Episode
312: Why Paying More in Taxes Can Make You Wealthier
- Published
- Sep 15, 2026
- Duration seconds
- 408
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Summary
You could pay more in taxes and still end up with more money. That sounds wrong at first, because most people assume the goal is always to pay as little tax as possible. But for high earners with appreciated assets, that instinct can actually cost millions over time. Hilary Hendershott explains why the timing of taxes can matter just as much as the amount of taxes paid. Imagine you have $4 million in company stock. If you sell it all at once to diversify, you may trigger a large tax bill imme...