#18: Southwest—The Genius of ‘Bags Fly Free’ and What Happened When It Changed
Southwest Airlines built one of the strongest brands in the world by doing one thing better than almost anyone: clear, clever messaging that made customers feel like family. “Bags fly free” was more than a tagline. It was a promise that set them apart from every other airline. But when they recently backtracked on that core message, the backlash was instant. In a world where loyalty is fragile and expectations are sky-high, even the best brands can stumble if they don’t communicate the right way. So what happens when a company known for brilliant messaging gets it wrong? In this week’s episode, Don and Kyle unpack the marketing brilliance that made Southwest an iconic brand and why their latest messaging misstep is such a big deal. They reveal how Southwest’s playful, people-first branding created an unbeatable bond with customers, and how this new shift risks breaking that trust. You'll learn what Southwest could have done differently, why your messaging must evolve without abandoning what made you great, and how to communicate tough changes without losing customer loyalty. Tune in to find out how even a beloved brand can slip and how you can avoid making the same mistake. -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!
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#17: Annoying Ads—The Dumbest Campaigns That Won Your Attention and Made Millions
Most people try to make their marketing polished, clever, or inspirational. But in the end, clarity beats creativity every time. In fact, some of the most “annoying” ads in history made hundreds of millions of dollars simply because they were impossible to ignore. They weren’t beautiful, they weren’t clever, but they were unforgettable. So why do so many businesses avoid this approach? Because we assume our customers want sophistication, when what they really need is a message that’s crystal clear and easy to remember. If your ad gets ignored, it doesn’t matter how gorgeous it is. In this week’s episode, hosts Donald Miller and Kyle Reed discuss the genius behind annoying marketing campaigns like HeadOn, Chia Pet, and the George Foreman Grill. You’ll learn why these seemingly ridiculous ads worked, how they used repetition and simplicity to dominate attention, and what you can take away to sharpen your own message. Tune in to learn how to make your marketing stick no matter how simple (or obnoxious) it may seem. -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!
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#16: Airbnb—The Brilliant Strategy Behind Their New Messaging Campaign
If your marketing isn’t working, it’s probably because you’re not talking about the right problem. Most businesses struggle to identify the most compelling issue their customer is trying to solve. They either talk about too many things or pick a problem that’s too vague. When that happens, customers stop listening. But when you finally address the problem that makes your customers say “yep, that’s me!”, sales start to climb. That's what Airbnb just nailed with their new messaging campaign. So, how do you figure out the exact problem your business solves in a way that drives real results? In this episode, Don and Kyle break down Airbnb’s latest messaging campaign and why it hits the mark so effectively. They unpack the brilliance behind how Airbnb redefined the problem it solves and how you can apply the same strategy to your own business. You’ll learn a simple way to clarify the problem your customer actually cares about and how to build an effective messaging campaign around it. Listen in for strategic tips on how to get sharper messaging and more customer engagement. -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazonor wherever you buy books!
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#15: Morning Routines—The NEW Way To Create A Morning Routine In 2025
If you followed every piece of advice out there about your ideal morning routine, you'd probably spend eight hours every day doing mindfulness excercises and supplements and journaling and workouts and cold plunges and more. But morning routines can be both easy AND effective if you identify the right mission for your life. In this episode, Kyle Reed and Donald Miller break down a new way to approach your morning routine—one that actually fits the demands of 2025. Whether you’re a high-performing entrepreneur, a working parent, or just trying to get your act together before 9am, this conversation is packed with practical strategies, unexpected insights, and a fresh mindset shift. You’ll learn: • Why most morning routines fail (and what to do instead) • How to reverse-engineer your day for better mornings • The role of intention, simplicity, and rhythm in a sustainable routine • What Kyle and Don are doing differently this year—and why it’s working If you’ve struggled with consistency, motivation, or just hate mornings altogether, this episode will help you build a routine that serves your real life—not some influencer’s highlight reel. -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books! If you're tired of feeling unproductive and unmotivated, get clarity on your life goals and supercharge your productivity by visiting HeroOnAMission.com for your free planner!
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#14: Simplicity—Why a “Less Is More” Approach Can Make Anything More Effective
Most businesses, brands, and even thought leaders make the same mistake: they overcomplicate things. The more complex something is, the harder it is for people to understand—and if they don’t understand, they don’t engage. Whether you’re trying to grow a business, capture attention, or lead a movement, clarity is your greatest asset. That’s why we’re shaking things up this week with a very special recap episode! We’re revisiting some of the most valuable insights from past episodes—all centered around one powerful theme: simplicity. Don and Kyle explore how frameworks, storytelling, and clear communication can help you find clarity, make better decisions, and connect to more people. Tune in to discover why the most successful brands, leaders, and ideas all follow one golden rule: keep it simple. -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!
About Why That Worked – Presented by StoryBrand.ai
Welcome to Why That Worked – Presented by StoryBrand.ai. Have you ever wondered why some brands, trends, or products become massive successes while others fade away? That’s exactly what this podcast explores. Hosted by Donald Miller, creator of the StoryBrand Framework, and co-hosted by Kyle Reed, each episode dives into the strategies behind the world’s biggest wins, breaking them down into clear, actionable insights you can use to create your own success.
Discover how to craft clear and effective messaging that works for your business at StoryBrand.ai.
Listen to Why That Worked – Presented by StoryBrand.ai, Right About Now with Ryan Alford and many other podcasts from around the world with the radio.net app
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