Hi, friends.
Today we're talking Taylor Swift. I'm thrilllled to welcome Cincinnati-based strategy director and consultant Anna Wilhelm for a chat and chew on what Taylor does better than most consumer brands out there, among other zealous digressions. Anna's led client accounts from Brooks to Chobani, and I've run product partnerships with brands from BAGGU to Lucasfilm. Like Taylor, we have feelings. Visuals ft. Phoebe's SNL guitar smash and a few supporting actors from DALL•E.
Read through for insights on:
- Taylor and strategy: How does a vibe evolve? And achieve radical commercial success while remaining true?
- Taylor and the sound of the female psyche: How does she and Jack articulate the emotion of the present moment through sound?
- Taylor as productivity instigator: Why are we so productive with Taylor+Jack on loop?
- Taylor's lineage: What has she done for the creative industry?
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Vicky: HI HALLO. How is your mind feeling today
Anna: Good, feeling good, sharp + the appropriate accentuating glowy fog lol. Yours?
Vicky: Also strangely good, hoping for some semblance of flow state. Woke up early to noodle on a brand marketing piece inspired by all the tech layoffs
Anna: Oh INTERESTING. Yeah I’d love to hear your thoughts on all that
Vicky: oh BOY do i have strong thoughts on it all. though for now - T SWISS. how many thoughts we have on taytay?
Anna: SWISSSS LOL
Vicky: Ok Capitalized Vicky coming into motion. Vicky: Let's talk about Taylor and strategy. What does she teach us about strategy? About how a vibe evolves? And achieve radical commercial success while remaining true to its core?
Starter food for thought from Chuck Klosterman for GQ in 2015:
"Like almost all famous people, Swift has two ways of speaking. The first is the way she talks when she’s actively shaping the interview—optimistic, animated, and seemingly rehearsed (even when that’s impossible). The second is the way she talks when she cares less about the way the words are presented and more about the message itself (chin slightly down, brow slightly furrowed, timbre slightly deeper). The first way is how she talks when she’s on television; the second is unequivocal and less animatronic. But she oscillates between the two styles fluidly, because either (a) this dissonance is less intentional than it appears or (b) she can tell I’m considerably more interested in anything delivered in the second style."
Anna: Love this question. First I'll clarify for me, strategy is something applied to branding and advertising (from creative concepts to media placements). What has always made me a great strategist is my ability to mash up seemingly disparate concepts, eras, etc. and find the cultural insight. Sometimes I've felt bad about it, like it's cheating, or like someone smarter probably thought of it before me. But Taylor's approach to eras, and her different approaches to songwriting and production per era, make me (perhaps an equally self-conscious person) feel way more comfortable just working with what inspires me in a moment, or era, and not feeling bad about it.
I also love how she as an artist draws inspiration from her personal life, from the internet, from age-old tales, etc. all as equally valid sources of inspiration. And with a mind that's as able to inspire a (almost literal) cult following as it is to put together some of the most unique arena shows of modern music history. That's how the best creative work seems to be developed these days—being able to do "it all," but only when "all" is the sum of everything you really enjoy or are great at.
Vicky: And I think that's the interesting thing about how Taylor's become a cultural artifact. She doesn't quite disappear from The Culture and let the inspiration come, she LIVES it, she IS the culture, whether organically, arguably masochistically, etc. Her lovers (fans) love it, yet the ambivalent audiences are confounded because she's also smart and sexy. She's not calculating; she's just performing vulnerability while retaining a tight rein on her narrative (compared to performers like, say, Britney).
Which is kind of like…what companies with good branding & marketing do? Good* meaning highly visible and revenue generating.
Chuck Klosterman speaks to this in GQ too: "Even within the most high-minded considerations of Swift’s music, there is inevitably some analysis (or speculation) about her personal life. She’s an utterly credible musician who is consumed as a tabloid personality. Very often (and not without justification), that binary is attributed to ingrained biases against female performers. But it’s more complicated than that. Swift writes about her life so directly that the listener is forced to think about her persona in order to fully appreciate what she’s doing creatively. This is her greatest power: an ability to combine her art and her life so profoundly that both spheres become more interesting to everyone, regardless of their emotional investment in either."
Anna: I love that quote! The lack of separation is what I think makes Midnights such an interesting album. Her best songs are about her. Whether the real "her," or the publicly viewed "her," or a mix.
Re: her not being calculating—I agree to a point. She confesses her own calculations on Midnights and takes blame for many of her own issues on it, too. But I think you're right in that it's from a very raw/vulnerable place for her. She's self-conscious, wracked with rejection, tired of pleasing no one because she's trying to please everyone. So it makes her calculating, in a strategic way. "I'm only cryptic and Machiavellian because I care."
Vicky: And it's that very genuine "tired of pleasing" that ushers in what I think is her most effortless album yet (with the exception of folklore/evermore era).
Midnights is not about reinvention or innovation; it’s about refinement. By jamming with Jack Antonoff for over a decade. Greasing the keys until the stories slide right off, collecting even the debris into effortless sonic tension.
Anna: One reviewer wrote that the album felt like stepping into the cave of the female psyche—filled with the synth, echoes, and other-worldy shimmer that exist there—and I thought that was so incredibly accurate.
And with the common theme of the album not being an era, but rather a state of mind, I am thinking her approach to eras is going to shift pretty significantly and I'm excited to see what future records from her look and sound like.
Vicky: This is very interesting in context of brand strategy. Because when I look at many of the most visible companies in branding (specific to the cool kid DTC environment in NYC) — many look like they have the same soul, which is when they start to look bland. There is no proprietary edge showing, just prosaic ads who've all adopted the same visual packaging and tone of voice.
Anna: Oh, absolutely. A favorite on that: Bloomberg's "Welcome to Your Bland New World". Even with it shifting into the gen Z edge of the same phenomenon, millennial pink is replaced with neon yellows and purples. Sans-serif replaced with serif. It's the same formula, just shifting ingredients.
Vicky: It's like what used to be exciting turns into comfort food. The aspiration of DTC brands is wholesale retail, mass markets, and making it big with B2B accounts. The road to exit is becoming the next gen of P&G, Kraft Heinz, etc. They don't lead the marketing with this business strategy, and it's not a bad thing, but what usually happens is scale thrives is weird dies. They need to lean into this choice if they make it, rather than try to sustain their weird in a way that falls short for everyone.
When I worked in consumer marketing, one of the biggest messaging challenges we faced was in concurrently selling to B2C and B2B. You're hesitant that mass market affiliation might dilute your brand capital, yet you need their partnership for investor-friendly growth. (It's possible to do it all but few can do it deftly.)
Anna: It also becomes a signal: "this is safe to consume." Your reputation won't be damaged. You are not (directly) lining the pockets of an 80-year-old white man who voted for Trump.
Vicky: Yet in a way, for brands to cash in on mass appeal…that means they must grow beyond partisan lines and race and class divides. Has Taylor somehow cracked this, in strangely a similar way as Bob Dylan? As critics Sam Sanders and Ann Powers talk about via Vulture/NPR pod.
Anna: Oooh, great question. I agree—the blanding trend is very classist and often leans white-washed. I think music has a natural leg-up on branding thanks to the storytelling element, but yes, the NPR podcast hit the nail on the head by describing her as a confessional singer-songwriter from the lineage of Carole King with a little Bob Dylan (plus Joni Mitchell aspirations). I do think core human emotions transcend time, race, and class. And she does tap into those. It just depends on if people are willing to believe her and connect there.
Vicky: I want to go back to the sound of the female psyche that you brought up. How do Taylor and Jack craft their world through sound?
They use instrumentation to amplify the tension and release in the storytelling. Lots of restraint in how she sings, stepwise melodies, pulsing tension in the bass, synth that floods the background with this ambient anchoring feel. It's very much a vibe of the times—how the kids today feel, reflected aurally.
Anna: I made my boyfriend (an indie-rock songwriter and musician) listen to Snow on the Beach and tell me what he thought. He called out the bass line in it—how unlike the natural mechanics of stringed instruments, the production of this bass doesn't let it taper off. It just keeps on its tonal pulsing on repeat. He pointed out how this sound is far more common in hip-hop, rap, or pop/R&B productions, versus the airy indie production of the rest of the song—like how the voices are breathy, the drums sound 2 rooms away, etc. That tension between those two sonic universes is something you can either love or hate. It can scratch an itch you never knew your brain had, or may you feel really cozy.
But I remember you talking about the gentle, dreamy pulsation of that song, so of course I thought of you!
Vicky: Hehe ty for the thought. Mildly related further listening - in Mark Ronsons's Watch the Sound on Apple TV, there's a great episode on the emotional effect of reverb (they start with Amy Winehouse as example).
The sound leads to our next topic on Taylor Swift as productivity instigator - why are we so productive with Taylor & Jack on loop?
Anna: My gosh. It is the most true. I could conquer the world if Jack's production was my backing track. But Taylor+Jack, that's a story I fall into and don't want to crawl out of. I'd say I actually can't work as well to their collaborations as I can to his other work. When Out of the Woods or Archer or Betty come on, I kind of drop everything and end up fully in their universe for a few minutes.
For me, it's how he works with rhythm in the music. Whether the actual drums and percussion, or with the unusual speaking patterns borrowing more from rap/hip-hop than traditional pop.
Vicky: "if Jack's production was my backing track…" what a call out! In a world where general listeners normally aren't aware of the producers. Fueled by Taylor, Jack's an interesting case study of Producer as Personality (outside music insiders).
Now stepping back - on how the music stimulates us intellectually - my thesis: It's like British writer Matt Ridley's "idea sex," but applied to music. He gave a Ted Talk (which I haven't seen) on "how, throughout history, the engine of human progress has been the meeting and mating of ideas to make new ideas — basically ideas having sex with each other. The sophistication of the modern world lies not in individual intelligence or imagination, he says, instead it's a collective enterprise. That means it's not important how clever individuals are; what really matters is how smart the collective brain is."
And my unscientific, unrevolutionary supporting point: there's something in their sonic construction that somehow fires up our neurons in tune with our emotions while listening. This is not new news but the scale that they've amassed is the point to note. Like it's not an indie band inspiring their niche arty fanbase, but it's mainstream artists stimulating the creativity of genpop (short for general population, borrowing from market researchers).
She's shepherded the next gen of singer songwriters, e.g. Olivia Rodrigo. This is more powerful than her individual legacy and all the top 10 hits and records she's broken herself. She's set the collective heart in motion.
Now to her lineage: What has she done for the creative industry?
Anna: Olivia Rodrigo is a perfect example of a cultural artifact derivative of Taylor's legacy. Millennials loved Olivia's record (and did so as silently as possible so Gen Zs wouldn't turn on her lol). Although she writes about high school love, her songs took me back to a bad breakup in my mid-20s. As a confessional singer-songwriter—falling in line with Taylor—she is writing about human emotions in a way that is borderline embarrassing in its transparency. Yeah, other people did it before Taylor. But taking it this mass, an artist known around the world by all generations, I do think this is the next level. I just hope the future of music can retain the honesty here.
Vicky: I still can't get into Olivia. I even watched her Disney+ documentary to try to endear herself to me (lol). It's thrilling that this lineage has become so expansive I can find elements that aren't for me. (While appreciating other parts, e.g. ABGs now have another Asian celebrity as an option to dress up as for Halloween)
Anna: Oh wow—see, I know nothing about her and like it like that. I don't want to see any of her Disney+ content. I just want to listen to her album track by track chronologically. 😅
But yes. We love that for the ABGs.
Vicky: Taylor has enabled expression to so many—let's call it—underrepresented talents that we don't have to be everyone's uncritical cheerleader.
Anna: Agree re: lineage and its expansiveness. If Olivia Rodrigo isn't for you, Phoebe Bridgers probably is. Etc. etc. Choose your own adventure.
Vicky: Reminds me of Indonesian singer-songwriter NIKI. I describe her latest breakup album as Taylor Swift meets Phoebe Bridgers, or a more R&B Olivia Rodrigo.
Anna: Yes, I love NIKI's stuff!! You described that perfectly.
Another interesting thing about Taylor's trajectory (and I may have to fact check myself on this) is that post-Scooter Braun, I'm not sure she's had any male openers for her shows. Her upcoming Eras tour has a roster of 8 or so openers (2 per show) and all are women acts.
Her way of bringing artists into the limelight reminds me a lot of Brandi Carlile championing female artists, particularly queer ones, and giving them the acclaim they deserve in a way that is so blatant and intentional that the Taylor/Brandi fans are fully on board and instantly obsessed with whatever new talent she brings before them.
Vicky: OMG re: Brandi Carlile - yes. I just read a Variety piece on how she supported Marcus Mumford with his new solo album on the themes of being sexually assaulted as a kid.
Anna: Uh, yeah, speaking of confessional songwriting. That record was so good, and her closer with him was INCREDIBLE.
Vicky: Also like, I don't follow him but that collab was unexpected. Same with some of Taylor's collabs (e.g. how that Future track happened).
Anna: Yeah, and I love collabs because they reveal artists' sources of inspiration listeners may not be aware of. Same goes with covers.
Vicky: Bringing it back to the creative economy: there are so many brands and creators so busy trying to become the cultural elite that they miss out on the fact that the magic is in the already but not yet. The magic is already here, in them, their unseen inspirations, invisible aspirations.
Anna: Yes, everything behind the curtain. I was a passive fan of Taylor Swift, might even say fully neutral to her, before I saw the Miss Americana documentary. Seeing artists experience inspiration, seeing them drop the mask of perfection, that to me is the magic. Watching people be incredibly good at something they love, working to continually hone their skill, always revisiting their favorite inspirations to keep their creative tank filled. That's where they become artists whose art I'll invest in. It's not cultural capital. It's being human.
Vicky: and there we have it
Anna: THERE WE HAVE IT
Feature image: Taylor Swift / Beth Garrabrant
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