What separates smart financial planning from a federal crime? In this episode, we break down the critical distinction between tax avoidance—the legal use of the tax regime to reduce liability—and tax evasion, the illegal misrepresentation of financial affairs to defeat the imposition of taxes.

We explore the complex world of tax shelters, examining legitimate vehicles like 401(k) retirement plans alongside controversial "abusive" schemes involving offshore companies and artificial losses. We also unpack the aggressive strategies used by multinational corporations, such as the "Double Irish" and "Dutch Sandwich," to shift profits into tax havens.

Finally, we analyze the "tax gap"—the difference between taxes owed and taxes collected—and why the top 0.01% of the wealth distribution are statistically more likely to engage in evasion. Join us as we discuss how governments use judicial doctrines like "substance over form" to determine when a legal loophole becomes an illegal lie.