Wrestler and podcaster Colt Cabana joins Ana and Mike to talk about building a life in wrestling. From getting fired by WWE to becoming a blueprint for sustainable DIY success, Colt breaks down the real economics of creative work—merch tables, mattress money, and all—and why betting on yourself might be the best decision you ever make.

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Comedian and writer Joey Clift returns to talk about first book deal money, the evaporation of publisher marketing, self-financing a 22-date tour, and why tribal casinos are actually closer to socialism than capitalism.

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Stand-up comedian and former NPR host Ophira Eisenberg joins us to talk about what happens after the salary ends. We get into public radio money, Sirius XM royalties, and the Gen X guilt of making content.

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Malcolm Barrett joins us to break down exactly how streaming, with it's shorter seasons, invisible metrics, and evaporating residuals, might be breaking the working actor. 

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Comedian, writer, and union organizer Nato Green joins us to talk about 30 years of building worker power by day and doing stand-up by night, and why he's made peace with the fact that comedy will never be his primary income. Plus, how to negotiate any creative contract without getting screwed.

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Actor, writer, and registered ER nurse Ambar Martinez joins us to talk about building a life out of two careers that are both all-consuming... and refusing to pick just one. We get into the economics of nursing your way through an acting career, how medical advising became its own income stream, and what it costs to keep proving yourself in two industries that each assume the other one is your real job.

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Journalist and podcast host Sam Sanders joins us to talk about what happens when the thing you thought you wanted turns out to be too small. We get into the emotional and financial cost of walking away, what it means to do it yourself in a collapsing industry, and how to balance ambition with reality.

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Jamie Feldman and Rachel Webster, the duo behind the award-winning podcast Debt Heads, join us to talk about the 1978 Supreme Court decision that quietly eliminated interest rate caps and created the modern credit card crisis, why shame is the most profitable tool the financial industry has, and why the answer to "how did we all end up here" is never as personal as we've been told.

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Mike's running at full speed with no room to breathe, Ana's navigating the gap between making art and making rent, and together they unpack why showing up, week after week, broke or not, might be the only honest answer left.

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Writer and author Rainesford Stauffer joins us to talk about what happens when you've spent your whole life working your way into worthiness and it still doesn't feel like enough. We get into the real economics of freelancing plus nonprofit work plus mentoring student journalists in Kentucky, what OCD has to do with financial anxiety, and what she actually tells young people entering the worst job market of their lifetimes. 

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