The Grey Area

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• 1.13 - For the Time Being 01.06.2026 57min

  Episode 13 of The Grey Area Podcast opens with bits — the dumb, ridiculous little jokes you carry through life that remind you nothing is as serious as it feels. Matt's dad pretends to die every time someone blows out birthday candles. Stella used to threaten to shave her head and leave the bangs. Gabe does crossovers on strangers walking down the sidewalk. Then the conversation goes somewhere unexpected — Gabe tells the story of a trip to Austin two years ago that nobody ever saw. A podcast filmed in a garden where they forgot to account for the sun. A country singer's backyard session. A vintage shop visit staged like a movie scene. It never came out, but looking back, it was the first draft of everything CP Media builds now. That leads into the real conversation: getting off the starting block. Gabe spent two and a half years building a business plan for an app that never launched. At 12, he and Matt tried to start a clothing line and Amy told them to stop planning and just go to CustomInk and order 10 shirts. Stella auditioned for Joffrey Ballet knowing something inside her said it wasn't the path. And Matt pulls a folded Star Wars manifesto out of his wallet that ends with one word: try. They close on risk — what makes you take one, what keeps you frozen, and whether the scariest thing is the leap or never knowing what was on the other side. New episodes every Monday. Part of the Almost Reckless universe from CP Media.
• 1.12 - Send the Text 26.05.2026 34min

  Episode 12 of The Grey Area starts with a question that sounds simple and isn't: what's the difference between something that's valuable and something that's just hard to get? Gabe lays out the trap — you see someone with the car, the watch, the life, and you assume those things are worth chasing because they're difficult to obtain. Stella pushes back hard: some of the most valuable things in her life showed up by accident. Matt lands it somewhere in the middle — value might find you by chance, but keeping it takes everything you've got. Then they put their phones on the table and text someone they've been thinking about, right there on the mic. Gabe can't find Scout's number but says it anyway. Stella tells the story of meeting her best friend Anna at an ex-boyfriend's prom and then running into her on a college campus a year later. And the whole thing spirals into Buddhism, attachment, Stephen Colbert telling Anderson Cooper that suffering is a gift, and whether you can feel everything and hold nothing at the same time. New episodes every Monday. Part of the Almost Reckless universe from CP Media.
• 1.11 - Don't Read My Substack 18.05.2026 51min

  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 11.05.2026 35min

  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? 04.05.2026 41min

  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 27.04.2026 41min

  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 20.04.2026 43min

  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.
• 1.6 - Looking in The Wrong Mirror 13.04.2026 52min

  In Episode 6 of The Grey Area Podcast, Gabe and Stella get into what happens when you're putting all your energy into fixing the wrong thing — going to the gym twice a day when the real problem is how you see yourself, spiraling over a typo in an email to 200 people when no one's dying, and the feedback loops that have been telling you you're not enough since you were a kid. Then they build their Mentor Man — the idea that your mentor isn't one person but a composite, assembled from everyone who shaped how you think, feel, trust your gut, and keep moving. Head, heart, gut, arms, legs — each one a different person. 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.
• 1.5 - The Frontal Lobe Has Arrived 06.04.2026 42min

  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 5, Gabe and Stella get into what creativity actually means when you strip away the performance of it, why the friendships that survive your mid-20s are the ones built on honesty instead of agreement, and what happens when your priorities flip and you barely recognize who you were six months ago. The frontal lobe at 25 is real, FOMO is a phase, and the best show they've been to all year was the one where nobody reached for their phone. New episodes every Monday. Part of the Almost Reckless universe from CP Media.
• 1.4 - Assume the Best, Clear the Noise 30.03.2026 41min

  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 4, Gabe and Stella unpack a failed college startup and what it taught about drive, why assuming the best in people is harder than it sounds (especially if you grew up with three sisters or a middle school that destroyed you), and the mental clarity problem nobody talks about — when the thing you're doing to decompress is actually making it worse. Plus: ego deaths, people pleasing, contract negotiations, and the TikTok algorithm you built brick by brick. A CP Media production, born from the world of Almost Reckless. New episodes every Monday.
• 1.3 - Growth in Discomfort 23.03.2026 35min

  Episode Three of the Grey Area Podcast, hosted by Stella Pyles, Gabriel Smilovic, and Matthew Blackman, looks to answer three new questions this week through the Gen-Z lens:What does "authenticity" mean to you? How does it appear, or not appear, in your daily life?Describe your relationship with "discomfort" - elaborate.What are the driving forces in your life that tempt you to take risks? What are the forces that discourage you to take risks?
• 1.2 - Who is Your Hero? 16.03.2026 38min

  Episode Two of the Grey Area Podcast, hosted by Stella Pyles, Gabriel Smilovic, and Matthew Blackman, looks to answer three new questions this week through the Gen-Z lens - 1) Identify a list of individuals that you admire - style, career, character. What are the specific attributes that you admire? Is there a throughline between them? 2) Which to you is more important: experience, or common sense? 3) When you get dressed, how do you want to feel? Is there a connection between this craving and other aspects of your life?
• 1.1 - Welcome to The Grey Area 09.03.2026 51min

  Welcome to The Grey Area Podcast hosted by Stella Pyles and Gabriel Smilovic. On this week's episode, we introduce the catalyst for TGA – "Almost Reckless: A Creative and Pragmatic Approach to Taking Risks" by Amy Smilovic. Riffing off the concepts and principles outlined in the book, we dive into a list of questions that prompt us to think beyond the black and white and embrace ambiguity. We certainly don't have all the answers, and we won't always agree – but we do know that when you open up the floor to good, honest discourse...good conversations happen.