Comedian Adam Conover joins us to unpack the real costs of the so-called "creator economy" from algorithmic gatekeeping to the crumbling of stable creative jobs.

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Alex Goldman, co-creator of Reply All and current host of Hyperfixed joins us to talk about what it actually looks like to start over. We get into 18 months of floundering and how he ended up funding Hyperfixed with a $200,000 loan he's still paying back.

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Actor, comedian, and podcaster Connor Ratliff joins us to talk about building a creative life out of the parts you can actually control. We get into SAG insurance that resets every year and what it actually means to lose a Spielberg role and feel genuinely okay about it.

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Stand-up comedian Jackie Kashian joins us to talk about 40 years on the road and what it actually takes to stay in love with a job that never stops moving. We get into the real math of touring across four decades, why a 20-year-old podcast might be her smartest business decision yet, and what it costs to keep choosing the road over almost everything else.

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Mike Draper, founder of Raygun, the greatest store in the universe, joins us to talk about what it costs to stay in control of something for 21 years. We get into the real math of brick-and-mortar retail, the night he was $800,000 underwater with a hospitalized wife and a newborn at home, and what it actually means to build a business around "enough."

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Musician and writer Rhett Miller joins us to talk about staying creative in an industry that keeps changing. From fronting the Old 97’s to writing children’s books, Rhett opens up about the financial rollercoaster of life on the road, the loneliness of independence, and the challenge of keeping faith in your work when the world stops clapping.

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Journalist Gillian Brockell spent a decade at the Washington Post, took a buyout thinking she'd be back in two years, and watched the place fall apart from the outside. She joins us to talk about what it actually cost to leave, why the buyout money wasn't Bezos being generous, what happened when she filed a major Emmett Till story and the new editors tried to make the bad guy look less bad, and how she ended up becoming what may be the only journalist in America covering ICE deportation flights full time.

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Technologist, writer, and self-described "big fan of being a big fan" Anil Dash joins us to talk about what it looks like to spend 25 years watching tech eat everything from journalism to musict to blogging, and now the jobs of the people who built it. We get into 750,000 tech layoffs and counting, why the "learn to code" safety net is gone, and what happens to the creative economy when the partner who was supposed to be funding the dream loses their job too.

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Olivia Messer, journalist, novelist, and editor-in-chief of The Barbed Wire, joins us to talk about what it actually looks like to run an independent Texas newsroom. We get into why virality and revenue have essentially no relationship to each other, what she learned sitting on the management side of a union negotiation for the first time, and what happens to your own creativity when every single day is a budget meeting.

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