Brands That "Lose Their Cool" Might Actually Be Winning Long-Term (A Contrarian View)
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Today's issue tackles something that might make you uncomfortable. I will argue that brands going through a "not cool anymore" phase might be positioning themselves for stronger long-term success than those staying trendy.
I know, I know. This sounds counterintuitive. But hear me out.
Most brand builders I've worked with in the last twenty years panic when they see negative buzz about their brand "losing its edge" or "not being cool anymore." They immediately pivot, chase new trends, or completely overhaul their strategy. Rejuvenation needs lead to chasing Gen-Z or soon Gen Alpha, but it may be a downward spiral. I wrote a previous article about this some time ago:
Chris Maffeo
But what if that's precisely the wrong move? What if these brands are actually in a healthier position than we think?
Some days ago, I read a post on LinkedIn about how Guinness is now "back" after years of losing its cool.
In my view, Guinness had always been cool for its core drinkers, and they were never alienated. The brand wasn't "not cool anymore" for them—it was still relevant, authentic, and connected to their identity.
The "not cool anymore" noise came from newer customers recruited during a trendy moment, but didn't connect with what Guinness represents. They were attracted to the fad, not the brand.
So here's my controversial take: Guinness wasn't failing - it was succeeding at shedding the wrong customers.
The Pattern I Keep Seeing
This happens everywhere in our industry. Brands chase quick growth by appealing to casual consumers during cultural moments, then seem to "fail" when the trend passes. But they haven't really failed - they just prioritized rapid expansion over steady, authentic growth.
Many brands want to expand their consumption occasions and recruit new consumers into the categories, but they often should just keep doing what they are doing instead of getting bored and seeing the grass greener on the other side.
Think about it like this: when a brand goes through this cycle, it's like playing Monopoly and landing on the wrong square. You have to step back and rebuild from your solid foundation. But that foundation was never actually damaged.
The brands that survive these cycles might ,be stronger because they've learned to focus on depth over breadth.
Why This Might Be a Winning Strategy
Here's what I'm starting to believe: it's better to be deeply relevant to fewer people than superficially appealing to everyone.
When I work with brands now, I ask them: "If this cultural moment disappeared tomorrow, would your core customers still care about your brand?"
The brands that can answer "yes" seem to weather trend cycles better. They might look like they're "losing" in the short term, but they're building something more sustainable.
They're building anti-fragile brand equity.
And here's what really gets me: once you identify what you truly stand for, maybe brands should just be left alone to be consistent. Instead of jumping left and right, chasing every opportunity, what if the winning move is simply sticking to your guns?
There's something almost sick about the way we chase growth at the expense of brand longevity. We see a quarterly dip and panic. We see a competitor getting buzz and immediately pivot. We see a cultural moment and think we have to participate.
But what if that constant movement is exactly what's killing long-term brand value? What if the brands that seem to "lose their cool" are actually just refusing to participate in this exhausting dance?
But Am I Wrong?
Look, I'm not saying every brand losing its cool is winning. Some brands genuinely lose their way and never recover. The difference might be whether they have that solid foundation to return to.
Maybe the real question is: Are you building for trends or longevity?
The brands that seem to "lose their cool" and then come back stronger understand something crucial: sustainable cool comes from being genuinely relevant to the right people, not temporarily appealing to everyone.
But I want to challenge this thinking with you. Maybe I'm romanticizing what's actually just poor brand management. Perhaps some brands really do need to stay trendy to survive.
What Do You Think?
Here's what I'm curious about: In your experience, have you seen brands that went through "not cool anymore" phases actually come back stronger?
Or am I completely off base here? Do the brands that stay consistently trendy win in the long term?
I'm genuinely torn on this. On one hand, I've seen brands like Guinness prove that returning to your authentic core can be a winning strategy. On the other hand, I've seen plenty of brands that lost their cool and never recovered.
Maybe the key isn't whether you lose your cool, but whether you have something authentic to return to.
What's your take? Have you built a brand that went through this cycle? Are you currently in a "not cool anymore" phase and wondering if you should pivot or stay the course?
I'm especially curious to hear from anyone who's been on both sides - brands that successfully navigated this transition and brands that didn't.
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This is exactly the kind of topic I want to debate with you. Drop a comment below and tell me:
- Have you seen brands successfully navigate a "not cool anymore" phase?
- Are you currently facing this challenge with your own brand?
- Do you think I'm completely wrong about this?
Start the conversation 👇 I read every comment and I'm genuinely curious about your perspective.
Chris Maffeo
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