Caroline Calloway: The OG Social Media InstaScam

The podcast episode we've been wanting to do forever; the definitive guide to Caroline Calloway's rise to fame, subsequent fallout, and iconic place in pop culture as an OG social media scammer is here!
Guest-host Maggie Patterson, fellow podcaster and expert in online scams in business, joins the discussion. We cover so much ground, starting from the beginning; how Caroline's ivy-league fueled childhood led her to Cambridge, where her idyllic 'American abroad at a storied Ivy League Institution' aesthetic combined with long form narrative captions on Instagram gained her followers, fame, and a lucrative book deal.
Like many things we see on social media, all was not as it appears. After losing her book deal, she launches creativity workshops that promise social media branding tutorials, flower crowns, and artisanal salad. If you didn't know who she was yet, this is the point she pinged your cultural radar as journalist Kayleigh Donaldson outs her event as being a total scam in a Twitter thread and subsequent viral article.
We deep dive what the optics of her life looked like to her 800k followers, versus reality, as explored in The Cut's damaging article titled 'I Was Caroline Calloway,' written by former best friend (and as it turns out, writer of much of Caroline's words), Natalie Beach.
While Caroline's story could serve as a cautionary tale to influencers everywhere, we find ourselves wondering...is anyone on social media truly authentic? Whether they are aspirational influencers or relatable best-friend type influencers, they're all trying to sell you something. Caroline's story isn't unique, but leaning into her insta-scam persona and making the grift part of her narrative, is what makes her compelling. We debate whether she's the writer she claims to be, or a cunning performance artist.
Obsessions include Mindy Kaling's brilliant new show 'The Sex Lives of College Girls,' and Sex and the City reboot 'And Just Like That.' Will you ever look at a Peloton the same way?
So much to unpack in this show, buckle up!

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Helpful links we reference during the show / pop culture homework:

I was Caroline Calloway (Natalie Beach, The Cut)
The Case of Caroline Calloway and her Creativity Workshop Tour (Kayleigh Donaldson, Pajiba)
Caroline Calloway, her "one-woman Fyre Fest," and her ex-best friend Natalie, explained (Constance Grady, Vox)
"I Love Fame": How Caroline Calloway Survived Being Cancelled (Elle Hunt, The Guardian)
Caroline Calloway Isn't a Scammer (Caitlin Flanagan, The Atlantic)
Caroline Calloway Website

Listen to Maggie's Podcasts:
The BS-Free Serv