Episodios

  • Is OpenAI Building the iPhone of AI?

    Is OpenAI Building the iPhone of AI?
    May 23 2025
    What happens when the world's best designer teams up with the most powerful AI company? We’re about to find out. OpenAI just announced a partnership with legendary Apple designer Jony Ive, and it could signal a shift as big as the launch of the iPhone. I break down why this matters, what it means for the future of devices, and why Apple should be nervous. But that’s just one topic from this week’s “Junk Drawer” episode. I’m also diving into two major branding redos - HBO’s backpedal from “Max” and Jaguar’s quiet retreat from a futuristic rebrand that didn’t land. And finally, I unpack two brutally honest CEO letters about AI adoption, employee expectations, and the wave of AI-driven layoffs already underway. In this episode, I cover:
    • What OpenAI and Jony Ive are building, and why it could be revolutionary
    • Why HBO is putting “Max” in reverse and re-embracing its heritage brand
    • What Jaguar’s branding mess reveals about mismatched audiences and agencies
    • A look at AI-first and AI-forward companies (and why it matters)
    • How CEOs at Shopify and Fiverr are preparing for an AI-dominated future
    • Why “being the AI person” at your company might save your job
    • A listener's question about freelance client ghosting, and my real-world advice

    This episode covers a lot—from branding failures to bold new tech—but all of it speaks to where marketing, business, and creativity are heading. Links:
    • Sam & Jony introduce io
    • HBO Max is Back
    • Episode 38 - Walmart & Jaguar’s Logo Redesigns: Pointless or Brilliant?
    • A Letter from Shopify CEO Tobi Lutke
    • A Letter from Fiverr CEO Micha Kaufman

    Do you have a question or just need to vent about your marketing frustrations? Send it to fbymarketing@skyeline.com, and I might just answer it in a future episode. FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    19 m
  • No Targeting, No Creative, No Strategy?! Meta’s Shocking AI Plan

    No Targeting, No Creative, No Strategy?! Meta’s Shocking AI Plan
    May 16 2025
    In this episode, I’m breaking down something Mark Zuckerberg said that should’ve shocked every marketer, but barely anyone’s talking about it. He just laid out a vision for AI-powered advertising that doesn’t need strategy, creative, or even an understanding of your audience. I unpack what he said, why it’s a huge deal for marketers, and what we can do to prepare. You’ll learn:
    • What Zuckerberg actually said in his recent interview about AI-driven advertising
    • The rise of “black box marketing,” and why it’s more dangerous than helpful
    • Why letting platforms control your brand is a fast path to irrelevance
    • The hidden risks behind Meta’s “just connect your bank account” promise
    • How ad costs will skyrocket, and why most brands won’t be ready
    • What a future of third-party AI-powered ad platforms might look like
    • How to build your own transparent, brand-safe black box using today’s AI tools
    • Why strategy, creativity, and knowing your customer still matter, maybe more than ever

    Zuckerberg might be right about where things are headed, but that doesn’t mean it’s good for your brand, your strategy, or your business. Here’s the link to the full Stratechery interview with Mark Zuckerberg: https://stratechery.com/2025/an-interview-with-meta-ceo-mark-zuckerberg-about-ai-and-the-evolution-of-social-media/ Do you have a question or just need to vent about your marketing frustrations? Send it to fbymarketing@skyeline.com, and I might just answer it in a future episode. FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    8 m
  • Why The Ice Bucket Challenge Went Viral (And Came Back)

    Why The Ice Bucket Challenge Went Viral (And Came Back)
    May 9 2025
    In this episode, I’m breaking down one of the most iconic charity marketing campaigns of all time and why nearly every attempt to copy it has failed. We’ll revisit the Ice Bucket Challenge, explore the emotional and social dynamics that made it explode, and look at its 2025 reboot aimed at mental health. I share lessons for marketers and non-profits who want to build real momentum without resorting to gimmicks. In this episode, I cover:
    • Why the original Ice Bucket Challenge really went viral
    • The difference between a viral stunt and an authentic movement
    • What made the 2025 “Speak Your Mind” reboot catch on
    • Why most copycat campaigns fall flat (think Twizzlers, rice buckets, and chicken wings, to name a few)
    • How to build something small but meaningful inside your own community
    • Why you can’t manufacture a viral moment, but you can engineer the conditions for one

    If you’ve ever thought, “Let’s just do something like the Ice Bucket Challenge,” this episode will help you rethink your approach. Do you have a question or just need to vent about your marketing frustrations? Send it to fbymarketing@skyeline.com, and I might just answer it in a future episode. FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    13 m
  • Should You Let Clients Know You’re Using AI? | Listener Questions

    Should You Let Clients Know You’re Using AI? | Listener Questions
    May 2 2025
    AI is changing everything - but how much should you say about using it? In this episode, I’m answering listener questions about the messy world of marketing with AI: ethical dilemmas, burnout, client fears, and the pressure to be perfect (and fast). From freelancers losing work to AI to internal teams unsure how to position their AI-assisted work, this episode digs into the unspoken tension many marketers are feeling right now and how to handle it. In this episode, I cover:
    • Should you disclose when you use AI for your work?
    • Why “AI saves time” can backfire fast
    • How to position yourself as a strategist (even if you’re not one)
    • When perfectionism helps, and when it’s just procrastination
    • Why some clients are firing their freelancers for AI, and how to respond
    • How to ride a viral moment for all its worth

    If you’re feeling undervalued, overworked, or unsure how to keep up with the AI wave, this one’s for you. Do you have a marketing question or just need to vent about your frustrations? Send it to fbymarketing@skyeline.com, and I might just answer it in a future episode. FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    17 m
  • Why Most Podcasts Fail: And What I Learned After 50 Episodes

    Why Most Podcasts Fail: And What I Learned After 50 Episodes
    Apr 25 2025
    Most podcasts don’t make it past episode three. 90% of the rest quit before episode 20. So, how did Frustrated By Your Marketing? hit episode 50? And what did I learn along the way? This isn’t a victory lap; it’s a breakdown of what it takes to create consistent content, why YouTube nearly killed the show, and how podcasting became my personal testing lab for marketing experiments, AI tools, and new platforms. In this episode, I cover:
    • Why 99% of podcasts fail - and how to avoid the same fate
    • The mindset shift that helped me push through the dip
    • What I learned the hard way about YouTube, Google Ads, and Spotify Ads
    • Why content creators need a single platform to call home
    • How podcasting helped me level up in AI, networking, and strategy
    • Why having a pet project might be the best move for your marketing career

    This episode is for anyone who feels burnt out, stuck, or unsure whether their content is working. I’ve put in 500 hours on this show, and I’m just getting started. If you’re building something that feels hard, that’s not failure. It’s just the middle of the story. FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    15 m
  • Retirement Is a Marketing Scam: AI Will Make It Worse

    Retirement Is a Marketing Scam: AI Will Make It Worse
    Apr 18 2025
    We’ve all been told that retirement is the goal - the reward after decades of hard work. Save up, slow down, and finally enjoy life. But what if that entire idea is just a well-packaged marketing campaign? In this episode, I break down why the concept of retirement was invented, how it’s been sold to us for decades, and why the rise of AI is only making that pressure worse. From Otto von Bismarck to Bill Gates, from “Golden Years” brochures to the push to “make room” for Gen Alpha, retirement isn’t what you think it is. And if you’re in marketing, you should know better. In this episode, I cover:
    • Why retirement was never about freedom - it was about control
    • How AI will accelerate the pressure to step aside
    • Why stacked 401(k)s, dream vacations, and pickleball don’t always deliver the joy they promise
    • What Bill Gates and Dick Van Dyke understand about purpose
    • Why marketers should be the least likely to fall for retirement messaging
    • How to start designing your future with intention

    This isn’t about working forever. It’s about choosing fulfillment now, and staying sharp in a world that keeps trying to sell you a future at the expense of today. FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    12 m
  • Is WordPress Falling Apart? Inside the CEO Power Struggle

    Is WordPress Falling Apart? Inside the CEO Power Struggle
    Apr 11 2025
    Most people think WordPress is a stable, community-driven platform. And for the most part, it is. But behind the scenes, a bitter power struggle is threatening everything that makes it great. In this episode, I break down the escalating feud between Matt Mullenweg, the CEO of Automattic, and WP Engine, a billion-dollar WordPress hosting company. From plugin takeovers to legal battles, the WordPress ecosystem is caught in a fight over power, money, and the future of open source. This drama could reshape how over 43% of the web is built. In this episode, I cover:
    • The September speech that ignited the feud between Matt and WP Engine
    • Why WordPress trademarks and plugin control are suddenly under fire
    • Why the WordPress community is losing trust in its founder
    • How WordPress leaders like Sé Reed and Joost de Valk are standing up for change
    • My predictions for how WordPress could fork into multiple platforms

    Whether you're a developer, designer, or just someone with a WordPress site, this matters. Because when one person controls a platform that powers nearly half the web, the fallout affects us all. LINKS:
    • Episode 37 - TikTok, Trump & Social Media’s Future in 2025

    FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    16 m
  • AI Images Changed Everything: The Creative Economy Is Just Beginning

    AI Images Changed Everything: The Creative Economy Is Just Beginning
    Apr 4 2025
    Most people think AI is killing creativity. I think it’s doing the opposite. In this episode, I explore ChatGPT's new image generation features and why it’s sparking panic in the design world. From Studio Ghibli-style portraits to South Park selfies, the line between inspiration and copyright violation is getting blurry fast. But here’s the twist: I believe we’re entering a new golden age of creativity. In this episode, I break down:
    • What’s actually possible with the new AI image tools (and what blew my mind)
    • Why the Studio Ghibli backlash is bigger than just style theft
    • The four types of copyright risk when using AI-generated art
    • Why creativity still matters—and might matter more than ever
    • How the “final economy” could be built on stories, art, and human expression

    If you’ve been worried AI is replacing creative work, this episode offers a different perspective. The tools are powerful—but the story is still ours to tell. LINKS:
    • Episode 10 - Why We Love WordPress

    FRUSTRATED BY YOUR MARKETING? is hosted by Jim DeMicco and presented by SkyeLine Studio. LET’S CONNECT: LinkedIn | Website | YouTube | Facebook | Instagram | TikTok | Twitter/X
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    18 m
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