In November 1995, Ira Glass quietly launched the first episode of This American Life. The rest, as they say, is history. Today his show is a colossal success and Ira Glass is a household name. But in the intervening two decades, Ira has left an indelible mark on the industry by helping to shape hundreds of podcasts as well as hundreds of podcasters — including Alex. On this episode, Alex sits down with his mentor and former boss to talk about the early days at This American Life, what Ira taught Alex, and how being a good boss means learning to set people free.

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Nina Jacobson is a force in Hollywood. She’s behind some of the biggest movies of the last 20 years: The Sixth Sense, Pirates of the Caribbean, The Chronicles of Narnia, The Hunger Games, and most recently Crazy Rich Asians. She’s had a lot of success. But also some pretty big failures: a public firing, some box office flops. Nina walks Alex through her failure resume and talks about what it takes to make a hit.

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Dapper Dan made a name for himself as one of Harlem’s premier fashion designers in the 1980s, creating unique leather designs covered in counterfeit logos from brands like Gucci and Louis Vuitton. But when the fashion houses found out, they shut him down. So how, 20 years later, did Dapper Dan make it to the top of the world that put him out of business? 

We created a playlist of some of the songs that name-drop Dapper Dan, from artists like LL Cool J, Missy Elliott, and Pusha T... You can find it exclusively on Spotify, at open.spotify.com/playlist/6Gl7MBd1RvVT4ihFVrSaqF?si=H6XBdhYHTTW8aBzbUhLXaQ.

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As acquisition talks with Spotify continue, Alex and Matt face their hopes and fears about what might lie ahead.

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Just days before Thanksgiving, Alex and Matt board a red-eye to Stockholm for a conversation that could change everything.

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It's the spring of 2018, four years after Alex and Matt launched Gimlet, and things are not going well. Audiences are flat, ad sales are flagging, and the company is burning through cash at an alarming rate. And with all of those pressures, Alex and Matt have started to fight.

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Five years ago, StartUp began chronicling the life of a fledgling Brooklyn-based podcasting company called Gimlet Media. This year, the streaming giant Spotify bought that company. In the final season of StartUp, what it's really like to sell a business.

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Alex introduces an episode of The Journal. about companies monitoring their workers. It's common, it's legal. And it can lead to employers having surprisingly personal information about the people who work for them.

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Jenny Doan and her husband, Ron, lost most of their savings in the 2008 financial crisis. Retirement was just around the corner, and they didn’t know how they would make it through. That’s when the family went all-in on an unlikely business—a quilt shop.

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As a Democrat from a red state, Senator Heidi Heitkamp built a reputation for her willingness to buck party pressure and reach across the aisle. But when Brett Kavanaugh was nominated to the Supreme Court, she found herself facing a decision between her principles and her political fate.

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