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Upticks: A Financial Planning & Investment Podcast

Upticks: A Financial Planning & Investment Podcast

Reasons People Can Go Broke Trying to Look Rich

Jul 2, 2026 · 35m

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On this episode

About this episode

What does financial freedom really look like? Are we chasing wealth or just the appearance of it? In this episode, Jake and Cory dive into the psychology behind money decisions, from homeownership and lifestyle inflation to raising financially independent children and resisting the urge to keep up with the Joneses. The conversation also tackles a question many parents wrestle with: when does helping your children become enabling them? Jake and Cory share perspectives on teaching financial responsibility, setting healthy boundaries, and preparing the next generation for independence. Plus, they examine why some multimillionaires still feel broke, how consumer culture influences spending…