Who is Florida Instagram influencer Caroline Calloway? And why is she known as a scammer?

Melissa Pérez-Carrillo, Sarasota Herald-Tribune

June 16, 2023 at 2:56 PM·3 min read

You’ve heard about scammers Anna Levey, a supposed German heiress, and Elizabeth Holmes, a fraudulent startup owner, but have you heard of Florida’s own Caroline Calloway?

Pining to those who religiously follow lifestyle influencers, Calloway started her first Instagram account at 20-years-old by purchasing 40,000 bot followers. She hired her then-best friend to write her captions, and the rest was history – or herstory.

After gaining traction with her Instagram account, Calloway developed a persona as a "scammer" when she failed to deliver several promises, including a national "creative workshop" tour in 2019 and a failed book release in 2020 that escalated her rise to fame.

Caroline Calloway has trouble explaining her online presence to the 98-year-old Harriet Burns Stieff, the youngest daughter of Sarasota real estate mogul Owen Burns.

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Is her book finally published? Did she really lie on her Cambridge application? Here's a breakdown of the decade-long saga of one of Sarasota's most Internet-famous residents, and in the words of Calloway, "The girls who Caroline Calloway will get what I'm about to say, and the girls who don’t Caroline – Callo-won’t."

What is Caroline Calloway famous for?

The Virginia native was catapulted into Instagram fame in the early 2010s with her diary-like captions that described her lush life at Cambridge University. From Valentine’s Day in Paris with her on-again-off-again Swedish polo player boyfriend to the balls, gowns and parties at one of the world's oldest universities, Calloway laid it all to bare. It made followers feel like they knew her and were friends with her in real life, strengthening her following.

For the next decade, her name would intermittently pop up in national headlines for being a "scammer" after her failed book deal and admitting to lying on her University of Cambridge applications. It's an identity Calloway leaned into as a branding tool.

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Her great-grandfather was a Sarasota real estate mogul

Owen Burns, first Commodore of the Sarasota Yacht and Automobile Club.

While she grew up in Falls Church, Virginia, Calloway has been living in her grandmother’s condo in Sarasota. She is the great-granddaughter of Sarasota real estate mogul Owen Burns. He had a key role in the construction of several historical buildings in Sarasota, including Burns Court, Herald Square and the John Ringling Hotel.

"He came to Sarasota in 1910 and was a leader in practically every movement that saw Sarasota grow from a fishing village to one of Florida's leading resort cities," said the Herald-Tribune's obituary of Burns in 1937.

How did she get into Cambridge?

After being rejected twice, she finally got into Cambridge by lying on her application, Calloway told Vanity Fair in an interview.

What were all the “scams” she did?

These were the "scams" that Calloway admitted to and discussed in interviews and on Instagram.

The book. She received a $500,000 book deal in 2016 from Flat Iron Publishing that included a $150,000 advance, but she backed out of the deal after struggling with mental health and addiction. Pre-orders for the book were sold in 2020, but the book wasn't delivered as it wasn't completed.
Creative workshop tour. In early 2019, Calloway went viral for failing to deliver a hefty national tour of “creative workshops.” She forgot to book venues and ended up just refunding people.
University of Cambridge. She was accepted into the school in January 2013, but Calloway told Vanity Fair that she lied on her application and forged her transcript when she got in.

Is she finally getting her book published?

View this post on Instagram

A post shared by Caroline Calloway (@carolinecalloway)

After years of promises and pre-orders her self-published book "Scammer" is finally being released. A limited batch of 600 pre-orders are available for $65 on her site. She has limited the copies of the book with the hopes that it'll be picked up by a larger publishing company.

Calloway said in an Instagram post that fans who pre-ordered (but never received) the book in 2020 will be receiving their copies first.

This article originally appeared on Sarasota Herald-Tribune: Who is Florida 'scammer' Caroline Calloway? Here's what to know

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