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.

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.

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.

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:

1. What does "authenticity" mean to you? How does it appear, or not appear, in your daily life?
2. Describe your relationship with "discomfort" - elaborate.
3. What are the driving forces in your life that tempt you to take risks? What are the forces that discourage you to take risks?

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?

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.