Armchair Expat

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 cultur