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.
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Contact path
Verified email
Booking probability
29%
Guest openness
Selective
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Signup to Generate a PitchThe 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.
The Grey Area is hosted by Gabriel Smilovic. The show has published 17 episodes to date.
Recent episodes include "1.17 - The End (For Now)" (29 June 2026, 38 minutes), "1.17 - The End (For Now)" (29 June 2026, 38 minutes), and "1.16 - The Performative Generation" (22 June 2026, 49 minutes).
The Grey Area publishes roughly weekly, with episodes averaging 43 minutes across 17 episodes.
Booking probability for The Grey Area is 29%, and the host is rated Selective on guests. The Grey Area requires a Pod Score of 80 or higher. The Grey Area's contact route on record: verified email.
Gabriel Smilovic hosts The Grey Area, a business podcast with 17 episodes published.
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Episode #17
<p>Episode 17 of The Grey Area Podcast, marks the end of Season 1. After 16 Episodes of exploring the spaces between black and white Gabe and Stella sit down for a final run of questions, picking apart the perils and...
Episode #17
Episode 17 of The Grey Area Podcast, marks the end of Season 1. After 16 Episodes of exploring the spaces between black and white Gabe and Stella sit down for a final run of questions, picking apart the perils and...
Episode #16
Episode 16 of The Grey Area Podcast, the second to last of Season 1, covers three questions that kept going deeper than expected. First: when is being selfish actually the right call — and when does it cross a line you...
Episode #16
<p>Episode 16 of The Grey Area Podcast, the second to last of Season 1, covers three questions that kept going deeper than expected. First: when is being selfish actually the right call — and when does it cross a line...
Episode #15
<p>Episode 15 of The Grey Area Podcast tackles three questions that sound simple until you try to answer them. Is loyalty overrated — and when does staying loyal actually hold you back? What are you bad at that you've...
Episode #14
<p>Episode 14 of The Grey Area begins with evermore pressing question of how to break free from the algorithm. Stella gave her number to a stranger on the A train. Gabe chased James Blake down the street with a receipt...
Episode #13
<p>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...
Episode #12
<p>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...
Episode #11
<p>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...
Episode #10
<p>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...
Episode #9
<p>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...
Episode #8
<p>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...
Episode #7
<p>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...
Episode #6
<p>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...
Episode #5
<p>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...
Episode #4
<p>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...
Episode #3
<p>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:</p>What does "authenticity" mean to you...
Episode #3
<p>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</p>
Episode #2
<p>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...
Episode #1
<p>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...
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