
The Stacking Benjamins Show Your Money Problems Aren't Math Problems (They're People Problems) SB1751
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Oct 22, 2025 In this discussion, Carl Richards, a financial planner and New York Times columnist known for his insightful 'Sketch Guy' drawings, shares invaluable insights on why money problems are often about emotions rather than equations. He emphasizes the importance of personal stories in financial decisions and suggests starting conversations with intimate questions. The hosts also delve into the complexities of options trading, debating their legitimacy as a risk management tool versus just financial gimmickry. Tune in for practical advice on simplifying your financial life!
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Money Is Mostly Stories
- Money often feels like an emotional story, not a neutral math problem.
- Carl Richards says our money fights come from layered stories, not arithmetic.
Start Close In With Questions
- Start financial conversations close to home with simple questions and empathy.
- Ask about first memories of money to reveal underlying money stories and values.
Eighth Grade Bike Lesson
- Joe saved $450 for a 12-speed bike in eighth grade but wrecked it and couldn’t afford repairs.
- That experience taught him to consider maintenance and long-term value before purchases.


