The Jay Martin Show How to Become an Expat and Multiply Your Wealth
Aug 30, 2025
Jesse Day, an insightful expat and commentator on political and cultural issues, shares his transformative journey of living abroad. He discusses the allure of escaping cultural misalignment and political discontent. The conversation dives into practical strategies for relocating, addressing benefits like lowered living costs and favorable taxes. Jesse also critiques the dynamics of individual freedom versus government control, and the complexities of navigating today's political landscape. His experiences in places like Croatia and Serbia offer a unique perspective on expat life.
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From Canada To Croatia And Serbia
- Jesse Day moved from Canada to Beijing in 2007, then lived eight years in Seoul and later left Canada during the pandemic for Croatia and Serbia.
- He sought countries with fewer restrictions and cultural alignment, ultimately settling where faith and mistrust of government matched his values.
Cultural Misalignment As A Migration Driver
- Cultural misalignment and political 'homelessness' drove Jesse to plan an exit rather than endure social estrangement.
- He emphasizes long-term planning and achieving remote-work autonomy before relocating permanently.
Plan A Multi-Year Exit
- Plan a multi-year exit strategy if you can't move immediately; aim for two to five years of preparation.
- Prioritize remote-work or online business models so you aren’t tied to a local job before relocating.
