The Crazy One

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The Crazy One

Stephen Gates

147 episodes

1 month ago

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 mom...

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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 mom...

Show more...

Episodes (20/147)

The Crazy One

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

In this episode of The Crazy One, Stephen Gates delves into Apple’s latest design overhaul: Liquid Glass. Unveiled at WWDC 2025, Liquid Glass marks Apple’s most significant UI transformation since iOS 7, introducing a translucent, dynamic interface across all devices. Stephen explores the strategic motivations behind this shift, the challenges it poses for accessibility, and its implications for designers and developers. Drawing parallels to past design philosophies and considering the broade...

2 months ago

14 minutes

The Crazy One

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 ow...

3 months ago

57 minutes

The Crazy One

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

In this fired-up episode of The Crazy One, Stephen Gates dives into the reality of the design industry today—where companies often fail to truly value creativity, even though it’s been proven to drive success. Drawing from his own experiences, Stephen reflects on the frustrations designers face as they see AI and platforms like Canva change the landscape. He challenges designers to stop being surprised by the lack of design appreciation in businesses and instead embrace this moment of disrupt...

3 months ago

17 minutes

The Crazy One

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

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—des...

4 months ago

19 minutes

The Crazy One

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

In this episode of The Crazy One, Stephen Gates shares the raw and honest story of his journey from working in agencies to building his own creative business. After being laid off for the third time, Stephen had to face the uncertainty of the future and decide whether to continue down the traditional career path or bet on himself. Through the highs and lows of freelancing, the challenges of entrepreneurship, and the lessons he learned along the way, Stephen talks about what it truly means to ...

4 months ago

23 minutes

The Crazy One

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

In this episode of The Crazy One, Stephen Gates shares his most valuable piece of advice for creative leaders: “You don’t need all the answers, you just need a plan.” Drawing from years of experience, Stephen discusses the common struggles people face when embarking on new challenges or career transitions and how to push through the uncertainty. He explains why creatives often get stuck in the cycle of overthinking, and how shifting your perspective to embrace a plan over perfection can help ...

6 months ago

11 minutes

The Crazy One

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

In The Crazy One Episode 135, Stephen Gates dives deep into a pressing topic in the creative industry today: “experience-ism.” As companies face economic downturns and shifting priorities, experience that once stood as an asset now feels like a liability. In this episode, Stephen reflects on the frustrations of senior creatives navigating the job market, where seasoned professionals find themselves sidelined for being “too experienced” or “too opinionated.” He explores how companies are shift...

7 months ago

10 minutes

The Crazy One

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

In episode 134 of The Crazy One, Stephen Gates dives into one of the most pressing challenges creatives face: navigating the job search. With many creatives either seeking new positions due to layoffs or dissatisfaction in their current roles, Stephen offers valuable insights on how to approach your portfolio, improve your job search strategy, and stand out in a competitive market. Drawing from his own experience and working as a hiring manager, he explains common portfolio mistakes, how to b...

8 months ago

34 minutes

The Crazy One

Ep 133 Career: How to get laid off

In this episode of The Crazy One, host Stephen Gates dives into a topic that’s all too familiar for many: getting laid off. With his personal experience of being laid off three times throughout his career, Stephen offers practical advice for those facing the uncertainty of potential job loss. He covers how to prepare for a layoff before it happens, the emotional rollercoaster of being let go, and the essential steps to take during and after the process. From understanding your severance packa...

9 months ago

18 minutes

The Crazy One

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

In this thought-provoking episode of The Crazy One, host Stephen Gates dives deep into the state of the creative industry in 2024. As the industry grapples with unprecedented layoffs and shifting dynamics, Stephen shares invaluable insights into the underlying factors driving these changes. He explores how economic pressures, evolving technologies, and changing consumer behaviors are reshaping the landscape for creative professionals. Listeners will gain practical strategies for navigating th...

9 months ago

15 minutes

The Crazy One

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

In episode 131 of The Crazy One podcast, Stephen Gates dives into one of the most common questions he encounters: “Should I start my own thing?” Drawing from his journey of leaving New York, starting his agency, and mentoring creatives, he explores the deeper challenges behind building a personal brand and finding fulfillment in a career. This episode challenges listeners to reflect on what truly makes them happy, what they want from their work, and how to break free from industry norms. Tune...

9 months ago

14 minutes

The Crazy One

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

In this long-awaited return to The Crazy One podcast, host Stephen Gates shares an honest and introspective look at his journey over the past year, from leaving New York and launching his own studio to grappling with burnout and rediscovering his passion. In this episode titled “Is This Thing Still On?”, he opens up about the emotional rollercoaster of going independent, confronting career disappointments, and evolving his relationship with the podcast. With a renewed focus on authenticity an...

9 months ago

9 minutes

The Crazy One

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

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, Product Development, and Career Growth. Tune in to discover actionable strategies to build a breakthrough career, from unlocking creative potential to thriving in an evolving industry. Stephen dives deep into essential career growth insights, with advice on navigating challenges, se...

1 year ago

56 minutes

The Crazy One

Ep 128 Career: How to start your studio or freelance business

With layoffs and uncertainty affecting creatives everywhere, many are asking: Is it time to go out on my own? In this episode of The Crazy One, Stephen Gates breaks down the critical questions to consider before diving into freelancing, consulting, or launching a business. Drawing from his own experience building a successful studio, Stephen explores essential steps to find clarity on the type of business that’s right for you, navigate challenges, and make informed decisions. Tune in for prac...

1 year ago

47 minutes

The Crazy One

Ep 127 Career: How to navigate and succeed in the era of defensive employment

In today’s career landscape, achieving success means taking on more responsibilities and adopting a proactive mindset—a shift Stephen Gates calls the “new era of defensive employment.” In this episode of The Crazy One, Stephen unpacks what’s driving this shift, how it impacts your career and leadership style, and the steps you need to thrive in this competitive environment. Get ready for actionable advice on standing out, adapting your approach, and navigating the evolving demands of today’s ...

2 years ago

45 minutes

The Crazy One

Ep 126 Career: Understanding the 2022 job market, a shift is coming

As the job market shifts from a fierce competition for talent to widespread layoffs and uncertainty, the creative industry faces both unprecedented challenges and new opportunities. In this episode of The Crazy One, Stephen Gates breaks down what’s fueling these changes in 2022, the major industry shifts he predicts in the coming years, and how these dynamics are influencing his own career path. Tune in for a candid discussion on navigating the evolving job landscape, positioning yourself for...

2 years ago

49 minutes

The Crazy One

Ep 125 Value of Design P3: Showing the value and impact of design

In the final episode of this 3-part series, Stephen Gates reveals actionable steps to help your team and organization truly appreciate the value of design. This episode of The Crazy One dives deep into how to conduct impactful design reviews, create a positive feedback culture, and use metrics and case studies to measure design’s influence. Whether you’re a design leader or a creative professional, learn how to communicate design’s business value effectively and elevate its role within your c...

2 years ago

36 minutes

The Crazy One

Ep 124 Value of Design P2: Creating demand for design

In this powerful second installment of the 3-part series, Stephen Gates dives deep into strategies for elevating design’s role within your team and company. In this episode of The Crazy One, he reveals how to create demand for design by building an effective action plan and implementing three key methodologies that position your team as essential contributors to business success. If you’re ready to make design a valued asset in your organization, tune in for actionable insights and practical ...

2 years ago

35 minutes

The Crazy One

Ep 123 Value of Design P1: Understanding the power and stigma of the word 'Design'

In the kickoff to this insightful 3-part series, Stephen Gates breaks down essential steps to help your team and company fully appreciate the value of design. In this episode of The Crazy One, Stephen explores how to shift perceptions of design from a “claim of ownership” to a powerful, strategic process. He dives into the importance of distinguishing creativity from execution and shares actionable methods for gathering data that can demonstrate design’s true impact. Perfect for creative lead...

3 years ago

35 minutes

The Crazy One

Ep 122 Career: How to decide if you should quit your job (or get a promotion)

In this insightful episode of The Crazy One, Stephen Gates tackles the challenging crossroads of career decisions, whether you’re aiming for a promotion or considering a job change. Both scenarios require clarity, self-reflection, and a strategic approach, and sometimes the biggest obstacle is recognizing your own blind spots. Stephen shares a straightforward process to help you assess the situation, identify critical issues, and have the honest conversations needed to find your path forward....

3 years ago

40 minutes