Not Just for Swifties: The Business Strategy Behind the Buzz

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No, we’re not about to drop a surprise album, but we are building a hospitality brand that lasts.

When people think about hospitality, they don’t usually think about Taylor Swift. But maybe they should.

Her Eras Tour wasn’t just a concert, it was a masterclass in brand building, storytelling, and direct connection. And at Smart Pineapple, we see more in common with her strategy than you might expect.

We Build Loyalty That Lasts

Taylor’s fanbase spans generations because she speaks to emotion, not just transactions. At Smart Pineapple, we take a similar approach. Yes, we teach you how to use AI, automate your guest emails, and boost your direct bookings, but underneath all of that is something more powerful: purpose-driven marketing.

We help small hotels and vacation rental owners build something they own, clear messaging, strong community, and authentic brand voice—so guests keep coming back (and telling their friends).

We Help You Own Your Audience

Taylor Swift didn’t leave her visibility in the hands of algorithms, she built direct channels: newsletters, pop-ups, and a digital infrastructure that she controls.

We do the same. From email marketing strategies to community engagement, we’re not here to get you likes, we’re here to help you grow bookings, guest relationships, and long-term impact.

We Believe in Reinvention Without Losing Our Roots

Swift’s strength is in evolving while staying unmistakably her. We get that. Our founder, Kay Walten, has 35+ years in international hospitality and tourism, but she’s never stopped learning, testing, and evolving. From underwater exploration to AI education, Smart Pineapple blends deep roots with new tools.

That’s why we teach. That’s why we build community. And that’s why we believe small hospitality businesses can absolutely compete in a world of OTAs, flashy startups, and overwhelming tech—because they have something better: real stories and real connection.

Our Version of the Eras Tour?

It’s called legacy.

We’re not here for the quick win. We’re helping clients build systems, skills, and visibility they can carry forward for years to come—tools may change, but clarity and consistency never go out of style.

Final Note

We may not sell out stadiums. But if you’re a small property with big dreams, and you’re tired of relying on third parties to do your marketing for you—we’d love to help you build something that lasts.

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This Is Our Reputation Era. We Keep It Chill, But We’re Choosy. Get on the List.

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