After scamming her way into Cambridge, Calloway became known as the "Gatsby of Cambridge." But how much of it was real? Let's take a closer look at the influencer and how she earned the "one-woman Fyre Fest" title.
Who is Caroline Calloway?
There's something about us as a society that's addicted to watching a stranger live a life a "fairytale life," all while making us feel like we actually know this person. And that is Caroline Calloway.
Calloway might have first become Internet famous a decade ago, but with the arrival of her book Scammer, people are re-visiting the infamous influencer. All Calloway ever wanted was to be famous, and well, she did it. So, let's start from the very beginning.
Early Days
Born in Falls Church, Virginia, as Caroline Calloway Gotschall, the American influencer decided to switch her last name to Gotschall Calloway because it would one day "look better on books." She attended the Philips Exeter Academy growing up until she moved to Italy for a gap year.
In 2011, Calloway began her undergraduate degree in art history at New York University. However, her journey at NYU would eventually be cut short as she had rather different plans for her future. The young Caroline Calloway was looking for anything she could to earn a spot in the limelight.
Opening Instagram
After freshman year started, Calloway joined the app, Instagram. At the time, the social media app was just two years old, but Caroline sure did find her angle when it came down to using it. She would soon become one of the first of her kind, and by that, I mean the influencing kind.
Years later, she explained to Vanity Fair, "I got my Instagram handle in 2012. The app was up-and-coming. A typical post was an aerial shot of avocado toast and, for a caption, hashtag' Valencia.'" So, if there's any confusion about what the early days of Instagram might have looked like, Caroline cleared it right up for you.
Transferred to Cambridge
By 2013, she had dropped out of New York University and applied to study History of Art at University of Cambridge after being rejected from Yale, Harvard, and Oxford. And well, the third time was the charm for Calloway, as she finally got into Cambridge.
“I couldn’t live the rest of my life with an NYU email address,” she said to The Independent. However, years later, we find out that she forged her transcript when she got into the prestigious university. But, we would soon find out, whatever Caroline wanted, Caroline would get.
Instagram Fame
Her whole story started on Instagram once she got to Cambridge. She created an entire brand on Instagram alone, years before everyone else did it. "It was in January 2013, after Cambridge accepted me, after I dropped out of NYU, that I really started investing in Instagram," she told Vanity Fair.
She started using Instagram as a public platform for the intricacies of her daily life. With her openness and charm, she made people feel like they knew her personally, and inspired them to want to be like her. She was open, honest, and, above all, totally glamorous.
Living a Fairytale
By her second and third years in England, Calloway earned the reputation of being the "Gatsby of Cambridge." She began throwing parties at St. Edmund's College, getting people to obsess over her glamorous lifestyle. After all, she was an American girl attending the elite university millions of miles away from where she started.
She would post photos of her fairy tale life abroad, drinking champagne on top of the roof of a castle or studying art history in a chapel, and flirting with the endearing British lads. She told MailOnline, "I feel like I'm in Harry Potter, turning up for dinner in the grand hall in my robes and having beautiful three-course meals."
All in the Captions
By sharing picturesque photos of her luxurious lifestyle, Caroline created an Instagram fairytale that attracted many followers, even though it may not have been an entirely accurate depiction of life at Cambridge. However, what set Caroline apart was her blog post like, Instagram captions.
Caroline's long paragraph captions were informative enough that it almost read like a coming-of-age memoir. By disclosing such personal information about her daily life, like who she was with, what she was doing, or who she was dating, people looked at her as being vulnerable and, in response, trusted her and wanted to befriend her.
Scoring Instagram Fame
Her captions detailed her life as a "bright-eyed American undergraduate among a glamorous and decadent elite at Cambridge University," per Vanity Fair. And who doesn't love that combination? By 2015, Calloway had over 300,000 Instagram followers.
She was prepared to do whatever it took to make her life look as glamorous and desirable as possible, even if it was far from the truth. She told Vanity Fair, "I knew I wanted not just followers but readers, and not just any readers but readers who were predisposed to become obsessed with what they read." She had a plan (sort of).
Buying Her Followers
But how did she go from an Instagram nobody to an Instagram sensation overnight? Well, she bought her followers. A concept we are familiar with now, but at the time, it was unheard of. "I bought 40,000 followers for maybe $4.99," she told Vanity Fair. "I targeted book fandom accounts—Harry Potter, The Hunger Games—and bought ads."
"So, I spent all of my savings on this, plus more of my dad's money, which I would later learn he didn't even have. I'd buy a package of 10 posts for $50, which sounds insane," she added. "And that's how I started to get real followers." You gotta hand it to the girl; she's working.
Book Annoucement
Caroline's fanbase just continued to grow and grow as people became more and more intrigued by her and her American girl-turned-Gatsby of Oxford act. In 2015, the influencer announced she planned to release a book, School Girl, that would basically be an extension of her Instagram captions.
Literary agent Byrd Leavell represented her, and together they auctioned off Calloway's book proposal to the highest bidder, Flatiron Books. After the deal went through, Caroline told the press that her book sold for a whopping half a million dollars.
Where’s the Book?
However, Calloway never delivered the book she promised and the whole world. Byrd did everything in his power to get the book from her, but she started going completely rogue, and in return, she not only did not deliver the book, she hadn't even written it. Around the same time, she began posting about her addiction problems.
"I'm going to teach you how to get a book deal in the most self-harming, reckless way a twenty-three-year-old can," she captioned one of her posts. By 2017, she announced her original book proposal was not one she could stand behind. She now planned to write "a love story about a girl and her creativity," calling it And We Were Like.
Overdrawn
Caroline believed her original book plan was too focused on boys and instead wanted to show the world a different story. The publishers had given her a 100,000 dollar advance to write her first book, but the problem was she already spent every penny of it.
She now owed her publishers the 100K she had spent after not delivering any book to them; she put her book proposal up for sale on Etsy. Calloway began selling some merch on Etsy, spent time as a minor influencer, and offered to create sponsored content. However, none of it really panned out for her.
The Creativity Workshops
In deep debt to her publishers, Caroline was running out of ideas until she came up with this one. In December 2018, she announced she'd be leading a series of global "creativity workshops," and well, they went viral for all the wrong reasons. Calloway was charging $165 per head, but she conveniently forgot to plan the whole thing.
According to the event description, she promised a workshop for her fans to discuss all things creativity and how to build an Instagram brand with some arts and crafts. Attendees were told they would receive journals, vegan lunches, personalized care packages with mason jar gardens, and make a fresh orchid crown they could wear.
Viral Fail
Calloway began selling tickets just a month before her world tour was about to begin but had nothing planned out, including booking venues. Culture writer Kayleigh Donaldson started following her journey, calling her out for being "the worst" and criticizing her for charging her "$165 for a 4-hour 'seminar' on how to be yourself."
In a moment that would eventually become viral, Caroline ordered 1,200 mason jars, but when they arrived at her apartment on a giant pallet, she had absolutely nowhere to put them. Donaldson called her out for being a "blatant scammer," questioning why society "glorifies this 'influencer' nonsense."
The Workshops That Did Happen
After the mason jar situation had gone viral, the whole internet was encapsulated, calling her a "one-woman Fyre Fest." By the time the tour actually began in January of 2019, she announced all workshops would happen in NYC, canceling dates in other cities. And well, people were upset, to say the least.
For the workshops that did happen, guests sat on the floor and were given empty mason jars with a packet of wildflower seeds, calling it a garden. Instead of making the orchid crown they were promised, they were given a flower to put in their hair for a photo op that they would have to return. Some would call it a disaster.
Scarlet Scam
Those that bought tickets for her one-woman show in cities other than New York claimed they had major difficulties getting their money back from the influencer. Donaldson wrote, "To see the absolute disdain with which Calloway treats her fans for wanting the bare minimum she promised them was not a pleasant sight."
However, Caroline seemed to be unphased by her decisions. She told Refinery29 that she "leaned into my scarlet scam" era, citing Taylor Swift's Reputation era as her inspo. She even began a tour named "The Scam," where she created various merch for fans to buy, including a "Stop hate-following me, Kayleigh" tee.
Getting Canceled
She unknowingly reinvented her online identity from the Gatbsy girl to the scammer girl, but she was getting the attention she always wanted. Was she just a young college student who used social media and got way over her head, or was she really a scammer who cashed in her fan's trust for some cash? Regardless, the Internet was not happy.
The Cambridge alum was immediately canceled for her deceitful antics, but she stuck it through. She told Vanity Fair instead of struggling and attempting to clear your name, "set the record straight" when it comes down to getting canceled. "If you're me, that means leaning into your scammer identity," she said.
The Ugly Truth
Later that year, Caroline went viral yet again, but this time not by choice. Her ex-bff Natalie Beach wrote an expose for The Cut, named I Was Caroline Calloway, where she revealed Calloway as a "scammer," explaining their complicated and toxic friendship dynamic. In the tell-all, Beach discloses she was actually Calloway's ghostwriter.
Beach explained she edited all her Instagram captions, co-wrote the School Girl book proposal, and exposed Calloway for buying all her Instagram followers in order to attract publishers. Calloway would send Beach "raw notes," and in return, she would "credit it into a legible narrative," promising to give her 35 percent of the advance.
Caroline Calloway and Natalie Beach
Let's rewind for a second and take a closer look at the complicated relationship between Beach and Calloway. They were just 20 when they met at NYU, right before Calloway set off for Cambridge, but they hit it off right away. However, there was a very clear power dynamic between the two of them very early on.
Beach was mesmerized by Calloway's glamour and charm, and in return, Calloway was intrigued by Beach's praise for her and her ability to turn her into an idolized figure. A year into their friendship, Calloway opens Instagram with Beach's help, and together the two create an Internet sensation.
The Message Behind the Essay
Besides calling out Caroline for her lack of authenticity and dishonesty, the message behind Beach's essay was really focusing on what a friendship with Caroline Calloway was all about. Being best friends with a beautiful, wealthy, charming someone who appears to have everything you want but doesn't have to work for it.
While you, Natalie Beach, want what she conveniently has, putting in all the work to get there, but instead is just the ghostwriter. The essay gives outsiders the first real image of who Caroline Calloway really is as a friend, a writer, and a person, and well, it wasn't a good look.
Caroline's Thoughts
Following The Cut article, Calloway responded to her former friend, saying she was upset by her betrayal, but it was okay; she actually deserved it. "I've done everything in my limited power to set the volleyball of this essay at the net so Natalie can spike it down," Caroline wrote.
In fact, she uploaded multiple Instagram posts admitting Beach did teach her how to write and was the co-brain behind her infamous book proposal and Instagram captions. She called Beach an incredible writer and decided to do whatever she could to make her expose a big success. Confusing but brilliant.
Tragedy Strikes
"It was supposed to come out the day Jeffrey Epstein died," Beach said. "But fact-checking took so long that it got pushed back a month. You get lucky with how things hit and when." I Was Caroline Calloway became The Cut's most-read story of 2019; people were obsessed with her story.
However, just two days after the story was released and Caroline's name had gone viral for being a scammer and toxic friend, her father tragically passed away. Calloway's father died by suicide, and his body was found in her childhood home in Falls Church, Virginia.
Substance Abuse
Early on in her college years, Caroline developed an addiction to Adderall that would eventually take over her day-to-day life. According to Beach, it was her that introduced her to the substance in the first place. "If Caroline says I introduced her to Adderall, she's not making that up," Beach said.
"It's a guilt and anxiety that I carry knowing how much she's struggled with that drug," Beach shared. Unfortunately, this was a large part of Caroline's story, as she later shared she was "too high on Adderall" when writing her book proposal and that she needed Beach's help. "Half her words, half mine," she recalled.
Getting Canceled, Again
Following The Cut article and her father's death, the Internet was not feeling so sorry for the young influencer. Instead, they were canceling her again. However, she told Vanity Fair she gave herself a lot of credit for the "life-changing" attention she got, saying it "wasn't all bad."
"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," she advises. "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."
I am Caroline Calloway
Caroline took her own advice and continued to do whatever it took to keep her name relevant. So, in response to Beach's story, Caroline released her own personal essay six months later, titled I Am Caroline Calloway, on her website, where she attempts to explain herself in a different light.
The lengthy piece was written as a formal response to Natalie's The Cut piece and was delivered in multiple installments. In it, she shared more about her relationship with Beach and a series of emails between her and her former BFF. She also included information about her father and his sudden death.
Announcing Scammer
In the wake of all the controversy, Caroline took her own advice and continued to monetize off of everyone's fascination with her. In 2019, she announced she would self-publish the "Internet Trilogy," which would include Scammer, I Am Caroline Calloway, and The Cambridge Captions.
Scammer has been available for preorder since 2020. She said she would "cap it at a thousand copies" in order to "resell and get an advance from publishers so they could have the mainstream rights." She would finance her books by selling trinkets such as Snake Oil (her skin care product), Caro Cards (basically tarot cards), and more.
Reddit Culture
She had promised a book that was "AT LEAST 400 pages, more likely 450," and later announced it would be a "book of 65 prose poems than a 'memoir.' People were less than impressed with Calloway's antics, and soon a Reddit thread dedicated to trolling her was created.
People were dedicated to attacking her on the subthread, calling her a "narcissistic sociopath," so she decided to take matters into her own hands and begin calling some of those obsessive fans. She wanted to understand how they could say such horrible things without knowing her, with the goal of understanding how they are human too.
Love for the Limelight
With all the hate from Reddit coming her way, it's fascinating to think that Calloway was once so obsessed with being the center of attention, regardless of the positive or negative effect. "I take up a lot of space online, and I'm not that famous. And that's what I'm most proud of."
She continued to tell Varsity, "I want to be famous. I want to be rich. I want to live comfortably." Caroline also explained the benefit of "fakeness," explaining that pulling "in the likes and what actually keeps a community quiet and calm is just faking it to a certain degree."
A Financial Pickle
But with all her love for the limelight, Calloway continuously hit major financial roadblocks. "I've created a brand out of thin air. I'm a business. But banks don't see me that way," she told Vanity Fair. "I want to be an It girl. It girls are start-ups, and start-ups need funding." But Caroline took her funding and burned it to the ground.
She ended up leaving NYC with a giant lawsuit on her back after owing her landlord $40,000, and moving to Florida. She had no money to her name and was doing anything she could to attract attention, including joining OnlyFans. She decided the best move of all was to leave NYC, but she left behind a giant mess - literally.
Scammer
Caroline explained that she didn't see any way forward other than to "embrace" her story. So, after years of excuses explaining why Scammer hadn't arrived yet, Caroline confirmed on her Instagram that, as of June 2023, "the first few copies of Scammer have shipped."
The author decided to pick up and move to Florida, where she lives in her grandmother's apartment with her cat, Matisse. After wiping her Instagram a few years ago, her profile now mostly consists of her promoting her book, as she says she spends all of her days just reading and writing. Well, it's our time to get a copy of Scammer!