What happens when you trade Miami traffic for Madrid tapas—and still have to keep the IRS happy? In this episode of Armchair Expat, Shannon Acton interviews Nicolas Castillo, founder of Rook International CPAs and Advisors, about the realities of building a life and business abroad. Nicolas shares his personal journey from Miami to Madrid, opening up about the challenges of adjusting to a new culture, the importance of community, and the very real complexities of cross-border tax planning. As a global tax advisor, Nicolas sheds light on what Americans often get wrong about filing from overseas, the myths around expat taxes, and why countries like France and Italy can be surprisingly friendly to entrepreneurs and retirees. Whether you’re considering a move abroad, already living overseas, or just curious about how cross-border life works, this conversation blends personal experience with practical, must-know advice. Nicolas moved to Spain three and a half years ago with his wife, choosing Madrid for its culture, language, and community feel. He contrasts the walkable lifestyle of Spain with the car-centered culture of Miami, and shares how building community abroad takes courage but pays off. From a professional perspective, Nicolas emphasizes that many Americans mistakenly believe they don’t need to file taxes once they leave the U.S.—a misconception that can lead to severe penalties. He explains citizenship-based taxation, highlights tax-friendly options in France and Italy, and stresses the importance of consulting a cross-border advisor before relocating. CONNECT WITH NICOLAS LinkedIn Website   DISCLAIMERThe information shared in this episode is intended for general educational and informational purposes only. It does not constitute legal, financial, or tax advice, and should not be relied upon as such. Everyone’s circumstances are unique—listeners are encouraged to seek professional guidance from a qualified advisor before making decisions about taxes, finances, or relocation.   ABOUT ARMCHAIR EXPAT Armchair Expat is hosted by Shannon Acton, founder and Chief Bargain Hunter of Bargain Homes Abroad Follow on Instagram  @bargainhomesabroad Visit our Website: https://www.bargainhomesabroad.co Subscribe to our E-Mail Digest: https://www.bargainhomesabroad.co/subscribe VIP Access: https://www.bargainhomesabroad.co/membership If you enjoyed this episode, please like, subscribe, and leave a review. It helps us reach more future expats and keep these stories coming.   ENTER THE REVIEW CONTEST: https://www.bargainhomesabroad.co/reviews   If you're interested in sponsoring or partnering with Armchair Expat, please reach out to Shannon at the following email: info AT bargain-homes DOT com