Jenna Weiss-Berman, co-founder, Pineapple Street Media

The podcast pioneer has come up with ideas so crazy, they actually work

Says Weiss-Berman: "I think a lot of people have amazing stories and don’t fully know how to tell them" (Photo by Jon Premosch, courtesy of Pineapple Street Media)

Jenna Weiss-Berman is a co-founder and producer at Pineapple Street Media, the Brooklyn-based podcast company responsible for some of the most novel shows of our time, including Missing Richard Simmons, Still Processing and Women of the Hour with Lena Dunham. 

Weiss-Berman has more than a decade of media experience, with stints at NPR, The Moth and StoryCorps, a sweeping oral history project. At StoryCorps, she traveled around the country and helped people craft their own history. “I really like helping other people tell stories,” she told us in our podcast. “I think a lot of people have amazing stories and don’t fully know how to tell them.” 

Weiss-Berman went on to create Buzzfeed’s podcast department in 2014, as the podcast boom was taking off. “They had never done podcasting before. That meant that I was not just making shows but figuring out legal contracts and hiring people and finding sponsors.” Her pioneering work led to successful shows such as Another Round, whose hosts Tracy Clayton and Heben Nigatu have since been described by The Guardian as “leading American cultural critics.” 

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While wrapping up her time at Buzzfeed, Weiss-Berman was approached with the idea of starting a podcast company. “I never set out to be an entrepreneur; it was never something I wanted to do, but I was like ‘I have these skills, I think I could do this.’” She and her co-founder Max Linsky had already lined up potential partnerships with Dunham, Hillary Clinton, the New York Times and ad agency Wieden+Kennedy. “Everything we have some kind of a partner on. We have done things with Google, Clinique and Morgan Stanley. Most of what we do is creating original content, but with partners.”

One of the company’s most notable collaborators was Clinton, who sat down with Pineapple Street for a series of candid conversations about America and the campaign trail. The podcast, called With Her, also included interviews with Bill Clinton and Sen. Tim Kaine. Other originals produced by the company include Heaven’s Gate, about a religious cult, and Never Before with Janet Mock, a series of interviews with leading cultural figures.

Unlike many startups, the Pineapple team decided not to raise money from venture capitalists, which Weiss-Berman believes has liberated Pineapple to go deeper with unique and edgy content. “When we started Pineapple, we wanted people to say ‘no’ to us. We wanted to ask for things that were so crazy, and come up with story ideas that were so crazy, that people would be like, ‘No, that’s crazy.’ And it hasn’t happened yet. We keep asking people to do crazy shit with us and they keep saying ‘yes.'”–By Kora Feder