The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. In Episode 9, Gabe and Stella start with a deceptively simple question: when's the last time you changed your mind about something? Gabe's apartment flooded and he's temporarily on the Upper East Side — and within a week he realized he actually missed the dirty streets and broken glass of Soho. Stella spent her teenage years counting down the days until she could escape small-town Virginia, and now she wants a farm. Then they get into imposter syndrome — what it feels like to pull up to a historic LA studio with three iPhones and a GoPro, wondering if anyone's going to take you seriously, and why the lo-fi setup might actually be the whole point. And they close by pulling up their camera rolls from exactly a year ago — Gabe at Stagecoach, Stella on a solo walk through Brooklyn with no furniture and a full album — and realizing how unrecognizable they are from the people in those photos. New episodes every Monday. Part of the Almost Reckless universe from CP Media.
The Grey Area
The Grey Area Podcast is a CP Media Production hosted by Gabriel Smilovic, Stella Pyles, and Matthew Blackman - the generation that's figuring it out right now. Three people in their 20s at the intersection of creativity and business, navigating the ambiguous middle where nothing is certain and the rules are being rewritten.
Conversations here reside in the space between - not black, nor white. This isn't a self-help podcast. It's not a news show. It's for people building creative careers who haven't figured it out yet — and aren't pretending they have. We're not here to tell you what to think — we're here to open the floor.
The Grey Area Podcast is a CP Media Production hosted by Gabriel Smilovic, Stella Pyles, and Matthew Blackman - the generation that's figuring it out right now. Three people in their 20s at the intersection of creativity and business, navigating the ambiguous middle where nothing is certain and the rules are being rewritten.
Conversations here reside in the space between - not black, nor white. This isn't a self-help podcast. It's not a news show. It's for people building creative careers who haven't figured it out yet — and aren't pretending they have. We're not here to tell you what to think — we're here to open the floor.Listen on
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