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Bonus: The House That Loopholes Built

Aug 8, 2026 · 12m

Summary

The hosts discuss AQR Capital’s sophisticated tax-loss harvesting strategy, which generates "tax alpha" by engineering losses to offset gains. This sparks a debate on whether the ultra-wealthy, like Cliff Asness, should continue working or simply pay taxes and retire. They humorously propose a $100 million threshold for mandatory retirement, excluding artists, and question if billionaire labor benefits the economy.

Topics discussed

Introduction to AQR Capital and tax-loss harvesting How traditional tax-loss harvesting works AQR's leveraged long-short strategy for tax alpha Critique of the 'working rich' and tax avoidance Debate: Would the economy suffer if the rich stopped working? Retirees, leisure spending, and the definition of work Setting a wealth threshold for mandatory retirement Inheritance, volunteer work, and Elon Musk's happiness
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