How To Actually Tax The Rich — ft. Ray Madoff
May 22, 2026
Summary
Prof G and Ed discuss their upcoming live tour before interviewing tax expert Ray Madoff about wealth inequality. Madoff explains how the ultra-wealthy avoid taxes by borrowing against appreciating assets rather than taking salaries. He argues for taxing unrealized gains upon transfer, repealing the ineffective estate tax to include inheritances in income tax, and equalizing capital gains rates with ordinary income.
Topics discussed
Sponsors: Amazon, Hostinger, and Meta Ray-Ban
Tour dates, J.P. Morgan anecdotes, and Billions cameo
Introduction of Ray Madoff and the tax inequality myth
How the wealthy avoid taxes via loans and asset appreciation
Proposed solutions: Taxing appreciation and repealing estate tax
Sponsors: Verizon, Monarch Money, and SoFi
The history and failure of the estate tax and loopholes
Inheritance tax, political influence, and capital vs. labor rates
Equalizing tax rates and the 1986 Tax Act history
Why wealth taxes fail and the need for comprehensive reform
Deficit issues, AI's impact on tax revenue, and conclusion
Credits and final sponsors: iSIMS and Blinds.com
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