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The Crazy One

Arts

The Crazy One

Stephen Gates

Ep 148 Creativity: 7 Years, 3 Buzzwords, 2 Studies, and 1 Constant Problem

June 25, 2026 8:00pm 36 min

In 2019, I helped run the largest study ever done on the relationship between design and business performance. We found that the vast majority of companies were stuck, full of creative potential that they couldn't conver...

Leadership: Judgment, Taste, and the Five Things AI Still Can't Touch

June 17, 2026 8:00pm 34 min

Your team's value used to come from how fast and how well they could execute. That formula is broken, and most leaders are still managing teams built for jobs that no longer exist.This episode is about what leadership ac...

Ep 146 AI: Premortems, Because A.I. Won't Wait for a Retrospective

May 20, 2026 8:00pm 26 min

The "ship it, fix it later" playbook was already broken. AI just made it catastrophic. Post-mortems assume you have time to observe, adjust, and course correct. AI has collapsed those timelines, and the damage isn't wait...

Ep 145 Creativity: Stop Asking AI to Agree With You

May 13, 2026 8:00pm 17 min

You've turned the most powerful thinking tool in history into a yes-machine — and it's making your ideas weaker without you even realizing it.This episode is about a fundamental shift in how you use AI. Not a new tool, n...

Ep 144 AI: Your Company Decided Your Value Before AI Existed

May 05, 2026 7:00pm 22 min

AI didn't build the case to replace you. It just gave companies the tool to finally act on a decision they'd already made.In this episode, Stephen Gates gets brutally honest about what's actually happening underneath the...

Ep 143 AI: AI Isn't a Tool Problem. It's a Culture Problem.

April 28, 2026 8:00pm 23 min

Four years into running CRZY, Stephen has watched AI go from an interesting experiment to an organizational crisis that almost nobody is naming correctly. The problem isn't which model you're using. It's not your stack, ...

Ep 142 AI: The hidden cost of plausible, almost-right work

April 14, 2026 8:00pm 20 min

AI and cheap tools have given everyone the ability to produce work that looks professional, sounds credible, and feels like the real thing. The problem? It isn't. In this episode, Stephen introduces the term Plausible No...

Ep 141 Design: A bigger strategy behind Apple’s Liquid Glass?

June 17, 2025 8:00pm 14 min

Stephen finally breaks the seal on AI — not with a prompt tutorial or workflow breakdown (he’s got a YouTube video for that), but with a deeper dive into the real conversation: how AI is shaking the creative industry to ...

Ep 140 Keynote: 'Bet on Yourself" BeMore Festival 2025

May 06, 2025 8:00pm 57 min

In this episode of The Crazy One, Stephen Gates shares the lessons learned from his journey of leaving corporate America to start his own agency. With over 20 years of experience across industries, Stephen dives deep int...

Ep 139 Career: The Hard Truth About Creativity’s Role in Business Today (and Yesterday)

April 25, 2025 8:00pm 17 min

This one’s part wake-up call, part battle cry. After too many sleepless nights and too many same-old conversations, Stephen Gates climbs up on the soapbox to call out the hard truth: if you’re shocked by the state of the...

Ep 138 Creativity: AI Isn’t the Enemy. Complacency Is.

April 08, 2025 8:00pm 19 min

The AI hype train is moving fast—and it’s already crashing into our creative industry. In this episode, Stephen finally wades into the AI conversation, not to break down tools or workflows (you’ll find that on his YouTub...

Ep 137 Career: The Pros and Cons of Going Out on Your Own

April 02, 2025 8:00pm 23 min

After decades inside the system—agencies, in-house, and everything in between—Stephen Gates made the leap. No roadmap. No safety net. Just a decision to bet on himself. Three years later, he’s pulling back the curtain on...

Ep 136 Career: Overcoming Fear and Insecurity: Why You Need a Plan, Not the Answers

January 30, 2025 8:00pm 11 min

You’re stuck. Spinning in circles. Overthinking every move. Sound familiar? In this episode, Stephen breaks down the single most powerful piece of advice he gives to creatives, leaders, and anyone facing a moment of unce...

Ep 135 Career: The Hidden Problem of ‘Experience-ism’ in Creative Careers

January 23, 2025 8:00pm 10 min

When the stakes are high—new job, big idea, career leap—most of us freeze. We stall, waiting for the “right” moment, the perfect answer, the foolproof plan. But in this episode, Stephen shares the raw truth behind what h...

Ep 134 Career: Tough Love for Your Portfolio: Stand Out or Stay Stuck

November 28, 2024 6:00pm 34 min

Most portfolios don’t get rejected for lack of talent. They get rejected because they’re saying the wrong things — or nothing at all. In this episode, Stephen pulls back the curtain on how hiring managers actually review...

Ep 133 Career: How to get laid off

November 12, 2024 9:00pm 18 min

Let’s be real — layoffs suck. Whether you saw it coming or it hit you out of nowhere, it’s personal, painful, and way too common in today’s industry. In this episode, Stephen breaks down everything he’s learned from bein...

Ep 132 Career: Navigating the Mess: Insights into the 2024 Job Market

November 06, 2024 9:00pm 15 min

Let’s be honest—this industry is a mess right now. Layoffs are everywhere, leadership roles are disappearing, and even the best of the best are struggling to get a callback. In this episode, Stephen Gates tackles one of ...

Ep 130: Ending the hiatus. Is this thing still on?

November 03, 2024 7:00pm 9 min

After a year-long silence, The Crazy One is back — but not the same. In this raw return, Stephen opens up about the real reasons behind the show’s hiatus, the toll of being laid off (again), and how starting his own stud...

Ep 131 Career: What's stopping you from going out on your own?!?

November 03, 2024 7:00pm 14 min

After 13 months away, the mic is back on—and we’re starting exactly where too many of us are stuck. In this raw and real return, Stephen unpacks the one conversation that’s been rising to the surface in every mentoring s...

Ep 129 Keynote: BeMore Festival 2023 - How to build a breakthrough career

October 01, 2023 8:00pm 56 min

In this powerful episode of The Crazy One podcast, Stephen Gates shares his standout keynote from the 2023 BeMore Festival, the ultimate 24-hour global super conference featuring over 100 top voices in Design, AI, Produc...

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