Journalist and 404 Media co-founder Jason Koebler joins us to talk about what it takes to build an independent newsroom. From the cost of defamation insurance to the weight of mailing your own merch, we get into the invisible math of staying scrappy without burning out—and the true cost of reader-supported journalism.

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Broadcaster and podcast pioneer Jesse Thorn joins us to talk about building something sustainable without selling out. From his early days of mailing CD-Rs to NPR stations to running Maximum Fun as a listener-supported network, Jesse shares the emotional and economic math behind 20 years of independent success. We get into what it means to build trust with an audience, how community gets harder in a platform-driven world, and why “working for the people” still feels like the best job he’s ever had.

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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 podcaster Babs Gray joins us to talk about staying creative in the long middle—the part where the dream hasn’t died, but it hasn’t fully arrived either. We get into the quiet power of community, the joy of weird little projects, and why success isn’t always loud. From survival jobs to self-trust, Babs reminds us that showing up for your work, even when no one’s watching, might be one of the most important things you can do.

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Comedian and actor Will Hines joins Ana and Mike to talk about trading a salary for freedom, and why time might be the only currency that really matters. From leaving a corporate job at 33 to building an improv school from the ground up, we get into the real economics of creative work: how to manage taxes, protect your energy, and figure out what’s worth outsourcing (and what’s not).

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Actor and comedian Jacquis Neal joins us to talk about the strange space between doing good work and still feeling like you haven’t arrived. From voiceover gigs to the long-haul hustle, we explore what it means to trust the process when the results don’t always look like what you imagined.

Want more? On the bonus episode, Jacquis opens up about the thing he keeps doing—whether or not anyone’s watching. Subscribe at patreon.com/pastdue for that, plus early access, ad-free episodes, and more.

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Comedian River Butcher joins us for a conversation about what happens when the gigs stop coming—and the world doesn’t end. We talk about the fear of slowing down, and how gratitude, perspective, and a working fridge might just be the real signs of success.

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Writer and video essayist Michael Burns joins us to talk about what happens when the platform you helped build stops serving the work and starts serving itself. After Wisecrack, he set out to make something smaller, stranger, and more his own. We get into the emotional cost of reinvention, the illusion of creative security, and why doing it yourself might be harder… but also the only honest way left.

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Ana and Mike compare notes from the road: Ana’s on assignment in small-town Maine chasing a political story she believes in, and Mike’s in between tour legs, chasing rent. They get into the economics of chasing meaning when the math doesn’t make sense, the disappearing budgets of real journalism, and why a DIY ethos is both a burden and a blessing.

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