I'm not a businessman, I'm a business, man
Let me handle my business, damn
While it might be Jay-Z’s most iconic line, it was delivered as a sort of premonition of the future for the latter half of the most iconic power couple in commercial music history. But Jay-Z’s business, man, spawned from leveraging off of astounding levels of creative excellence — while many of his lyrics contain references to his entrepreneurial spirit and hustle, music came first, then business. His pivot to commercially mainstream music was almost a farewell tour, a celebration of how far he had come before he moved on to bigger and greater things. While we got the perennial modern New York anthem Empire State of Mind, which still closes down Manhattan bars to this day (and is a favorite of mine to do at karaoke with random Japanese strangers in Osaka), Watch the Throne was the last gasp of a king willingly leaving his throne, like Magnus abdicating his World Champion title. Music officially went on the back shelf, and Kanye was handed the keys to the music kingdom.
Being good in business is the most fascinating kind of art. Making money is art and working is art and good business is the best art.
The prior, quintessential Andy Warhol quote is exemplified by none other than Taylor Swift, whose business acumen is inextricable from her main product — her music. If Jay-Z and Kanye represent the Jobsian ethos of obsession with creativity to the brink of self destruction, Taylor is the Tim Cook-esque successor, evidenced by her transformation from Kanye antic-adjacent and producer of songs for high school girls dreaming about their prom dress to such a commercial force that even the Fed is writing about her commercial impact, to the point where her Eras tour is genuinely being debated as an inflationary force. Much like I wax poetic about how it’s impossible that a business as large as Apple can be so incredibly well run, it’s unfathomable to me how incredible of an operation TSwift’s entire career has been.
If I consider myself a New Yorker, I have to consider Taylor one too, considering we both moved out there in 2014. By then, she was already one of the most prominent commercial artists, but as someone whose music taste developed from blogs and boards and The Pirate Bay, I didn’t have much exposure beyond that award show incident. That became decidedly impossible after 1989 released, with Welcome to New York essentially becoming co-opted by incoming Columbia and NYU freshmen and the perpetual inflow of transplants. The endless debates of whether Taylor was country or not were over — much like a nascent startup moves to the Bay or a budding financier takes a summer analyst role on the Street, the tonal and regional shift was decidedly an “I’m a business, man” move, because that’s where the money is. It also helps that 9 out of the 13 tracks were (and are) absolute smash hits, achieving the increasingly scarce distinction of being a pop album that’s an actual album, and an exquisitely produced and shaped one at that. It’s rare that the first iteration of a formula pans out so well — her “formula but not formulaic” approach to album production was already a 10/10 out of the gate. 1989 contains none of the manic brilliance of My Beautiful Dark Twisted Fantasy or the schizophrenic perfectionism of Pet Sounds, but it’s filled with the meticulous intensity of the zero-inventory global supply chain. You will get your new Taylor banger when you want it with the exact same quality you’ve come to expect from every one of her songs. Much like Apple’s investments in hardware paid fruition when they essentially invalidated Intel’s existence with their own silicon, it’s not a question anymore — Taylor is the music industry. And that’s the difference between her and a Kanye — while he can’t keep his focus together and perpetually played footsie with potential album releases, she keeps putting music out.
This entire post could be about how mind-boggling it is that putting out #1 albums (that are actually good™) appears to be autopilot for her, but somehow, that’s a small percentage of what the idea of “Taylor Swift” is. So let’s rewind a bit.
The rep of finance people is all wrong. We don’t only care about money, we care so much about everything yes, because it could make us money, but also because a Master of the Universe is expected to understand as much about it as they possibly can. The most successful, brilliant people in finance that I’ve encountered are some of the most well-read, well-rounded people you’ll ever find. It’s the reason why notable hedge fund managers consider themselves philosophers (and painstakingly make us read their drivel) — we all want to be recognized as artists and titans of industry. The arrogance of thinking you can do both is a symptom of reaching the top. The next best thing to being an artist yourself is funding it, which is why the wings of major art museums read like a Wikipedia list of “most successful traders ever.” The perennial art dick-measuring contest between Ken Griffin and Steve Cohen is, in a way, authentic. It’s not a lack of knowledge that leads to these purchases, but the fact that the only way they know how to show knowledge is by appraisal and acquisition, hilariously satirized perfectly through the business card scene in American Psycho. The obsession with tastefulness goes all the way down to the margins on a Goldman pitch deck.
This is what sets the scene for my favorite Taylor tidbit:
Her father, Scott Kingsley Swift, is a former stockbroker for Merrill Lynch[3] and her mother, Andrea Gardner Swift (née Finlay), is a former homemaker who previously worked as a mutual fund marketing executive.
If you can’t do it yourself, you invest in it. In another timeline, Taylor would have been a poster on WallStreetOasis about the same fucking Jane Street interview questions again and again. I could have been Taylor is what the banker should think every time he puts on Delicate while working on a model at 1 AM instead of at that dive bar on the East Side he could have been at. The leverage she used would be on SPX options instead of the weight of her commercial force.
But that’s what makes Taylor the ultimate finance chick. Leverage, known as the most addictive drug in all of finance and the most destructive non-explosive force, is the most powerful social tool. It’s why we criminalize it when it goes too far (blackmail/extortion) or invalidate contracts when one side totally lacks any semblance of it. And Taylor is objectively the master of leverage, a better utilizer than anyone else in the history of music. Her list of iconic business moves looks like her nine straight number one albums. Take, for example, her decision to pull all her music from streaming services over a dispute about payment per play. In a move after my own heart, she published her op-ed in the Wall Street Journal, the only publication I’d ever want my writing in other than the New Yorker fiction section.
A friend of mine, who is an actress, told me that when the casting for her recent movie came down to two actresses, the casting director chose the actress with more Twitter followers. I see this becoming a trend in the music industry. For me, this dates back to 2005 when I walked into my first record-label meetings, explaining to them that I had been communicating directly with my fans on this new site called Myspace. In the future, artists will get record deals because they have fans—not the other way around.
This seemingly tepid observation that rings true when you understand the TikTok phenomenon understates how Taylor both min/maxed her own fanbase into a sort of recursive feedback loop — the mania about her shows drives the views and streams which drives the desire to go see her shows — and turned this logic on its own head by warping my view of how artists control their catalogue permanently by re-recording her old albums, presenting it as (Taylor’s version) in a hilariously petty, genius move to screw over the rights-holders to her old catalogue. I cannot fathom how much extra work went into that endeavor, which is currently ongoing. It also helps that, in many cases, Taylor’s version is better — the campy songs about romance written in her early years have an additional heft when sung by an artist in her 30s who has experienced (a lot of) relationship drama. The simplicity of the color similes in Red amusingly evoke pangs and nostalgia in the people that grew up with this music and are old enough to use it as a basis to contemplate while contextualizing an entire new generation’s emotions in her words. It takes money to make money, the saying goes — a slight alteration is that you cannot lose money with infinite leverage (as the Martingale proof would show), and Taylor is as close to infinite leverage as an artist will ever get, to the point where her ticket sales are so in-demand that the failure of the site selling them led to an antitrust investigation of a monopoly that has existed untouched for decades.
A constant question you hear in ordinary bars is why the ultra-rich continue to make money. Isn’t it enough at some point when you have more money than god? Beyond the vanity of running up the score, it’s almost what you live for at that point. Howard Schulz, through selling coffee, imposes his diktats on the world. Bob Iger built a corporation so powerful that it’s warring over policy with the 16th largest economy in the world, and appears to be winning. Anna Wintour isn’t going to stop curating the culture that leads to the guest list that enters the pearly gates on this side of reality. Steve Cohen returned to managing money and trading because when you have that much capital to allocate, you necessarily spend time learning and opining about everything. It’s what makes Jeff Bezos such an outlier; for all intents and purposes, he seems to have totally left Amazon behind. Never have I seen someone of that stature able to shake it off.
Taylor’s clearly not stopping anytime soon — her Eras tour continues until the end of 2024. Her concerts are practically a geopolitical force; her snub of Hong Kong in favor of six concerts in Singapore could legitimately be read as a wavering of the “investable” reputation of China and its proxies.
To be honest, I don’t fully understand the mania surrounding Taylor. The appeal of her music is plain to understand — it’s inoffensive and pushes up against the mathematical cap of how appealing a pop song’s construction can be — to the point where I can’t find anyone who genuinely dislikes her music for anything other than irrationally contrarian reasons. The most I’ll hear is “it’s not my cup of tea”. But much like Facebook has to reckon with how close they are to the singularity of “where do you go if everyone is on social media”, Taylor is perhaps as globally saturated as an artist can become through as much profitable decision-making as music she’s produced. It’s hard for me to see exactly how it took so hard, why “Swifties” became the most valuable TAM in music history, beyond Beliebers and the Beyhive. But hey, I’m not complaining — I’m gonna put on 1989 (Taylor’s Version) as soon as it releases, just like everyone else.