Unsurprisingly, it all blew up spectacularly in what many termed a one-woman Fyre Festival, which she documented painstakingly in her Instagram stories.
Recently, her ex-best friend and ghostwriter, Natalie Beach, exposed her grifting tactics in a scandalous tell-all published by The Cut. But who is Natalie Beach? Keep reading to find out.
Natalie Beach is a writer who claims she built Caroline Calloway's brand.
Born and bred in New Haven, Conn., Natalie attended NYU together with Caroline and developed a sort of sophomore-year infatuation with her classmate following a non-fiction workshop they were both enrolled in.
When Caroline discovered the fertile social media platform known as Instagram, which didn't yet have the following or Facebook ownership it does today, the two committed to building her brand and making Caroline a bonafide influencer.
"Instagram is memoir in real time," Natalie explains she believed at the time. "It's memoir without the act of remembering. It's collapsing the distance between writer and reader and critic, which is why it's true feminist storytelling."
Over the course of the following years, Natalie claims she wrote all of Caroline's Instagram captions, which contributed in great part to the nearly 800 thousand followers she has today. However, over time, she also started to see the gap between reality and what turned out to be a fictional narrative Caroline was constructing behind the scenes.
One of the biggest scoops of the article was when Natalie revealed that Caroline purchased her initial "tens of thousands of followers" in order to gain a book deal with Flatiron Books, the proposal and manuscript for which was entirely written by Natalie.
So, what happened to And We Were Like?
Natalie's article brings to light Caroline Calloway's book deal, one that was meant to be a memoir about the wealthy, revered, and endlessly vacationing socialite. "The Caroline character we created together was a fantastic YA protagonist," Natalie writes.
"She loved and was loved, looked good crying, stomped around an idealized New York in her 'I-deserve-to-be-here-boots,'" while Natalie — who claims she'd done a substantial portion of the writing with the looming promise of a portion of the $375,000 fee — played a supporting character in the storyline.
And though the book packs a punchy title, And We Were Like, which was chosen over Natalie's first choice, School Girl, it never got made. In fact, Caroline Calloway's website is still a splash page of the book's cover, and has presumably been so since around 2015, when the book deal first came about.
To read more of her stories, check out her website, here. And don't miss the opportunity to read her long-form tell-all on Instagram culture and grifting in 2019 on The Cut today.