What if debt isn't a personal failure—but a symptom of a much bigger problem?
For years, we've been told that financial struggles come down to individual choices: spend less, budget better, work harder. But what if the real story is more complicated?
My guests today are Jamie Feldman and Rachel Webster, creators and hosts of the award-winning podcast Debt Heads, a groundbreaking series they describe as a \"true crime investigation into the murder of our bank accounts.\" The podcast is now entering season 2.
Season one began with Jamie's own experience navigating credit card debt and the shame that came with it. But what started as one woman's debt payoff journey quickly evolved into a deeper investigation into the systems, cultural pressures, and economic realities that leave so many people feeling financially stuck.
Jamie is a writer, editor, and storyteller. Rachel is a filmmaker and producer. Together, they've built a fiercely honest, deeply funny, and surprisingly hopeful podcast community around a topic most of us avoid talking about: money.
Now, as Debt Heads returns for its second season, they're widening the lens beyond spending and debt to explore work, job security, income instability, and what it means to pursue financial wellbeing in a world that often feels increasingly precarious.
In our conversation, we talk about the hidden connections between mental health and money, why so many women tie their self-worth to spending, how shame keeps us isolated, and why financial security is about far more than your net worth.
You'll also hear their thoughts on the creator economy, the pressure to monetize every passion project, and why making meaningful work—not just profitable work—can lead to unexpected opportunities.
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