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 design
• The real story behind Liquid Glass (and why most people missed it)
• How systems thinking reveals the future of AI integration
• What creative leaders can learn from Apple’s long game

This one might age like milk — or prove prophetic. Either way, it’s a must-listen.

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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.

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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 design industry right now, you haven’t been paying attention. From AI disruption to undervalued creativity to toxic corporate cultures, this episode breaks down the brutal reality creatives are living in—and why we need to stop hoping for change and start building it ourselves.

Stephen shares personal stories, historical receipts, and one hell of a perspective shift to challenge the narrative, reset expectations, and reframe what creative success looks like in 2025 and beyond.

In this episode, you’ll learn:

• Why most companies never really valued design—and probably never will
• The moment every designer faces that kills creative trust
• Why AI isn’t the end of creativity—it’s a shift in where the value lives
• What’s really behind career burnout, layoffs, and toxic work
• The dangerous comfort of comfort—and why it’s time to get uncomfortable
• Where bold creatives are finding better work, better clients, and more impact
• How to reframe your mindset, career path, and energy for what’s next

This is not a pity party. It’s a gut check. A rally cry. A reminder that we’ve always had the power—we just have to stop pretending we don’t.

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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 YouTube), but to unpack the bigger picture. What’s really at stake for creatives? How do we separate innovation from imitation? And what do we do in a world where originality is being overshadowed by copy-paste culture?

Stephen draws on decades of watching tech waves come and go—desktop publishing, digital design, NFTs—and argues why AI is different, but our response doesn’t have to be passive. This is a call to action for real creativity, deeper thinking, and sharper storytelling.

In this episode, you’ll learn:

• Why we’re entering an era of creatives vs. copycats—and how to make sure you’re on the right side
• What AI can do well, and where it still fails miserably
• The real threat: companies and creatives who treat design as disposable
• How to use AI as a tool without losing your original voice
• Why comfort is the enemy of relevance in a rapidly changing industry

This isn’t a hype session or a panic spiral—it’s a push to engage, experiment, and show the industry why creativity still matters.

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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 the truth behind the leap: the real risks, the unexpected wins, and the power in finally doing work that feels like yours.

This episode isn’t a glorified founder story. It’s a raw, honest reflection on what happens when you walk away from the broken systems and build something with your own two hands. From burnout and layoffs to reclaiming creativity and control, Stephen breaks down the mindset shifts and hard-earned lessons that have shaped his journey—and why this moment might be your moment too.

You’ll learn:

• Why chasing validation in job interviews is a losing game

• How Stephen reframed fear into freedom (and how you can too)

• The unsexy business truths no one tells you about freelancing

• Why knowing what you actually want is everything

• The emotional weight of owning your failures—and your wins

• How to recognize when it’s time to stop surviving and start building

This is not about overnight success.

It’s about reclaiming your voice, your value, and your vision. Bet on yourself—just make sure you’re ready to do the work.

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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 uncertainty: you don’t need the answer—you need a plan. When the road ahead feels overwhelming, this mindset shift can change everything. It’s not about having it all figured out. It’s about starting. This one’s for anyone who’s paralyzed by “what if” and needs a push to take the first step.

Stephen unpacks:

• Why the beginning is always the hardest part
• How creatives can reframe life and leadership as design challenges
• The trap of overpreparing and waiting for certainty
• Why great leaders lead with a plan, not perfect answers
• How a bias toward action builds real confidence
• The difference between stupid and crazy (hint: one of them has a plan)

Stop waiting for permission. Start building your plan. Then take the leap.

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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 holds us back—and the simple mindset shift that sets real leaders apart. It’s the advice he gives in almost every mentoring session. The one thing that changes everything.

Because leadership isn’t about knowing it all. It’s about starting before you do.

In this episode, you’ll learn:

• Why most people get stuck at the starting line—and how to break through it
• The difference between a plan and an answer (and why that matters)
• How to apply design thinking to your career and decisions
• What a “bias towards action” really looks like in practice
• Why confidence comes after the leap—not before it

This one’s for anyone standing at the edge, waiting for certainty. Spoiler: it’s not coming. But you are more ready than you think.

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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 portfolios, what they’re looking for, and why most creatives are missing the mark. Whether you’re in the middle of a job search, feeling stuck in a bad gig, or just want your work to tell a better story, this episode is your wake-up call — and your roadmap.

You’ll learn:

• Why your portfolio is a crystal ball for hiring managers — and how they read it
• The red flags that instantly kill your chances (sliders, typos, and broken links, anyone?)
• How to structure your book like a story — not a slideshow
• The myth of “they’ll connect the dots” and why it’s killing your chances
• What it really means to treat your portfolio like a design problem
• How to get better feedback — and why most people don’t
• The hard truth: results take real work, not shortcuts

This is the feedback you wish you’d get — and the challenge to do something about it.

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