4.8 • 2K Ratings
🗓️ 5 May 2025
⏱️ 38 minutes
🧾️ Download transcript
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.
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0:00.0 | You're listening to the Why That Work podcast presented by storybrand.a.I. |
0:07.7 | If you've ever wondered why certain brands, trends, or cultural phenomena find success while others don't, |
0:12.6 | you're in the right place. Every week we unpack why something worked, then give you actionable insights that you can use in your own life. |
0:19.5 | Now let's dive in with your hosts, Donald |
0:21.3 | Miller and Kyle Reed. Don, did you know that you cannot have your bags travel for free anymore |
0:28.8 | on Southwest? Have you heard about this announcement? Yeah, I've heard a little bit about it. So back, |
0:33.0 | I mean, this is like recent back in March, they came out and the very thing they're known for, |
0:37.1 | their tagline |
0:37.8 | bags fly free one of their taglines what a what a great marketing message they're going back on |
0:43.3 | that now and it is causing a quite a conversation on the internet first of all let's acknowledge |
0:50.3 | something southwest probably has in in terms of airlines and maybe even large |
0:57.6 | corporations, the best messaging history. The way that they positioned, the differentiated |
1:04.4 | themselves from everybody charging for bags, what don't you like about bags? Why don't they |
1:09.0 | like bags? What's wrong with bags? Yeah. |
1:11.6 | Absolutely brilliant and memorable and playful and fun. |
1:15.6 | Absolutely incredible company in terms of getting a message out there and distilling it into soundbites, repeating those sound bites. |
1:25.6 | So this is an anomaly for them. And we'll get |
1:30.7 | into why it didn't work on the Why That Works podcast. We get into why it didn't work. |
1:36.0 | Let me just open up by saying I think it's a good time to buy stock in Southwest Airlines |
1:39.4 | potentially. But right. Yeah. You know, when you build your brand on discount prices and not |
1:47.3 | charging people for bags, it's a real challenge to kind of go back on that. And there's a way |
1:54.8 | to handle it. And I do think they didn't handle it perfectly, and there's still plenty of time. |
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