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!

Macrocast: This Jobs Report Isn't Fooling Around