What happens when leverage, confidence, and speculation collide? Jake and Cory begin this episode by discussing a highly leveraged hedge fund and the risks of investing with borrowed money. They also explain how options strategies may help executives manage concentrated company stock before turning to a deeper question: Is retiring as early as possible really the right goal?

The conversation explores the difference between financial independence and leaving work, why purpose remains important in retirement, and why a complete retirement plan should address what you are retiring to—not only whether you can afford to stop working.
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