Disclaimer: I started writing this a year ago, right after Taylor Swift dropped The Life of a Showgirl. It was also the middle of harvest and, to be frank, all the articles and social media hot takes I read about this release to prepare for this post were kind of bumming me out. But every month I revisit it when I’m feeling a bit tapped for ideas on what to write here, to see if I’m ready to tackle it again, and, long story short, I’m ready…?
Let me start by saying: I am not a music critic. I don’t really know how to talk about music in any coherent way. I tend to hyperfixate on a single song or album for weeks until I’m sick of it — when I first started this draft, I was listening to the metal cover of Golden from K-Pop Demon Hunters by Our Last Night on repeat. These days, it’s Kacey Musgraves’ Middle of Nowhere (more on that in a minute).
But I do notice things from a marketing perspective, and last fall I couldn’t stop thinking about Taylor Swift’s The Life of a Showgirl album release. Partly because I’m perpetually online, like any self-loathing social media “expert,” and partly because I LOVE paying attention to all kinds of marketing, even if it’s bad.
Now, before you close this article and unsubscribe because you're so fucking tired of hearing about TS, I beg you to stay with me. There’s a relevant point for wine brands here, I promise.
Marketing for this album was a bit misaligned with what we ended up getting
When Taylor started teasing The Life of a Showgirl, the visuals we saw were glamorous and theatrical. We saw Taylor Swift all done up in showgirl headdresses and rhinestones, which seemed to promise an album about the spectacle of fame and then some sad songs about what it’s really like when the makeup comes off.
Admittedly, the photographer in me was hoping for something very specific: Taylor’s initial marketing of the album put me in mind of Annie Leibovitz’s work with Las Vegas showgirls in the mid 90s. She photographed each dancer twice: once in full color, decked out in costumes, makeup, wigs, and headdresses, and once in a black-and-white portrait without any of it. Side by side, some of the women are almost unrecognizable. “The Showgirl” is a role they step into, and the person underneath is someone else entirely; I thought this album was going to be about that tension between the performance and the person.
However, what we actually got, both lyrically and sonically, was something different. Sure, there were nods to performers of yore (not necessarily showgirls), like The Jackson 5 and the Ronettes, being two that stood out to me. But, the songs weren’t really about being on the stage or even necessarily what happens behind the scenes, you know, showing the life of a showgirl. They instead seemed like disjointed storylines, alternately talking about how in love she is with her partner (and even his magical penis) and how someone talking shit about her makes her wet.
For the record, I identify as a Swiftie only on the high holidays. I show up for album releases, and I’ve drafted Taylor’s husband for my fantasy football team purely to trigger the toxic men in my league. And even with the disconnect, I really enjoyed this album. It’s not her best work, but it was fun and poppy, and a year later I’m still listening to (some of) the songs.
In any case, I think that’s one reason so many people, including some die-hard Swifties, were so critical of the album: the expectations the marketing set didn’t match what we ended up with.
Compare this with Kacey Musgraves’ Deeper Well rollout in 2024. From the first photos and single, we saw a clear folky, soft, grounded-in-nature aesthetic. The visuals matched the sound and the message, and fans connected immediately, because Kacey delivered on the promise she made us with her marketing.
Then, this spring, Kacey went and did it again with Middle of Nowhere, and even though this isn’t my favorite album of hers (Golden Hour is the best), it’s definitely one of my favorite album rollouts in recent memory.
In early March, billboards and posters started popping up in Nashville, Los Angeles, and New York with a photo of Kacey and a cheeky, retro message: “Dry Spell? Call for a real good time,” along with a phone number. If you called, you got a dial tone, then Kacey herself welcomed you to the middle of nowhere, plus a snippet of the new single. It had late-night hotline-ad energy, and I thought it was hilarious.
And once again, every single piece of the rollout matched the album. Sonically, it leans into Texas dancehall two-stepping. So, of course, the marketing was a bit more analog and a little kitschy (which I feel is classic Kacey).
And here is where our marketing lesson lies.
What This Looks Like in Wine
So many wineries do what Taylor did with The Life of a Showgirl rollout. They market one thing, then deliver a completely different experience to their customers.
Most often, it manifests as showing tasting experiences that don’t exist for those wineries, for example, people sipping wine in a vineyard at golden hour, when that winery doesn’t even have an estate vineyard, let alone a tasting that lasts long enough to see the sun set. Or a winery that’s appointment-only not being clear about that anywhere in their marketing. And I’ve even seen guests show up to events in high heels, only to find out there’s a walking tour of the vineyard, because no one told them what the day would actually involve.
So, something you can do this week to make sure you are actually delivering on what you promise:
Pull up your last nine Instagram posts, your website homepage, and/or your booking/reservation page. If someone walked into your tasting room tomorrow based only on those, would they feel like they were in the right place?
Ask a few recent visitors or club members what surprised them about visiting you. Surprises are great when they’re better than expected, but not so much in the other direction.
Look at your photos. If you find that your visuals aren’t aligned with the type of experience you actually offer, add “update my visual assets” to your to-do list (I know a photographer wink wink).
Consider adding a “what to expect” post to your social media that answers some FAQ about your tasting experience (tip: you can pin these posts to the top of your Instagram or save it as a Story Highlight).
When someone books a tasting or RSVPs for an event, set up an automated email that includes info like directions to your winery (especially if you’re out in the sticks), best places to park (if you don’t offer parking on-site or if parking can be a pain in the ass because you’re in the middle of the city), if you offer food or if they can bring a picnic, if you’re dog or kid friendly, if they should bring certain clothes for the weather, and even suggestions like “bring a camera so we can take a photo of you during your tasting!” Even if you include all that information in other places, it doesn’t hurt to reiterate certain points. We all know people don’t always fully read things.
The TL;DR
Taylor’s album still sold millions, of course. But most of us don’t (yet) have the luxury of built-in superfans like the Swifties. We have to work for that kind of trust and loyalty, and it starts with setting expectations that match what we deliver.
Be more like Kacey! Make a promise that’s true to who you are and deliver on it (also, while we’re at it, give people a way to stay in touch with you directly like she did with the phone number on the billboards).
What brand (wine or otherwise) do you think nails the match between its marketing and the real experience? Or the opposite? Let me know in the comments or reply to this email. I’d love to hear!
