Ray Madoff (on how billionaires avoid taxes & threaten capitalism)

Ray Madoff (on how billionaires avoid taxes & threaten capitalism)

From Armchair Expert with Dax Shepard by Armchair Umbrella

September 2, 2026 · 2h 26m · Episode 1096

About this episode

Ray Madoff discusses tax policy, wealth inequality, and the implications of billionaires on capitalism.

Ray Madoff (The Second Estate, Immortality and the Law, Practical Guide to Estate Planning) is a Boston College law professor, author, and tax-policy expert. Ray joins Armchair Expert to discuss being a proudly mediocre high school student, reluctantly trading philosophy for law school, and becoming a terrible Wall Street tax lawyer who loved teaching. Ray and Dax talk about America’s return to a pre-revolutionary aristocracy, how “salaries are for suckers” among the ultrawealthy, and why $50 trillion in wealth yielded only $28 billion in estate tax. Ray explains why high earners and wealth holders aren’t the same, how fair taxation could rescue capitalism, and why the problem is the system and not billionaires themselves. Thank you to our presenting partner Lilly. Lilly’s Foundayo™(orforglipron). Advertisement Disclaimer: Please see Indications and Safety Summary with Warnings for Foundayo™(orforglipron) at https://www.foundayo.lilly.com/risk  Start your 2 month free trial today: https://youtube.com/premium . Terms Apply. Cancel Anytime. Check Allstate first for a quote that could save you hundreds: https://www.allstate.com/  See Privacy Policy at…

People in this episode

Host: Dax Shepard

Guest: Ray Madoff

Topics covered

Keywords

Sponsors

Lilly, Allstate

Mentioned in this episode

Organizations: Boston College

Products: Foundayo™(orforglipron)

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