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Why Everyone Is Drowning In Debt (and how to get out) - Caleb Hammer - #1123

Explore episode Jul 13, 2026
Business
Is Property Still a Smart Investment? Caleb Is Selling Out

Why Everyone Is Drowning In Debt (and how to get out) - Cal… · Jul 13, 2026 Business

Real estate has consistently underperformed the S&P 500 in recent history. Caleb is exiting all his rental properties for index funds — no tenant headaches, no unpredictable repair bills, and better returns. The only edge property has is leverage, and that's a double-edged sword most landlords don't respect.

Where this was said

How Money Problems End Relationships

At 1:34:59 · chapter starts 1:34:24

Chris and Caleb explore how mental health shapes spending behaviour, and the answer is darker than most personal finance content acknowledges. When you're depressed or stressed, a purchase delivers a dopamine spike that momentarily alleviates the pain — and when you're poor, you have fewer sources of that dopamine, making frivolous spending a more attractive coping mechanism. Cigarettes are the canonical example: they alleviate suffering in the moment even as they deepen financial and physical harm. Chris reaches for Sam Harris's white privilege framing — the psychological luxury of never assuming a bad outcome is racially motivated — as an analogy for the invisible psychological loops that being poor creates. Being poor shapes how you interpret your situation, how you cope with it, and how you behave in ways that make escaping poverty harder. Social media compounds everything: it raises the baseline dopamine threshold so that ever-larger stimuli are needed to feel anything, while simultaneously showing people aspirational lifestyles that intensify the comparative pain of being where they are. Both hosts agree: poor people will go broke trying to look rich, and the car is the most common vehicle for that impulse.

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