Caroline Calloway

Calloway joined Instagram in 2012 with the help of her NYU classmate Natalie Beach.[1] The Instagram account documented her life at Cambridge and contained long captions.[8] Calloway bought followers and purchased ads to grow her account.[9] She became known as the "Gatsby of Cambridge" for the lavish parties that she documented online, which she hosted in rented rooms at other Cambridge colleges that she considered more Instagram-worthy than St. Edmund's.[6]

In September 2019, Beach wrote an essay for The Cut, "I Was Caroline Calloway", chronicling her friendship with Calloway and disclosing that she had ghostwritten a number of the Instagram captions credited to Calloway and collaborated with her to produce a subsequent book proposal.[2][9][10]

In July 2021, Calloway began selling a homemade blend of grapeseed oil and essential oils branded as Snake Oil through her website.[11][12][13]

In 2016 it was announced that Calloway would publish a memoir titled And We Were Like about her time at Cambridge with Flatiron Books, an imprint of Macmillan Publishers, with the help of literary agent Byrd Leavell.[14][1] During her final year at Cambridge, Calloway had hired Beach to co-write the book and proposal.[15] She then set up an initial meeting with Leavell by pretending to his secretary that she was already his client.[1] Leavell has since said of his experience working with Calloway that she was "deeply unwell, deeply dishonest" and that "It was more important to her to be seen as an author than it was to be an author."[16]

Calloway publicly announced that Flatiron Books had offered her a book deal to write a memoir for US$500,000 in 2015, of which she had received 30% as an advance.[17] She announced via her Instagram stories in 2017 that she was withdrawing from her book deal after failing to fulfill her contract.[18] Beach reported the deal was for US$375,000, and the advance she received was actually for US$100,000, which she owed back to the publisher after she canceled the deal.[1][10] After that, Calloway offered the book proposal with personal annotations for sale on Etsy.[18]

In December 2018, Calloway launched an international "Creativity Workshop Tour". Her original announcement indicated that the workshop would offer tutorials on building an Instagram brand, developing ideas, and addressing "the emotional and spiritual dimensions of making art."[19] Participation in the tour was priced at US$165 per person, and tickets were sold for events in Boston, Denver, San Francisco, Los Angeles, Atlanta, Chicago, Dallas, Austin, Charlotte, and Washington DC.[18] This tour was subsequently canceled due to Calloway failing to book venues for these events, with Calloway announcing that she would refund those who had already bought tickets.[9][18] Eventually, Calloway held two workshops in New York.[20] The cancellation of the workshops gained public attention when reporter Kayleigh Donaldson created a Twitter thread that gained news coverage comparing Calloway's tour to Fyre Festival, later publishing this as an article for the online publication Pajiba.[19][18][21] After the publication of Donaldson's article, Calloway briefly offered t-shirts for sale on Threadless that bore the caption "Stop hate-following me, Kayleigh".[22] Threadless suspended sale of these shirts for violating its targeted harassment policy.[22]

In August 2019, Calloway held a second creativity workshop, "The Scam", in New York.[23] Although press was not invited to the event, a Vice reporter bought a ticket, attended the event under a false name, and published an article about her experience.[23]

In 2020, Calloway created an OnlyFans account, promising videographic and photographic content containing nudity.[24] She alleged in interviews that her intention to enter the adult entertainment industry had been planned by Playboy, and that the magazine had commissioned a photo shoot of her dressed as a student in a library.[25] When asked, the magazine stated: "Playboy does not have and did not have any photo shoot planned with Caroline Calloway."[25] Calloway has described her sex work as "emotionally poignant, softcore cerebral porn."[26] Her content includes cosplay of characters from children's movies such as Harry Potter, Matilda and Beauty and the Beast,[27] and partially undressed photographs of herself captioned with details of her father's autopsy.[28][25]

Calloway posted her projected income from sex work on her Twitter account in May 2020, leading to criticism about her failure to recognize difficulties faced by sex workers, as well as her attempts to distance herself from sex work.[29][27]