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.💥 Have you left your "honest ⭐️⭐️⭐️⭐️⭐️" review?This episode is proudly brought to you by Fridays. Because real wealth starts with your health. If you want to feel sharper, stronger, and more in control, visit joinfridays.com and use code HIGHER for an exclusive discount.📩 NEWSLETTER: https://tr.ee/O6FWkv👕 THS MERCH: http://www.thspod.com🔗 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)⚠️ Disclaimer: Please note that the content shared on this show is solely for entertainment purposes and should not be considered legal or investment advice or attributed to any company. The views and opinions expressed are personal and not reflective of any entity. We do not guarantee the accuracy or completeness of the information provided, and listeners are urged to seek professional advice before making any legal or financial decisions. By listening to The Higher Standard podcast you agree to these terms, and the show, its hosts and employees are not liable for any consequences arising from your use of the content.