Dear Media Turned Webster Hall Into The Internet’s Best GNO Ever

No one understands the women’s podcast universe quite like Dear Media. And now, the brand is taking its live listening experiences outside of the studio and into the club with Dear Media By Night.

What started as a podcast passion project in 2016 has transformed into the largest female-focused podcast network to date. Founded by Michael Bosstick in 2018 alongside his wife, Lauryn, who’s also his co-host and founder of The Skinny Confidential – a blog turned product line. The two have driven their show, The Bossticks, to #1 in education on Apple podcasts, and highlight up-and-coming voices in the space.

Their next move is meeting listeners where they are. “We're starting to explore other formats that live and go beyond the traditional podcast,” Bosstick tells Bustle. That’s where Dear Media By Night comes in.

On Saturday, May 16, members of the network’s cult following hung up their headphones to meet IRL at Webster Hall in New York for the event. “We launched By Night as a ‘girls' night out’ iteration that’s part cocktail hour, part pop culture, and a little bit of comedy,” Bosstick says. “A Dear Media By Day is next, which will be more health, wellness, and career-focused.”

Upon entering Webster Hall’s dark foyer, a neon-lit bar and hot pink photo booth paved the way for guests to take their seats for the show, where Taylor Strecker, host of the podcast Taste of Taylor, introduced live episodes with fan-favorite Dear Media creators. The lineup included some of the network’s top entertainers like Josh Peck and Ben Soffer of Good Guys, Claudia Oshry and Jackie Oshry from The Toast, and Not Skinny But Not Fat’s Amanda Hirsch.

“There’s nothing like hearing the audience react in real time,” Hirsch says of the event. “And obviously having Amy Schumer come out [as a surprise guest] took it to another level and made the whole night feel pretty iconic.”

As the night came to a close, the audience burst into an on-brand singalong of 2000s hits with the Oshry sisters (IYKYK). As expected, the crowd was just as much part of the show as the performers themselves, and that sort of intimate participation was the whole point. As Bosstick says, being present was the entire vibe of the night: “At an event like this, you can't just be stuck in your own element. You have to pay attention to what's going on around you.”