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Q&A: The Goalposts Moved — Is That Actually a Problem?

May 26, 2026

#718: What happens when the financial strategy that once felt obvious suddenly becomes a lot more complicated? Les is approaching financial independence but has realized there’s one thing missing from the traditional FIRE equation: how do you continue meaningful charitable giving after you stop earning a paycheck? Jaime has built a sizable retirement portfolio, but now he’s wondering whether the complexity inside his 401(k) actually matters—or if he’s overthinking the mechanics of retir...

The 5 Ways Investors Behave When Things Go Wrong, with Clare Flynn Levy

May 22, 2026

#717: Clare Flynn Levy was a hedge fund manager in London in the summer of 2007, watching her trading screens turn red — every single day. Merger arbitrage spreads were widening. Investors were pulling out. She didn't yet realize she was watching the early tremors of a global financial crisis. Clare joins us to talk about what that experience taught her about investor behavior, emotional bias, and the hidden forces that drive financial decisions. She now runs a firm that helps professional ...

Q&A: Your Kids Just Inherited $350,000 Each. Now What?

May 19, 2026

#716: When does a financial decision stop being purely about maximizing returns—and start becoming about building the life you actually want? Karen recently inherited sizable trusts for their children and is now navigating the complicated intersection of investing, taxes, legacy planning, and future financial aid eligibility. Matt has spent years building a solid index fund portfolio, but as retirement gets closer, he’s wrestling with a familiar investor problem: how do you know when...