Episodes

  • Can You Tour 45 Weeks a Year and Still Call It Love? with Jackie Kashian

    Can You Tour 45 Weeks a Year and Still Call It Love? with Jackie Kashian
    Jun 24 2026
    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. Hear the bonus version at http://patreon.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 1 min
  • What If Your Endgame Isn't to Get Bigger? with Mike Draper

    What If Your Endgame Isn't to Get Bigger? with Mike Draper
    Jun 17 2026
    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." Plus, a bonus conversation at http://patreon.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 6 mins
  • What If 30 Years Is Just The Beginning? with Rhett Miller

    What If 30 Years Is Just The Beginning? with Rhett Miller
    Jun 10 2026
    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. Get more at http://patreon.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    57 mins
  • How Do You Cover the Biggest Story of Your Life With No Institution Behind You? with Gillian Brockell

    How Do You Cover the Biggest Story of Your Life With No Institution Behind You? with Gillian Brockell
    Jun 3 2026
    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. Hear the bonus conversation at http://patreon.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 10 mins
  • What Happens When the People Building the Technology Stop Being Fans? with Anil Dash

    What Happens When the People Building the Technology Stop Being Fans? with Anil Dash
    May 27 2026
    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. Support the show at http://patreon.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    59 mins
  • What If Your Runway Is Weeks, Not Months? with Olivia Messer

    What If Your Runway Is Weeks, Not Months? with Olivia Messer
    May 20 2026
    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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    51 mins
  • Can You Win Three Emmys and Still Wonder If the Check Will Clear? with W. Kamau Bell

    Can You Win Three Emmys and Still Wonder If the Check Will Clear? with W. Kamau Bell
    May 13 2026
    W. Kamau Bell, Emmy and Peabody Award-winning comedian and filmmaker, joins us to talk about what it actually looks like when the industry that rewarded you for doing the right thing quietly decides it's done doing that. We get into the real math of basic cable money, and what happens to a career built on diversity and inclusion when DEI becomes a liability. Three kids. Nine jobs. Every dollar, he has to go grab. Still making his own gravy. Get more at http://pateron.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 5 mins
  • What If Your Biggest Client Has Never Heard of Your Other Career? with Kim Newmoney

    What If Your Biggest Client Has Never Heard of Your Other Career? with Kim Newmoney
    May 6 2026
    Los Angeles-based photographer Kim Newmoney has shot for HBO, Showtime, Vogue, and Comedy Central. We get into what it actually takes to build a freelance photography career from the ground up, how a nail salon a 600,000 chickens play a role, and what all of it taught her about how to walk onto any set and make anyone comfortable in front of a lens. Hear the full episode at patreon.com/pastdue Learn more about your ad choices. Visit megaphone.fm/adchoices
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    47 mins