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Toby Mathis
How Do Offshore Corporations and Trusts Work in the US

Join Toby Mathis, Esq., as he speaks with international tax expert Jimmy Sexton, LLM., the Founder & CEO of Esquire Group, about unraveling the enigma of offshore banking and its impact on US taxpayers. Despite popular belief, Jimmy reveals that the era of offshore banking providing substantial tax benefits is over, with the true perks lying elsewhere such as asset protection and market access. We navigate through the murky waters of tax evasion myths and scrutinize how various income structures, including disregarded and taxable entities, bear on one’s tax obligations. Moreover, Jimmy illuminates the effects of the GILTI and Subpart F tax regimes on foreign company profits, stressing the importance of understanding the intricate US tax code to avoid hefty penalties and ensure compliance.


  • Offshore banking myths vs. reality for US taxpayers
  • Tax advantages from asset protection, not tax savings
  • Misconceptions about offshore tax evasion
  • Implications of GILTI and Subpart F tax regimes
  • Complexities of international business operations
  • Benefits of Foreign-Derived Intangible Income (FDII)
  • Major corporations adapting to tax law changes- Google and Amazon
  • Tax reforms encourage repatriation and competitiveness
  • Severe penalties for non-compliance with FBAR regulations
  • Compliance demands of offshore structures versus domestic
  • Corporate Transparency Act and international standards


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Full Episode Transcript:

Toby: Hey, guys. Toby Mathis here, and I have Jimmy Sexton, a longtime friend, colleague. He’s in the world of international tax. We’re going to demystify offshore banking, doing business offshore, and when that stuff makes sense. First off, welcome, Jimmy.

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