EP410 How Canadians Can Legally Exit Canada’s Tax System with Bobby Casey

Glen Sutherland interviews Bobby Casey, an American international tax lawyer and “slowmad” who splits his time between North Carolina, Mexico, and Latvia. Bobby explains how his residency lifestyle works in practice, and why Americans are “unicorns” globally: the U.S. taxes citizens on a citizenship basis, meaning Americans still file (and may owe) U.S. taxes even when living abroad—though tools like the Foreign Earned Income Exclusion and foreign tax credits can reduce the hit. The conversation then shifts to Canadians and cross-border tax/residency strategy. Bobby outlines how Canadians can more easily exit Canadian tax residency by minimizing key residential ties (e.g., primary home, spouse, dependent children) and properly filing their departure return—while noting there can be exit-tax considerations and changed tax treatment of property kept behind. He also shares practical notes on living abroad (including why he disliked Belize) and digs into real estate rules for foreigners (e.g., Mexico’s restricted zones and use of a fideicomiso). Finally, Bobby explains why a U.S. LLC can be a powerful structure for non-U.S. digital nomads/remote entrepreneurs (depending on “effectively connected income” and where work is performed), and closes by describing his company formation/compliance platform, BusinessAnywhere.io.