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Back in 2019, The Cut published a story called I Was Caroline Calloway that went viral. I remember reading it and being completely fascinated, even though at that point I did not know who Caroline Calloway was. She’s an Instagram influencer who rose to prominence by documenting her experience transferring from NYU to Cambridge in the UK. It was all very fairy-tale ball-gowns-and-castles-and-boyfriends. Earlier in 2019 she was “canceled” for hosting a Fyre-Fest like creativity “tour” that turned out to be a giant scam. Then she was “canceled” again after I Was Caroline Calloway revealed that her Instagram captions had been ghost-written by one of her friends, Natalie Beach. Caroline then backed out of a $500K book deal with Flatiron in part because of an addiction to Adderall. What I’m trying to say is that Caroline was, and is, a scammer and there are a lot of things about her that are off-putting and surreal. And yet here she is, getting a glowing profile in Vanity Fair. It’s supposedly to promote her new book, aptly titled Scammer. But that book still has not arrived, despite Caroline’s promise that it would be published in mid-May. It’s now scheduled for June 16 but I’m not holding my breath.

The whole profile is equal parts entertaining and demented, and you can feel the writer of the piece, Lili Anolik, falling under Caroline’s spell as she writes. In person, there must be something charming about Caroline, as is often the case with scammers and narcissists. Caroline says some bonkers things in the interview about her ongoing lawsuit with her landlord, doing cocaine, and surviving cancel culture. She also says some things about the times we live in that are so perceptive it’s kind of surreal.

On her landlord suing her for $40K in back rent: It was an opportunity. I didn’t know when we’d see again the white-hot molten center of what’s cool in downtown New York embracing cancel culture in the ways that it did in the summer of 2021. It was a pop-culture lunar eclipse that I wanted to take advantage of. I’ve created a brand out of thin air. I’m a business. But banks don’t see me that way. Nothing but writing a book could ever make me a writer, but being there, with the right people in the right places having the right conversations, could make me in a much better position culturally for when my book did come out. And being there took money. I want to be an It girl. It girls are start-ups, and start-ups need funding.

On surviving being canceled: The rules that apply to surviving a riptide apply to surviving getting canceled. Your first instinct is to struggle. You want to clear your name, set the record straight. Don’t. If you do, you’ll expend your energy too quick and drown. What you do instead is follow the current, even if the last thing you want to do is go in the direction public opinion is carrying you. If you’re me, that means leaning into your scammer identity. You don’t point out that you offered everyone a refund. Or that the people the workshop was meant for actually had a good time. No, you name your next book Scammer. And then, once the undertow subsides, you can make your way back to shore.

She doesn’t take Adderall but does do cocaine: I don’t take uppers anymore. Well, I do a little bit of coke. A holiday amount of coke, you know? Like, I don’t do coke more days in the year than there are holidays.

How to take advantage of scandals: Listen, if you’ve never had any scandals, my advice would be to continue to have none. But if you’ve had one, have as many more as you can. It’s the Kardashian, Trumpian information overload fatigue. There’s a point where people can’t retain enough information to remember every little scandal. Whereas if you have one scandal, people remember, and it defines you.

[From Vanity Fair via Jezebel]

That last thing she says about scandals is true. That’s how 45 gamed the system. He knew that half the things he did would get memory-holed because our news cycle is so fast and people are so overwhelmed with information. What Caroline overlooks is that if your scandals are of the truly illegal kind, they may catch up to you. Just ask fellow scammer Elizabeth Holmes. For now, though, this strategy is paying off. She’s getting a feature in a major magazine and I don’t even know why–she must have a decent management team, I guess. Things are still being handed to her long after she’s proven that she won’t do anything with them… except somehow use each wasted opportunity to generate more controversy. Is she friends with Julia Fox? Because I could really see them vibing.

Also, her comments about cancel culture are interesting. That was the Taylor Swift playbook: embrace the villainy! Own your snake-ness! Caroline should lean into her scammer identity. It’s clearly what’s given her the social capital she now has. And it’s also who she probably truly is. There’s integrity in owning up to who you are. It doesn’t make you a good person, it just makes you honest. Caroline shouldn’t try to pretend to be someone she isn’t. She seems to be having fun with it: she truly, actually sells something called Snake Oil on her website. I’m not linking to it on principle, but it’s on there. But can scandal and scamming be the foundation of a successful brand? Can you really be a con artist if the sucker is in on the con? I’m not so sure.

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