Uploaded September 2026 | Updated September 2026, 3 weeks ago
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.
Watch the fact check: youtu.be/T5-r8FSRLDQ
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 foundayo.lilly.com/risk
Start your 2 month free trial today: youtube.com/premium . Terms Apply. Cancel Anytime.
Check Allstate first for a quote that could save you hundreds: allstate.com
Watch Armchair Expert episodes: youtube.com/playlist?list=PLzPEuwClyOzDdlrAmU-IwKncG87qrF7Vw
Follow Armchair Expert on social:
instagram.com/armchairexppod
facebook.com/ArmchairExpPod
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About the Show:
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Watch Armchair Expert every MONDAY, WEDNESDAY, and FRIDAY here on Youtube!
Listen to episodes ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/shows/armchair-expert-with-dax-shepard
Chapters:
0:00 - Ray with an AY
5:26 - Tax Lawyer
12:45 - American Aristocracy
18:23 - We Have to Do Something About Taxes
32:02 - Changing Systems
43:37 - Estate Tax
52:39 - Choosing When To Pay Taxes
1:04:06 - Taxable Income
1:13:35 - Step Up and Bias
1:27:28 - How to Tax the Rich
#DaxShepard #ArmchairExpert #RayMadoff #TheSecondEstate #TaxCode #WealthInequality #AmericanAristocracy #TaxTheRich #BostonCollegeLaw #RayMadoffInterview #TaxPolicy #WealthGap #EstateTax #TaxLoopholes #DaxShepardInterview #ArmchairExpertPodcast #EconomicsInterview #TaxCodeExplained #BillionaireTax
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.
Watch the fact check: youtu.be/T5-r8FSRLDQ
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 foundayo.lilly.com/risk
Start your 2 month free trial today: youtube.com/premium . Terms Apply. Cancel Anytime.
Check Allstate first for a quote that could save you hundreds: allstate.com
Watch Armchair Expert episodes: youtube.com/playlist?list=PLzPEuwClyOzDdlrAmU-IwKncG87qrF7Vw
Follow Armchair Expert on social:
instagram.com/armchairexppod
facebook.com/ArmchairExpPod
twitter.com/armchairexppod
Connect with Wondery
wondery.com/shows/armchair-expert-with-dax-shepard
facebook.com/WonderyMedia
twitter.com/WonderyMedia
instagram.com/WonderyMedia
tiktok.com/@wonderymedia
About the Show:
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Watch Armchair Expert every MONDAY, WEDNESDAY, and FRIDAY here on Youtube!
Listen to episodes ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/shows/armchair-expert-with-dax-shepard
Chapters:
0:00 - Ray with an AY
5:26 - Tax Lawyer
12:45 - American Aristocracy
18:23 - We Have to Do Something About Taxes
32:02 - Changing Systems
43:37 - Estate Tax
52:39 - Choosing When To Pay Taxes
1:04:06 - Taxable Income
1:13:35 - Step Up and Bias
1:27:28 - How to Tax the Rich
#DaxShepard #ArmchairExpert #RayMadoff #TheSecondEstate #TaxCode #WealthInequality #AmericanAristocracy #TaxTheRich #BostonCollegeLaw #RayMadoffInterview #TaxPolicy #WealthGap #EstateTax #TaxLoopholes #DaxShepardInterview #ArmchairExpertPodcast #EconomicsInterview #TaxCodeExplained #BillionaireTax
