how AI agents actually work in real-world business environments.

Oleg shares why AI should be treated like a junior team member—not a finished product—and how continuous training, iteration, and feedback are essential to unlocking real value.

They also explore how companies can combine AI with nearshore talent to build scalable, high-performing teams across Latin America.

In this episode, we cover:

• Why AI agents require continuous improvement—not one-time setup
• The biggest misconception companies have about AI adoption
• How AI compares to training and managing human employees
• The role of iteration in building effective AI systems
• How AI + nearshore talent creates a competitive advantage

If you're exploring AI, automation, or nearshore hiring strategies, this episode provides practical insights you can apply today.

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

In this short clip from The Nearshore Cafe Podcast, Brian Samson discusses why Venezuela may become one of the most exciting high-risk, high-reward talent markets in Latin America.

He explains what the country looked like before the recent political shift, what Venezuelans are experiencing today, and why companies looking to hire globally should keep an eye on the country’s evolving talent landscape.

Watch the full episode:
https://youtu.be/TRlSVqnrzEs

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

In this episode of The Nearshore Cafe Podcast, Brian Samson speaks with Joe Helleny, Founder & CEO of CourtMoney, about building a 24-hour nearshore call center in Central America.

Joe shares how his background in ATMs, online payments, and government software led him to outsource customer support — first in the U.S., then nearshore in Nicaragua. He discusses the challenges of English proficiency, professionalism, background checks, handling financial transactions, and knowing when founders need to step out of day-to-day support.

Topics include:

• When to outsource customer support
• U.S. vs. international call centers
• Why Central America became the right solution
• Managing complex payment calls
• SaaS, AI, and automation in utility billing
• Expanding nearshore beyond call centers

If you're evaluating nearshore staffing or building a remote support team, this episode offers a practical founder perspective.

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

In this episode of The Nearshore Cafe Podcast, host Brian Samson sits down with entrepreneur and expat founder Chad Smalley to explore what it really takes to build and scale businesses in Panama and Colombia.

Chad shares how his journey began in Panama in 2007, where he built and scaled a Spanish-language CRM serving nearly the entire real estate market. From there, the conversation moves into Colombia — comparing Bogotá vs Medellín, discussing hiring, cultural loyalty, startup opportunities, and why Latin America can offer a strategic advantage for founders.

The episode also dives deep into the rapid rise of influencer marketing, UGC, and TikTok Shop, including why TikTok Shop generated $500 million in a single day on Black Friday and what that signals for the future of social commerce — especially in Latin America.

If you’re an entrepreneur, investor, operator, or exploring nearshoring and LATAM market expansion, this episode is packed with practical insight.

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast

In this episode of The Nearshore Cafe Podcast, host Brian Samson is joined by JP Trouillot, Deal Advisory Partner and Regional Advisory Leader for the Americas at KPMG, and Alan Riddell, Head of Deal Advisory for Brazil and South America at KPMG Brazil.

Together, they explore the evolving M&A landscape in Latin America and why investor confidence is rising heading into 2026. Drawing from KPMG’s global executive research and real-world deal experience, this conversation unpacks how sophisticated investors are approaching risk, valuation, and growth in a region long known for volatility.

This episode covers:

• The current and future M&A outlook in Latin America
• Why Brazil and Argentina are attracting renewed foreign investment
• How high interest rates are reshaping deal structures, earnouts, and valuations
• The shift from risk avoidance to risk architecture in cross-border M&A
• Nearshoring, supply chain realignment, and buy-versus-build strategies
• Infrastructure, energy, data centers, and technology as key growth sectors
• Post-merger integration, leadership, culture, and talent considerations

If you’re a founder, investor, executive, or operator looking to understand where capital is moving and how deals are actually getting done in Latin America, this episode delivers practical insight you can apply immediately.

🎧 Host | Brian Samson – Founder of 💻 Plugg Technologies
🔗 https://www.linkedin.com/in/briansamson/

🎙️ Sponsored by Plugg Technologies – Connecting U.S. companies with top-tier software developers across Latin America.
🌐 https://www.plugg.tech

🌎 Follow The Nearshore Cafe Podcast
🎵 Spotify: https://open.spotify.com/show/6KYcgpmN77fJm6B25469B8
🎙️ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-nearshore-cafe/id1775525954
💼 LinkedIn: https://www.linkedin.com/company/the-nearshore-cafe
🌐 Website: https://www.nearshorecafepodcast.com
🔗 All links: https://linktr.ee/nearshorecafepodcast