Buy, Borrow, Die... How America's Tax Code Built a New Aristocracy

America doesn’t tax wealth. It taxes people who need paychecks. In this episode, we break down Ray Madoff’s The Second Estate and the playbook behind America’s new aristocracy: buy, borrow, die. Billionaires can borrow against appreciated stock, avoid selling assets, donate shares for tax benefits, use trusts to move wealth, and die with a stepped-up basis that can erase decades of capital gains. From Jeff Bezos and Elon Musk paying zero federal income tax in certain years, to Peter Thiel turning a $2,000 Roth IRA into a $5 billion tax-free account, this isn’t tax evasion. It’s the system working as designed. The deeper problem: untaxed dynastic wealth doesn’t just buy yachts. It buys media, think tanks, policy influence, and power.

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🔗 Resources:

How billionaires have such a significantly lower tax rate (Ezra Klein via New York Times Opinion)

The tax avoidance playbook (Ray Madoff via Vox)

The Second Estate — Ray Madoff (Book) (University of Chicago Press)

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