#18: Southwest—The Genius of ‘Bags Fly Free’ and What Happened When It Changed
Release Date: 05/05/2025
The StoryBrand Podcast
Get free marketing videos from Don every week at WeeklySoundbite.com Leadership success often hinges on a trait many people misunderstand: self-awareness. In today's fast-paced world, leaders are surrounded by noise: social media flattery, AI-generated validation, and constant feedback loops that create more confusion than clarity. And while confidence is essential, when it crosses into narcissism, the fallout can be devastating. Think Enron, Lehman Brothers, or any organization led by someone blind to their own flaws. Narcissistic leaders may get results, but the cost is often burnout,...
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Get free marketing videos from Don every week at WeeklySoundbite.com Most businesses struggle to explain what they do in a way that actually gets people interested. You tweak your website copy, add more content, and keep pitching your product, but the reaction is lukewarm at best. Why? Because you’re missing the most critical part of a messaging strategy, what Donald Miller calls the “5 front steps.” Think of your brand as a house. Without these front steps, you're essentially asking customers to leap onto your front porch with no ladder in sight. It's a recipe for lost sales. So...
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Get free marketing videos from Don every week at WeeklySoundbite.com Most taglines don’t work. They sound clever, but when customers see them, nothing happens. No interest, no sales, just crickets. That’s because most taglines are vague, confusing, or forgettable. And when people have to burn mental calories trying to figure out what your business actually does, they’ll just move on to the next option. If your tagline isn’t clearly offering something your customer wants, it’s not helping you. It’s costing you. So how do you make sure your tagline actually drives results?...
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Get free marketing videos from Don every week at WeeklySoundbite.com Businesses are burning cash on Facebook ads that just don’t work, and it’s not because of the algorithm. The real problem? Most companies are leading with clever headlines and flashy visuals instead of clear, curiosity-driven messaging. When your potential customer sees your ad, they’re not thinking about your brand, they’re thinking about their own survival. If your ad doesn’t speak to that in the first two seconds, you’ve already lost them. With ad costs going up and results going down, the stakes...
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Get free marketing videos from Don every week at WeeklySoundbite.com Most business owners dread being asked, “So, what do you do?” Not because they don’t know, but because they don’t know how to explain it without rambling. When you stumble through your business model or every service you offer, people glaze over. That moment is your shot to spark curiosity and build value, but if you blow it, you lose potential opportunities. Whether you’re networking at a conference, pitching a client, or updating your website, you need one sentence that makes people lean in and say, “Tell...
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Get free marketing videos from Don every week at WeeklySoundbite.com Welcome to the first episode of The StoryBrand Podcast (formerly Why That Worked), where we’re doubling down on what actually grows businesses: clear messaging. Most business owners are too close to their own work to explain it clearly. They tweak and refine, but your customers still don’t “get it.” That’s why we’re hitting reset on this podcast and going back to the foundation of great messaging. In this premier episode, Kyle Reed and Donald Miller kick things off with a full masterclass on...
info_outlineSouthwest 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.
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