The Grey Area

1.11 - Don't Read My Substack

Episode 11 of The Grey Area Podcast goes somewhere the show hasn't been before. It starts with a simple question — do you have a personal rule that would sound ridiculous out loud? — and the answers prove that everyone's a little unhinged when nobody's watching. Then Gabe goes back to 13, when a diagnosis with ulcerative colitis took him off the tennis court, put him on steroids, and sent him into eighth grade hoping nobody would notice. He talks about self-advocacy, Big Pharma, and what he wishes he could tell that kid now. Stella goes back to age two — not to say anything, just to sit with the version of herself that was still being built. They get into what they'd create if nobody ever saw it — Gabe reveals he's writing a fiction novel under a pen name, Stella wants to write things she can't attach her name to, and Matt says music. And then the whole thing turns into a books episode: The Fountainhead, Huckleberry Finn during cancel culture, a Czech word that means "the rosy light of the sun on mountains," and why English may never be enough. The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

1.10 - Bobby Flay Was Right

In Episode 10 of The Grey Area Podcast, Gabe, Stella, and Matt start with a question they weren't ready for: what would your 18-year-old self be confused by about your life right now? Gabe thought he'd be working in finance. Stella thought she'd be a parent by 27. Neither of them thinks their teenage selves would have even been friends with who they are today. Then they get into the social norms they've quietly let go of — Gabe is six weeks without drinking, Stella stopped feeling guilty about leaving early, and Matt's girlfriend taught him something at the Botanical Gardens he won't forget. They close on focus, discipline, and a lesson Gabe picked up at dinner with Bobby Flay: the time to start something new is when what you're doing is working, not when it starts to fall off. The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

1.9 - Are We Really Supposed to Be Here?

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.

1.8 - Hawaiian Punch and Hidden Skills

Episode 8 of the Grey Area Podcast pulls from two recent Substacks that Gabe and Stella wrote for The Creative Pragmatist and turns them into a conversation. First: stealth skills — the ones you collect without knowing it. Stella traces hers back to a Hawaiian Punch heist she pulled on her grandmother at five years old. Gabe traces his to a restaurant kitchen and the systems that taught him how to think under pressure. Then they get into the wave — the idea that when your life shifts overnight, it was never actually overnight. It was building beneath the surface for years, and the break is just the arrival. And they close on manifestation — not the kind where you stare in a mirror and hope. The kind where you train your mind to give yourself a real shot, and then trust that what comes is what's supposed to. The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

1.7 - Proactively Reacting

In Episode 7 of The Grey Area, Gabe and Stella dive into the difference between being proactive and being reactive — and why the best moments of their careers have come from the chaos they didn't plan for, including a runway show where the collection truck tipped over on the highway four hours before showtime. Then they talk about what "right" actually feels like — Gabe tells the story of an RV trip through Joshua Tree that changed his entire career path, and why the signs you're looking for aren't always written in the sky. They close with the question they keep circling back to: what would you do if money, society, and industry pressure weren't in the way? Turns out they both want the same thing — peace, nature, and the work they love without the noise. The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.