The Crazy One

Stephen Gates
  • 4.9 (416)
  • Design
  • Updated Biweekly

The Crazy One is an award-winning podcast for creatives, leaders, and anyone who refuses to settle. Hosted by renowned designer and global design leader Stephen Gates, this show delivers unfiltered honesty, actionable insights, and hard-won wisdom to help you grow your creativity, lead with confidence, and build a meaningful career. With over two decades leading world-class design teams at companies like InVision, Citi, Starwood Hotels, WW, and McCann Erickson, Stephen has built brands and digital experiences for clients including Disney, American Airlines, W Hotels, Verizon, Acura, and more — work that’s earned over 150 international awards and has been featured by Apple in 10 keynotes, 4 commercials, and the Human Interface Guidelines. Now as the founder of CRZY, an independent strategy and design studio, he’s helping companies find bold new visions for their brands, experiences, and creative futures. Through The Crazy One, he shares everything he’s learned along the way — from integrating behavioral science with human-centered design to navigating imposter syndrome to building a career and creative life on your own terms. With over 100 episodes and a loyal global audience, The Crazy One has been named: • Webby Award Honoree for Best Technology Podcast • #1 Podcast by Inside Design, HOW Design Live, and Springboard • 5-star rated across every iTunes Store worldwide This is more than a design podcast. It’s a wake-up call. A masterclass. A real-talk guide for finding your voice, owning your crazy, and changing the game. No BS. No buzzwords. Just real insights from someone who’s been there.

  1. 1h ago

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

    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 actually looks like once execution stops being what makes your team valuable. Not whether to adopt AI — that conversation is over. The real question is whether you're willing to redefine what your team produces, who's actually equipped for that shift, and what you're going to do about the people who aren't. Stephen breaks down the five things that now separate teams that matter from teams that don't — judgment, taste, context, connection, and the often-overlooked skill of actually training and stewarding the models your team uses. He also lays out three things every leader needs to do this week, starting with an honest audit of what your team really produces. Stephen anchors this in years spent studying how the world's best chefs build teams and develop talent from scratch, and in building CRZY Design around the idea that headcount has never equaled quality. Both point to the same lesson: technique can be taught, and increasingly, AI can do it. Palette can't be bought, faked, or automated. This one's for any creative leader who suspects their org chart, job descriptions, or own habits are still optimized for a team that no longer exists, and who'd rather hear that now than find out later. In this episode: Why "is AI going to take my job?" is the wrong question for leaders to be askingThe five things that actually separate teams now: judgment, taste, context, connection, and systems stewardshipWhy headcount-based, execution-mapped org charts are solving the wrong problemThe "palette" lesson from the world's best kitchens — and why hiring on technique alone is a long-term liabilityA three-step leadership audit: what AI could do, what AI could assist with, and what only your team can do — and why that ratio is the most important number you're not looking atThe hardest truth in the episode: AI didn't take anyone's job — it gave executives a way to finally act on what they already believedSend us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    35 min

  2. May 21

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

    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 waiting for a retrospective. In this episode, Stephen argues that pre-mortems aren't a luxury anymore. They're the only way responsible teams can keep pace with and scale AI-assisted work. He walks through six questions every team needs to answer before any project where AI touches the workflow — not as a checklist, but as the conversation you have before the pressure hits. Stephen anchors the argument in a core frustration he's named on the show before: most teams are in the consequence business without ever acting like it. From the Pokémon Go failures to the output-obsessed cultures that celebrate shipping as success, the episode makes the case that individually good decisions can still add up to collectively disastrous outcomes. This one is for any team using AI in their work who hasn't yet had a real conversation about what happens when it goes wrong. In this episode: Why the post-mortem era is over — and what has to replace itThe six pre-mortem questions every AI-assisted project needs answered upfrontHow to map the blast radius before you're in a war room during a crisisThe headline test: writing the failure story before the project startsWhy agreeing on non-negotiables is the easy part — and holding to them under pressure is the real workWhy AI is a culture problem, not a technology problem — and why this episode is the proofSend us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    26 min

  3. May 14

    Ep 145 Creativity: Stop Asking AI to Agree With You

    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, not a better prompt library — a completely different posture. Most people learned to use AI the same way they use Google: ask for an output, take the answer, move on. That habit is quietly eroding your thinking. AI is trained to be helpful, which means it's trained to agree. If you keep asking it questions you already know the answer to, all you're getting back is your own assumptions dressed up in more confident language. The fix is treating AI like a sparring partner, not an assistant. That means building the discipline to ask the questions you don't want to ask — the ones that pressure-test your ideas before the room does it for you. In this episode: Why AI's confidence is the dangerous part — it states wrong things with the same authority as right onesThe sparring partner model: how to shift your posture toward AI so you get genuinely better thinking out of itFour types of challenge prompts: failure, assumption exposure, data validity, and pre-mortem — and exactly how to use each oneWhy most people skip this step (hint: it's not because they don't know how)A 15-minute exercise you can do today with any idea you're working onThe people who will be dangerous with AI aren't the ones using the best tools. They're the ones asking the best questions. This episode is for anyone who wants to be one of them. Send us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    17 min

  4. May 6

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

    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 wave of creative layoffs — and why asking "is AI going to take my job?" is already the wrong question. Using a framework he's shared with teams and mentors for over fifteen years, Stephen maps out the four quadrants that determine your real value inside any organization: human-led execution, AI-led execution, AI-amplified strategy, and human-led strategy — and explains exactly why where you sit in that grid matters more than any performance review, portfolio, or title ever will. He also goes back to the moment that changed how he thinks about all of this: getting laid off while his work was running globally in an Apple commercial. Good work isn't enough. Great execution isn't enough. What matters is what gets said about you when you're not in the room. This is an uncomfortable episode — but it's the one you need to hear. In this episode: Why AI gave companies cover fire, not a new ideaThe four-quadrant framework for understanding how leadership actually thinks about your roleWhy "do you value design?" is the wrong question to ask your leadershipThe question that will actually tell you where you standWhat to do if you don't like the answerSend us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    23 min

  5. Apr 29

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

    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, your workflow, or whether you've got the right prompts. The problem is culture — and most leaders are treating it like a hardware upgrade. In this episode, Stephen breaks down the most urgent shifts he's seeing inside teams and companies right now: why being "output drunk" is quietly destroying careers and brands, why speed is the new debt, why the organizational pyramid is flipping — and what happens to an entire generation of creative professionals if we don't start solving for that. He also gets into the practical: what you review in meetings, how you hire, what you kill, and why pre-mortems need to replace post-mortems before it's too late. This isn't a conversation about AI tools. It's a conversation about survival — and it's one almost nobody is having yet. Send us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    23 min

  6. Apr 15

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

    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 Noise — the growing layer of almost-right work that's quietly eroding quality standards, collapsing accountability, and making it harder than ever to defend the value of real expertise. He breaks down how it's breaking organizations, why experts are partly to blame, and what you can actually do about it. Send us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    21 min

  7. 06/18/2025

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

    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 its core. From WWDC buzz to Liquid Glass backlash, this one’s not about UI drama — it’s about system strategy. Stephen unpacks Apple’s latest moves through a deeper lens: unified design, AI readiness, and what it really takes to build future-proof experiences. Because this moment isn’t just about skeuomorphism making a comeback. It’s about Apple quietly setting the stage for a smarter, more integrated creative ecosystem — and what that signals for the rest of us. Why design decisions at Apple are never just about designThe real story behind Liquid Glass (and why most people missed it)How systems thinking reveals the future of AI integrationWhat creative leaders can learn from Apple’s long gameThis one might age like milk — or prove prophetic. Either way, it’s a must-listen. Send us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    14 min

  8. 05/07/2025

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

    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 into the tough decisions that led him to bet on himself. He talks about embracing the fear of failure, navigating imposter syndrome, and overcoming the challenges of creative work in a corporate culture that doesn’t always value it. Whether you’re considering going out on your own, struggling with self-doubt, or just looking for a way to reconnect with your creative passions, Stephen’s story offers valuable insights and actionable advice to help you take the next step in your career. Tune in for a candid conversation about the challenges and rewards of betting on yourself and turning your passion into your profession. Send us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook

    57 min
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Trailer

4.9
out of 5
416 Ratings

About

The Crazy One is an award-winning podcast for creatives, leaders, and anyone who refuses to settle. Hosted by renowned designer and global design leader Stephen Gates, this show delivers unfiltered honesty, actionable insights, and hard-won wisdom to help you grow your creativity, lead with confidence, and build a meaningful career. With over two decades leading world-class design teams at companies like InVision, Citi, Starwood Hotels, WW, and McCann Erickson, Stephen has built brands and digital experiences for clients including Disney, American Airlines, W Hotels, Verizon, Acura, and more — work that’s earned over 150 international awards and has been featured by Apple in 10 keynotes, 4 commercials, and the Human Interface Guidelines. Now as the founder of CRZY, an independent strategy and design studio, he’s helping companies find bold new visions for their brands, experiences, and creative futures. Through The Crazy One, he shares everything he’s learned along the way — from integrating behavioral science with human-centered design to navigating imposter syndrome to building a career and creative life on your own terms. With over 100 episodes and a loyal global audience, The Crazy One has been named: • Webby Award Honoree for Best Technology Podcast • #1 Podcast by Inside Design, HOW Design Live, and Springboard • 5-star rated across every iTunes Store worldwide This is more than a design podcast. It’s a wake-up call. A masterclass. A real-talk guide for finding your voice, owning your crazy, and changing the game. No BS. No buzzwords. Just real insights from someone who’s been there.

Information

  • Creator
    Stephen Gates
  • Years Active
    2016 - 2026
  • Episodes
    153
  • Rating
    Explicit
  • Copyright
    © 2026 @2015 SDGates Creative
  • Show Website
    The Crazy One

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