How Caroline Calloway went from Instagram influencer with a $500,000 book deal to the creator of her personal 'Fyre Festival'

Caroline Calloway/InstagramCaroline Calloway at the University of Cambridge.
  • Instagram influencer Caroline Calloway returned to the public eye this week after her ghostwriter and former friend, Natalie Beach, published a tell-all piece about her.
  • Earlier this year, Calloway made headlines after she cancelled and uncanceled her planned tour of “creativity” workshops after she was called out in a viral Twitter thread for backing away from her promises. (Insider went to one of these classes.)
  • Calloway has previously courted controversy – her publishers cancelled a reported $US500,000 memoir after she lost interest in writing it.
  • Here’s what we know about her.
  • Visit Insider’s homepage for more stories.

Caroline Calloway – an Instagram influencer with nearly 800,000 followers – was thrust back into the public eye this week after her ghostwriter and former friend, Natalie Beach, published a tell-all piece in The Cut about the Instagram star.

Earlier this year, Calloway cancelled and uncanceled her planned tour of “creativity workshops,” where for $US165 a ticket she’d teach aspiring influencers and creative types about how to find their voice.

Her plans blew up after Twitter thread chronicled how her promises shrunk from an expansive four-hour seminar where she’d bare her soul about the creative process and make a salad lunch for attendees, into a briefer lesson that included an hour-long meet-and-greet. She later announced a reboot of the tour via Instagram stories.

She has previously courted controversy: Calloway rose to fame in 2013, blogging about her life at the University of Cambridge on Instagram. Her posts turned into a reported $US500,000 book deal that her publisher ultimately cancelled after she said she lost interest in finishing it.

Here’s what we know about Caroline Calloway.

Calloway first got widespread attention for her Instagram blogs about the University of Cambridge.

Caroline Calloway/InstagramCalloway visiting Oxford University.

Calloway was born in Washington, DC, and attended elite schools private schools, including Phillips Exeter Academy for high school and New York University for her first two years of college.

She transferred to the University of Cambridge in 2013, where she began blogging on Instagram in earnest. Her idealised descriptions of the Cambridge campus and her confessional posts about her romantic life started gathering a substantial following. By spring 2015, she had 300,000 followers, according to The Daily Mail. People made fan accounts that tracked her every move.

At Cambridge, she told Broadly, she gained a reputation as “the Instagram girl,” saying people were dismissive about her blog.

“I would never say people are hostile, but people are a little condescending about [the blog] sometimes,” she told Broadly.

She also said her art history professors at Cambridge were snobbish about her work as an Instagram blogger.

“I could say with pretty much one hundred per cent certainty that no one’s thrilled that I’ll be the first one to be a professional Instagram blogger with my degree,” Calloway told Broadly. “Like whenever they talk about Caravaggio’s use of chiaroscuro or the use of contrapposto marble sculpture, I’m sure they would hate to know [they’re] being used to filter Instagram pictures.”

To her fans online, though, Calloway represented something rare – a life of both authenticity and aspiration.

“I enjoyed her prose and her openness in the beginning. It felt authentic that she so willing to share the good AND the bad in more than just an image,” one fan, Abigail Hope, told Insider. “I appreciated her vulnerability in her heartbreak and was drawn to her in some weird way I couldn’t exactly explain.”

Calloway graduated with her art history degree in 2016 – with a book deal in hand.

She signed a reported $US500,000 book deal in 2015.

Caroline CallowayThe book cover for ‘And We Were Like,’ which Calloway never finished.

By November 2015, Calloway’s reputation as a literary voice on the Internet helped her nab a deal with Flatiron Books for a memoir called “And We Were Like.” The total price tag for the deal was $US500,000, with her receiving a third of the funds in advance, she told Man Repeller.

The book was supposed to be similar to her Instagram posts: A memoir about her life at Cambridge and the relationships she had with different men.

Calloway was represented by Byrd Leavell, the high-profile agent who also represented Tiffany Haddish, Drew Magary, “S— My Dad Says” author Justin Halpern, and blogger Cat Marnell.

In her essay, Beach says that she helped ghostwrite the book proposal and was working with Calloway on the book.

Her publisher withdrew the deal after she lost interest in writing the book.

Caroline Calloway/InstagramCalloway said she wrote a 103-page book proposal in an Instagram post announcing her book deal in 2015.

Before long, Calloway decided she couldn’t finish the book.

“I promised a memoir where the only thing that happened to me were boyfriends and where the climax of my entire life experience to date was boy-related,” she told Man Repeller in 2018. “It wasn’t long before I realised the boy-obsessed version of myself I planned to depict as my memoir’s protagonist was not one I could stand behind.”

Her publishers withdrew her contract, she said, and asked her to repay her advance. But by then, Calloway had already spent her entire book advance: roughly $US165,000, according to her own figures. She said she spent it on rent for a London apartment, and on meals, and gave much of it away to friends.

Flatiron Books didn’t respond to Insider’s request for comment.

Since graduating, Calloway has continued posting about her personal life.

Caroline Calloway/InstagramEx-boyfriend Oscar and Calloway along with her dog, Winston.

Following college, Calloway moved to the posh West Village in New York City, and continued to post about her relationships, most notably, her three year relationship with a Swedish student named Oscar, which began in Cambridge and ended in mid-2016, hanging out with friends, and creative inspiration.

Calloway drew the ire of Oscar’s new girlfriend in the process, and the new girlfriend allegedly created an Instagram account to troll her. As Calloway recounts in her 2018 Man Repeller interview, she posted about the incident on her Instagram stories and it devolved “into this thing where people were saying she was crazy and evil and bad. I decided it was important for them to know that I have flaws, too, so I decided to tell them that at the very end of my relationship with Oscar, I kissed someone else.”

Another subject Calloway touched on was her use of Adderall. The blogger admitted that she’d used the drug for more than three years, both in and out of college, though she says she’s since stopped. In a March 2018 Facebook post she refers to having an “Adderall addiction.”

In 2018, she began posting about a new relationship with a man named Conrad.

She’s followed a more traditional influencer career path.

Caroline CallowayIn this Instagram story post, Calloway touted some of the 1,200 mason jars she purchased to make ‘care packages’ for her fans, and posted an advertisement for Away luggage.

Like many Instagram influencers, she’s made money mostly with sponsored content. In now-deleted Instagram posts, she said she began by charging brands up to $US1,000 for mentions in Instagram stories and $US5,000 for a regular post, and then more than doubled her rates after that.

In December, she expanded her ambition by planning a speaking tour.

Caroline Calloway/InstagramCaroline Calloway at her Washington, D.C. event.

Another source of revenue for many influencers is events. Calloway tried it out with “The Creativity Workshop,” a series of four-hour seminars where she promised to teach attendees about the creative process and finding a voice – along with a salad lunch she promised to make herself. Tickets were $US165 per person. She announced her plans for the series in December, and hosted the first event less than a month later, planning to hold similar workshops across the US and Europe.

The workshop series fell apart.

@libbwinn/InstagramOne of Calloway’s creativity workshops.

By January, the cracks in Calloway’s plans for a workshop series were beginning to show.

As journalist Kayleigh Donaldson described on Twitter, Calloway backpedaled her description for the event from a four-hour seminar with perks to a three-hour event with a meet-and-greet while asking attendees to bring their own food. People who attended the event said that while they had a good time meeting fellow fans, the experience was disorganized, and many things Calloway promised – including an orchid crown making workshop and “personalised” letters – never happened. The event series drew comparisons to Fyre Festival.

Calloway also failed to secure venues before announcing her tour dates and making tickets available for purchase. In one case, she promised to secure a venue and create an event in Atlanta on February 2, the same weekend as the Superbowl.

After holding one event in New York, she began cancelling dates in Boston, Philadelphia, and Denver, assuring that the people who purchased tickets for those events would receive refunds.

The whole thing was cancelled.

Caroline Calloway/InstagramCalloway at the University of Cambridge campus in 2015.

After Donaldson’s Twitter thread about Calloway went viral on Sunday, the influencer cancelled her additional tour dates, admitting that “greed” got the better of her.

“I was overconfident in believing that I had something to offer people that was worth $US165 dollars and this experience has been incredibly humbling,” she in a message posted to Twitter and Instagram. “I take full responsibility for letting my total inexperience with event planning and GREED create a situation where the details of the tour were ever-changing, preparation was inadequate, and the event did not match the description by the time it went on.”

Calloway said she would refund everyone who purchased tickets. But it wasn’t before she lost the faith of some of her fans, as Abigail Hope – a fan who’s followed Calloway for around four years – told Insider.

“It was a very surreal feeling seeing the original Twitter thread and realising all at once just how misled I’d been,” Hope said. “Misled, but also guilty of idolizing someone who I’d had no reason to glorify.”

Then, it was “uncanceled.”

Caroline Calloway/InstagramCaroline Calloway.

Soon after she had cancelled the original tour, Calloway soon “uncanceled” it, blaming her “haters” for convincing her to do so in the first place, she wrote in an Instagram story announcing the rebooted tour.

“I cancelled my tour because I was frightened and feeling worthless because if you read enough bad things about yourself on the internet you will start to believe they’re true,” she wrote. “You can’t let the people who despise you run your f—ing life.”

Calloway, who was accused of being a “scammer,” ultimately hosted a five-hour, $US165 “creativity workshop” in Brooklyn’s Bushwick neighbourhood.

Kathleen O’NeillCaroline Calloway, an Instagram influencer, hosting one of her ‘creative workshops’ in New York.

The Bushwick space was decorated with large, leafy plants, signature to Calloway’s brand. In a reference to the online comparisons the festival drew to 2017’s disaster Fyre Festival, Calloway hung a banner that read “Fyre Festival” in the space and dressed in a T-shirt that said “Scammer,”Business Insider’s Paige Leskin, who attended the event, reported.

Attendees were given custom journals and mingled with each other. Of course, the fans of the influencer also got to connect with the influencer who referenced the “journey” they had had been on “together,” Leskin reported.

“We’ve been through some crazy f—ing s— together,” Calloway said during the workshop. “You guys are in your own category of people I’ll never forget.”

The event concluded with each attendee taking turns posing photos with Calloway. Those who attended the event were also gifted a “care package” including things like a mason jar, notebook, candle, and a “crystal.”

In August, Calloway hosted another creativity workshop called “The Scam” which was much of the same.

carolinecalloway/IsntagramPromotional Images for ‘The Scam,’ which was held on August 3.

On August 3, Calloway hosted a sold-out “creativity workshop.” This time, the event was closed to journalists. Still, Vice’s Anna Iovine attended after purchasing a ticket under a different name.

The event was comparable to the January workshop. Attendees from near and far gathered in space in Kips Bay to share their creative work, engage in a community they are a part of online, rub elbows with Calloway, and collect their goody bag at the door.

When she’s not running workshops, Calloway remains active on Instagram, particularly stories. Lately, she’s been documenting her crafting on the platform.

carolinecalloway/InstagramCrafting has become a central part of her brand.

In the month between “The Scam” and The Cut’s revelatory essay from Natalie Beach, Calloway continued to be active on Instagram. The influencer continued posting photos with lengthy captions to her grid and real-time updates to her Instagram story of her day-to-day activities in New York City, like attending pilates classes.

Typically on the floor of her apartment, Calloway hand-paints “tittays” which sell for between $US80 and $100 USD, including shipping. More recently, she’s begun to sell hand-crafted “Matisse” cutouts, which retail for between $US180 and $US220, also including shipping. She creates and sells the crafts in real-time, also posting them to her Instagram story where her fans are eager to snap them up.

In September, Calloway’s ghostwriter, Natalie Beach, spoke out about her former friendship and partnership with the Instagram influencer.

Caroline CallowayThe book cover for ‘And We Were Like,’ which Calloway never finished.

Months after the speaking tour fiasco, Calloway’s ghostwriter, Natalie Beach, wrote an in-depth piece for The Cut, revealing how she used to help Calloway craft the stories that she became famous for.

Beach wrote that spent a summer editing Calloway’s Instagram captions and curating #Adventuregrams.

The tell-all essay added more controversy surrounding the influencer, describing, from Beach’s perspective, how the events surrounding Calloway’s memoir unfolded – noting that she helped ghostwrite the book proposal and wrote a quarter of the manuscript for the book that never materialised. Calloway previously told Man Repeller that her book deal with Flatiron clocked in at $US50,000. But Beach, who said Calloway agreed to give her 35%, said the deal was actually worth $US375,00.

Beach also alleged that some of Calloway’s Instagram following was purchased so that she could sell a memoir.

carolinecalloway/InstagramBeach and Calloway met as students at NYU.

Beach, who says she worked to develop the early voice and content for #adventuregrams, wrote that Calloway’s influencer origin story wasn’t exactly picture perfect.

“The real story, she told me, is she took a series of meetings with literary professionals who informed her that no one would buy a memoir from a girl with no claim to fame and no fan base,” Beach wrote. “And so Caroline made one online, taking out ads designed to look like posts to promote her account and buying tens of thousands of followers.”

This, Beach explained, happened before the Federal Trade Commission set rules influencers using the platform.

Today, Calloway boasts just under 800,000 followers on Instagram.

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