Caroline Calloway was once the internet's biggest scammer. Here's what her life looks like now.

Caroline Calloway is arguably the world's most infamous influencer.

The now 31-year-old became known for her lengthy, intricate Instagram captions where she would catalogue her days while studying at Cambridge University, in London – which she had faked a grade to get into. Her captions would best be described as lengthy, poetic 'sad girl' verses.

But as her followers grew by the hundreds of thousands, her reputation became less tied to the fairytale lifestyle she would share online but synonymous with the word "scam".

It all started with her infamous book deal in 2016. 

Calloway had landed a deal – a goal of hers – with Flatiron Publishing for a novel titled And We Were Like. However, the following year, she withdrew the deal because she felt she had sold a facade to the publisher that didn't depict her authentic self. 

Calloway had already spent her book advance money when she pulled the plug. 

Watch the trailer for Inventing Anna. Post continues below. 

In 2019, she caused another stir when she offered her fans a "Creativity Workshop" tour, charging US$165 a ticket for a four-hour seminar. 

The first two seminars went ahead, with attendees reporting their disappointment at the lack of organisation. Calloway cancelled the remaining workshops and the "scam" went viral.

"I think that criticism is really valid and I apologise to anyone who felt cheated by the price point of $165," she wrote on her Instagram Stories at the time.

"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." 

Then, in 2019, her friend uploaded a cutting essay.

The former friend, Natalie Beach, wrote the piece for The Cut and alleged that many of those lengthy, poetic captions on Calloway's posts were written by Beach herself. Beach was also a creative writing student. 

Beach went on to detail their destructive friendship and Calloway's problematic method of achieving success in the influencer world. Beach reflected on her experience as Calloway's unknown paid ghostwriter, also claiming she soon became financially dependent on Calloway, who would behave erratically and once kicked her out of the accommodation she had promised her for the summer, essentially leaving her homeless.

"My involvement was uncredited, as the entire selling point of Caroline was that she was an ingénue," Beach wrote. "Caroline was caught between who she was and who she believed herself to be, which in the end may have been the most relatable thing about her."

Listen to Cancelled chat about the Caroline Calloway drama. Post continues after audio.

Ironically, this essay launched Calloway into mainstream media publications and, in her signature style, she leveraged off the infamy by announcing she was writing a book titled Scammer.

While writing the book, Calloway moved on to another product to sell. A $75 homemade skincare product she called 'Snake Oil'.

"We all know that I have amazing skin. Everyone knows this. This is just historically correct. I have the skin of a viral 18-year-old TikToker, and I am turning thirty," the influencer said in a video promoting the new product. 

Calloway explained to her followers that she has been mixing her own skincare oils for years. When her friends suggested she sold the oil to followers, she recalls telling them: "Oh my god, I love money. What a great idea."

She claimed the product is an "elixir of youth".

The influencer shared the ingredient list, which included grapeseed, neroli, carrot seed, clary sage, lavender, and ylang-ylang oil. 

In 2020 she said to The Guardian: "I love fame. I love being written about. I don't really mind if people think I'm a bad writer, if they don't understand my weird Instagram performance art or they find my long captions annoying. That's part of the package of being in the public eye, and honestly, I find it exhilarating."

As for the demise of her friendship with Beach, Calloway said she had sent Beach a "heartfelt apology" for being "a train wreck". Calloway said Beach accepted Calloway's apology but was firm about not rekindling the friendship.

Then for the next two years, Calloway retreated heavily from the spotlight. 

Only in April this year did Calloway 're-emerge'.

She posted a photo of her new book cover – Scammer, aka a book that was promised back in 2020 – and promised it would be live to the general public from mid-June. 

It's a title with negative connotations, but that doesn't matter to Calloway.

"I don't feel like I went after the moniker 'scammer'. I feel like I'm wisely playing the hand I was dealt," she said in a July 2023 60 Minutes interview.

"Everyone thought I was truly a white-collar, criminal mastermind who belonged in jail and I felt like that was unfair... I know I'm not like Elizabeth Holmes because they're in jail and I'm not. They did crime and I have never. So now I'm able to laugh at it."

In May, she appeared on the cover of Vanity Fair, doing a profile piece on what her life looks like today.

She also opened up on what she thinks it takes to 'survive' cancel culture.

"The rules that apply to surviving a riptide apply to surviving getting cancelled. Your first instinct is to struggle. You want to clear your name, and set the record straight. Don't. If you do, you'll expend your energy too quickly 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," she explained.

"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."

As for any reflections on Beach's article in The Cut and the demise of their friendship, Calloway was to the point.

"Natalie stole my identity with that piece…I alone wrote the captions that got me real followers, that got me fame. And then we wrote the book proposal together, half her words, half mine, because I was too high on Adderall to do it myself. Natalie was never my ghostwriter," she claimed. 

Much of the quotes Calloway gives in the article are quite inflammatory – almost said in a way to goad or rile up.

The journalist says the most apt description for Calloway is a con artist, with emphasis also on artist. And that she "isn't a writer but a performance artist's take on a writer".

In a final reflection in the article, Calloway stated what has now become a go-to line, repeated in her 60 Minutes interview: "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 were people can't retain enough information to remember every little scandal. Whereas if you have one scandal, people remember, and it defines you."

This article was originally published on May 31, 2023 and has been updated.

Feature Image: Getty.