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Welcome to The Nearshore Cafe Podcast, hosted by Brian Samson and sponsored by 💻 Plugg Technologies (plugg.tech), a nearshore talent partner connecting U.S. companies with English-speaking software engineers and digital talent across Latin America. In this episode, Brian sits down with longtime entrepreneur Joe Helleny, Founder & CEO of CourtMoney, to discuss how U.S. companies can successfully build a 24/7 nearshore call center in Central America. Joe shares his journey from fourth-generation entrepreneurship in Southern Illinois to building ATMs, launching online government payment systems, and expanding into full-scale municipal software development. The conversation explores how and when founders know it’s time to outsource support — and how nearshoring became a strategic advantage. Together, they break down: • When founders should step out of day-to-day support • Building a 24-hour call center operation • Lessons from U.S.-based call center partnerships • Transitioning to Central America nearshore teams • English proficiency and professionalism concerns • Handling sensitive financial transactions offshore • Time zone vs. quality tradeoffs • AI, automation, and the future of SaaS in payments Joe explains how his Nicaragua-based team became more than just a cost solution they became a long-term operational partner. 🎧 If you’re a founder, SaaS operator, or business owner exploring nearshoring, customer support outsourcing, or Central America call center solutions, this episode delivers real-world insight. Sponsored by Plugg Technologies 👉 https://www.plugg.tech Learn more about CourtMoney 👉 https://www.courtmoney.com ⸻ ⏱️ Chapters 00:00 – Welcome & Sponsor (Plugg Technologies) 01:01 – Meet Joe Helleny (CourtMoney) 03:31 – Building a Portfolio of Businesses 04:06 – Staffing Challenges in Rural America 09:56 – When to Launch a Call Center 12:49 – Designing a Call Center System 14:25 – U.S. vs Philippines Outsourcing 16:21 – First Thoughts on Latin America 19:09 – Vetting a Nearshore Team 20:30 – English & Professionalism Concerns 22:22 – Handling Complex Customer Scenarios 24:31 – AI, SaaS & The Future of Payments 26:52 – Expanding Beyond Call Centers ⸻ 🎙️ Host Brian Samson Host, The Nearshore Cafe Podcast Sponsor: 💻 Plugg Technologies Website: https://www.plugg.tech ⸻ 🎙️ Guest Joe Helleny Founder & CEO, CourtMoney 🌐 Website: https://www.courtmoney.com 📧 Email: joe@courtmoney.com ⸻ 🎙️ Sponsored by Plugg Technologies Connecting U.S. companies with vetted software engineers and digital talent across Latin America. Website: https://www.plugg.tech ⸻ 🌎 Follow The Nearshore Cafe Podcast Website: https://www.nearshorecafepodcast.com Linktree: https://linktr.ee/nearshorecafepodcast