Launching a media property is never easy, but from the outside, at least, the story of Pineapple Street’s early days certainly seem charmed. The network counted among its earliest hosts then-presidential candidate Hillary Clinton. There aren’t too many people in the world who bring more star power to the table. The network has launched numerous high profile shows since With Her, including Lena Dunham’s Women of the Hour podcast and the surprise runaway hit, Missing Richard Simmons. Jenna Weiss-Berman cofounded the company in 2016, leaving a cushy gig at Buzzfeed to enter the uncertain world of startups. “I always wanted to work in either homeless services or make podcast,” she explains during our chat at the OnAir Fest in Brooklyn. “I want to do things that feel like they’re making a difference.”

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