Caroline Calloway Part 1: Essential Snake Oils

Missing Pages S01E04 

Caroline Calloway Pt. 1: Essential Snake Oils

Bethanne Patrick: The 2010s; a decade defined by the marriage between everyday people and the smartphones that would go on to rule our lives. Suddenly, everyone everywhere was online all the time.

Gone were the days of fuzzy flip phone photos. Now, anyone with an iPhone could point, click, and post. So began this unholy matrimony between teens, tech, and social media apps fueled by pictures.

Video Clip - Common Sense Media: This is Instagram. It's a social media app that lets users take, edit, and share photos and 15 second videos.

Bethanne Patrick: Upon its launch in 2010, Instagram’s aspirational slogan was: “Capture and share the world’s moments.”

Video Clip - Common Sense Media: It has a ton of cool filters, which makes posting images fun.

Bethanne Patrick: Oh, early Instagram. It was a wholesome place to be, where Millennials slapped a sepia-toned filter on their Starbucks order, called it “art,” and their followers would go wild. 

Instagram ushered in the emergence of on-demand photo diaries. And with the means of creation living at the bottom of your purse or riding along in your back pocket, suddenly, even the most mundane moments became content. Before celebrity publicists and social media managers flooded the platform, it was savvy twenty-somethings who understood the assignment.

Video Clip - HuffPost: I'm Caroline Calloway. I'm 23 years old and I live mainly in Cambridge, but sometimes in New York. As much as I think of myself as a writer, it just so happens that I've found an audience for myself in a place where every time I want to share a piece of my story with them, I have to do it visually as well.

Bethanne Patrick: Enter: Caroline Calloway. She used Instagram to document her experience at St. Edmund’s College, Cambridge in the United Kingdom. You can hear her talking to HuffPost in 2014 about her bedazzling social media presence. 

Video Clip - HuffPost: When I found out I got into Cambridge, I was like, this is amazing. This is everything I ever wanted.

Bethanne Patrick: And here’s where Instagram, Caroline, and the Book Publishing Industry tie the knot.

Video Clip - Ask Sunny: I grew up reading books like Harry Potter and Artemis Fowl, and I was like, you know what would be really cool is if I lived in a world like the world's in Harry Potter and Artemis Fowl. And I know that's sort of a silly dream to some people, to want to live in the world of your books, but I was like, this is the dream that's just really important to my heart.

Bethanne Patrick: Caroline, a history of art student, racked up half-a-million Instagram followers posting about her dreamy life as an American studying abroad.  

Video Clip - HuffPost: It is the most fairytale ice cream cone that has ever been eaten. Because you have the backdrop of these sort of Disneyland storybook castles.

Bethanne Patrick: On “the Gram,” the twenty-something married these charming, fantastical images of romance and academia in Europe, with long, prose-y, Live Journal-esque captions that documented the vulnerable stories behind each idyllic photograph. And as a lot of our stories this season go, Miss Calloway was doing something different and book publishing took notice. 

In 2015, she translated her Instagram following into what editor of Publishers Lunch, Erin Somers, might describe as a “significant deal,” or rather between $251,000 and $499,000. Oh, and If you’re interested in learning more about how book deals and advances are reported on, definitely check out our bonus episode where I interview Erin Somers. She’s an author and the editor of the Publishers Lunch daily newsletter, which reports on the latest deals.

In perhaps a sign of what was to come, Caroline told the press it was a flat half-a-million dollar deal. But like the honeymoon phase of every relationship, by 2017, the mood had shifted.  

Video Clip - TheThings Celebrity: Caroline Calloway is being called a one woman fire festival, which isn't the most flattering description. How did she go from scoring a half million dollar book deal to sitting in an apartment overflowing with mason jars?

Bethanne Patrick: Caroline Calloway's rise and fall has been well-documented by almost every corner of the internet. And her story is so big, we’re spreading it over 2 episodes. 

This is the only author we’ve covered on Missing Pages – to date – who, curiously, has never had an actual book published. We’ll get you up to speed on who Caroline Calloway is and how she fits into the story of modern book publishing.

Now, many have written about Miss Calloway’s tomfoolery… 

Video Clip - Celebrity Memoir Book Club: Okay, who the fuck is Caroline Calloway? I'm going to tell you everything you need to know about her in 60 seconds, and it’s a lot so here I go.

Bethanne Patrick: And yes, there will be some of that in this episode, but remember dear listener, this is a show about books, and in that regard, we plan to take Caroline seriously as an emerging author. 

Does the queen of clout even want to write? As many authors know, myself included, writing a book is a process. And especially for memoirists, excavating their life for the page, this process takes time.

Is Caroline part of a long tradition of messy and tragically interesting female memoirists? Or was the book deal, like her signature flower crown, just an accessory? Another shiny object to draw more followers into her attention-seeking vortex? Let’s find out together.

Welcome back to Missing Pages, the podcast where we reopen literary cold cases and find out if we all missed some important details the first time around. It’s me, your friend & host, Bethanne Patrick, Lit Critic, author, and dog mom.

There’s a lot going on in the Caroline Calloway story. So, in order to do it justice and include all the missing pages, we’re trying something a little different and making this story a two-parter.

Welcome to our first installment: Essential Snake Oils: Part 1 of The Caroline Calloway Story.

CHAPTER I:  A White Woman’s Instagram

Video Clip – Bo Burnham/White Woman’s Instagram: A Golden Retriever in a flower crown, is this heaven? Or is this just a white woman’s instagram?

Bethanne Patrick: Ah, who doesn’t love Bo Burnham’s Netflix musical comedy special “Inside?” And, come on, especially that song. What an instant classic? It’s all the tropes we love, combined with a compassionate, cool glass of water at the end here.

Video Clip – Bo Burnham/White Woman’s Instagram: Her favorite photo of her mom,

the caption says, “I can’t believe it. It’s been a decade since you’ve been gone.”

Bethanne Patrick: The song’s ending is a kind reminder that even the most filter-obsessed “it” girls of “the gram” are real people, worthy and deserving of our empathy. Appropriately titled “White Woman’s Instagram,” the tune captures just how the image-focused social media platform became a place where our fantasy of reality unfolds.

Speaking for myself, as, you guessed it, some white lady with an Instagram account, I can tell you firsthand: there is something gratifying about sending out a little filtered slice of life into the internet ether and receiving instant validation for merely existing. And wanting to share updates with your community, both as a private citizen or as an influencer, that’s totally normal. It’s above board behavior. 

But, I guess this is a story about when one Instagrammer took things a little too far. Where did the now infamous Caroline Gotschall Calloway come from? Let’s wrap our heads around her origin story.

Podcast Clip - Eyewitness Beauty: I'm from Falls Church, Virginia.

Bethanne Patrick: That’s Caroline on the Eyewitness Beauty podcast back in the fall of 2021, talking about her early life.

Podcast Clip - Eyewitness Beauty: I went first, [I] went to boarding school in Alexandria, Virginia, and then I went to boarding school in New Hampshire at Exeter. 

Bethanne Patrick: From boarding school, where Caroline describes herself as a bit of a fish out of water coming from a middle class background, our young ingénue applies to her dream school, Cambridge University in the United Kingdom.   

Podcast Clip - Eyewitness Beauty: So, I applied a second time. They reject me again. I start at NYU. I basically just throw myself into NYU, [like] Hermione Granger without the time turner. I start my Instagram, and then my sophomore year, I apply a third time and I get in.

Bethanne Patrick: Before heading across the pond to start at Saint Edmund’s College, Cambridge, Caroline sets up an Instagram account. 

Podcast Clip - Eyewitness Beauty: I don't know if you guys remember Tucker Max,
but the way that he got his book deal was really revolutionary. And I was like, you know what? I bet I could do what Tucker Max did. I could take that business model, apply it to Instagram, and get a book deal.

Bethanne Patrick: If you’ve never heard of Tucker Max, well, I envy you. Tucker is famous for chronicling, in snarky detail, his many sexual conquests. He’s known for his “fratire” or frat-boy satire. Cringe, I know. But he translated this internet identity into a lucrative book deal.

To jumpstart her Instagram account and gain traction, which Caroline sees as a path to getting a book deal, in the Eyewitness Beauty Podcast we shared earlier, she claims to have bought about 40,000 Instagram followers around this time, which we’ll get back to in a minute.

Constance Grady: So, Caroline Callaway, prior to this viral Twitter thread, was best known as kind of a minor Instagram influencer. She takes off around 2013 when she is an American student at school in Cambridge.

Bethanne Patrick: That’s Constance Grady. She’s a culture critic and journalist at Vox.

Constance Grady: Let me look at the exact date so I can get this all grounded down in time.

Bethanne Patrick: Constance is the brilliant genius who, in 2019, wrote one of the best and most comprehensive Caroline Calloway explainer articles on the internet. It’s referenced everywhere. She somehow made sense of the impossible.

Constance Grady: So, Caroline Callaway will tell you that she pioneered long Instagram captions. I do not know that that is necessarily completely accurate.

I would not say she's the only person in the world who ever thought of doing that in 2013. Certainly, she is one of the first people to have done it in quite such a large scale, and to have built her brand on it. 

I think what is attractive to her followers about that is that they're sort of vulnerable and confessional. It's kind of a throwback to sort of old school WordPress blogging circa, like, 2003.

Bethanne Patrick: As Constance explains, Caroline amasses a seemingly organic following and this leads to a very reputable literary agent giving the young, fresh voice a shot.

Constance Grady: Byrd Leavell is the most charming man in publishing, I swear to God. His thing is essentially signing very charismatic figures and pulling books out of them. So, he has worked with Tucker Max, he has worked with Donald Trump, he has worked with Cat Marnell. He has successfully gotten books out of all of these people. And that somehow does not seem to have worked out for him with Caroline Callaway. 

Bethanne Patrick: We reached out to Byrd for comment and, true to form, he was fabulously lovely via email but preferred not to revisit the Calloway years of his career. And when you hear what happens next, I think you’ll understand why.

Constance Grady: At the time, she has 500,000 followers, which is, I believe, what publishers were saying at the time was kind of like what you need in order to prove that you have a platform and you have people who are ready and excited to read your words and watch you work. And the book she sells him is sort of a continuation of the voice-y, escapist memoir that she started writing on Instagram.

Bethanne Patrick: This is where the Caroline Calloway Saga and my area of expertise, Book Publishing, collide. Between 2013 and 2015, she managed to translate her equal parts vulnerable and picture perfect online persona into what Caroline alleged was a half-a-million dollar book deal with Flatiron Books, an imprint of MacMillan. Other sources close to the deal have reason to believe it was under that half-a-million dollar mark, but moving on…

The book was officially announced in 2016. Aptly named, “And We Were Like” was the working title of her memoir, which promised to document her time abroad. 

Podcast Clip - Eyewitness Beauty: When I sold the big Cambridge book deal, I wanted to call it “And We Were Like” because I hate the way that like, people make fun of young girls for saying “like” in their speech. I don't like that at all. But, “and we were like” is a grammatically correct way to describe how a group of people were at a certain point in time. And I loved that, like, double meaning. The publishers made me change it to “School Girl.”

Bethanne Patrick: The title certainly had the feel of an instagram caption. You know, something with an aroma but you don’t get the flavor. Like a scented candle. Then, between 2015 and 2017, her Insta was overtaken with evidence of a working writer’s life. 

There were snapshots of books and pages strewn across the floor of her bohemian West Village apartment, where she moved after finishing undergrad abroad. On “the gram,” everything hinted at a book to come. 

Constance Grady: By 2017 she is saying that she is not going to be able to actually write this book and that she is going to have to pay back some of her advance.

Bethanne Patrick: Oh dear. By 2017, a slew of competing reports, and even contradictory statements from the author herself, made it seem like she was now on the hook to pay at least $100,000 of that book advance back to the publisher. Yikes! That’s what we call in the biz, not good. If publisher’s lunch categorized “outcomes” in the book industry, they might call this “not good.”

The next part of our influencer’s story, well that seems to entail a lot of attempts to “get rich quick.” In December 2018, Caroline announced her International “Creativity Workshops Tour” to followers.

Gabrielle Bluestone: Caroline Calloway is a one woman fyre festival, and I say that for a number of reasons, not the least of which is because she actually went viral at the same time that the fire festival did.

Bethanne Patrick: That’s journalist, lawyer, author, and producer Gabrielle Bluestone. You may know her documentary, Fyre, which detailed how a 2018 too-good-to-be-true music festival unraveled into an influencer travel nightmare.

We had to chat with Gabrielle for this episode because she literally wrote the book on our collective fascination with millennial con-artists, grifters and snake oil salesmen. It’s called Hype and there’s an entire chapter about Caroline Calloway. It’s a pageturner, but I digress. Back to the creativity workshops:

Gabrielle Bluestone: Her name started landing in my inbox, along with all the Fyre Festival reports, because she had been planning her own one-woman tour that was premised on the idea that she was going to be giving these literary workshops for her followers. 

Much like the Fyre festival, she was offering all these incredible perks. She had promised them that they would each get a journal with a personalized handwritten letter inside, and I believe she called it a portable DIY wildflower garden, which was influencer-speak for a mason jar with some flowers in it.

And then as she began selling tickets to it, another blogger, Kayleigh Donaldson, started to notice that something was terribly amiss. And so it's interesting when you look back, but what actually went viral wasn't Caroline's content, it was Kayleigh's thread.

Bethanne Patrick: As you can see, New York City media personalities became fascinated by Caroline on Twitter. Schadenfreude much?

As event dates inched closer, nothing was adding up. Here’s what Constance had to say about the event’s implosion:

Constance Grady: So, Caroline Callaway decided to host a seminar for her followers that was about, like, empowerment and being yourself. I think she was calling it a “world tour of creativity workshops.” And the idea was that she would charge $165 for the tickets, the seminars would be four hours long, she would only be there for three of the hours, and she was promising her attendees personalized journals, vegan lunches, and care packages that would include mason jar gardens. And the idea was they would drink coffee or tea, and there would be oat milk, and they would make flower crowns and wear them in their hair, and it would be in 10 U.S. cities and then eventually Europe.

So, she announces all of this on Instagram, but the thing is she does not have the infrastructure in place to actually do any of this. So she's selling tickets, but she doesn't have venues booked, she doesn't really even know exactly where each tour is going to be or what it will look like.

And the thing that becomes sort of the inescapable moment for this whole tour and an emblem of how the public is thinking about Caroline Callaway right now is she orders 1200 mason jars for those mason jar gardens. And she posts a picture to Instagram of this giant truck pulling up outside her apartment with a giant pallet full of 1200 mason jars. And she is realizing she has nowhere to store 1200 mason jars, [because] that's a lot of Mason jars 

Bethanne Patrick: As with her book, the reality failed to match up to the Instagram post about these events.

Constance Grady: Instead of making an orchard crown, which was what she promised in the event description, you get to put a single flower in your hair and take a picture and then return the flower. Like this is pretty knockoff. It's pretty shabby. It's not what she promised or sold anyone.

Bethanne Patrick: Meanwhile on Twitter, where you can find the keepers of the literati, like me – follow me @thebookmaven, wink wink – the people were cackling.

Constance Grady: So Caroline, in September, 2019, starts posting on Instagram about how her former best friend and I think she says, “The person who I've hurt most deeply in the world” is going to write an essay that will tell all.

Bethanne Patrick: New York Mag’s fashion, society, and more women-focused vertical, The Cut, published a scathing article about Caroline Calloway. 

Gabrielle Bluestone: The article was called “I am Caroline Callaway,” and it detailed how this young woman had basically created Caroline Callaway's persona for her.

Bethanne Patrick: Written by her former best friend and ghost writer, Natalie Beach, the article would go live in September 2019. 

Constance Grady: This is probably the finest thing she does is like, get everyone really excited to find out what Natalie Beach is going to say.

Bethanne Patrick: Ahead of its release, Caroline sent up smoke signals, demanding people pay attention to her on social media.

Video Cliop - Baited: In my creativity workshops, Google them, they were such a success. My book deal – I'm definitely not paying that back, [I] currently am in debt because of it. So, another resounding success. And the movie deal, I mean that definitely hasn't been postponed because of Corona [virus] and come to a total fucking grinding stand still.

Bethanne Patrick: On her Instagram story and during hastily booked internet talk show appearances, she admitted to being "awful,” and as an overdue “thank you” to Natalie, she wanted to ensure “every damn person” read Natalie’s article in The Cut. 

But at this point, Caroline was also capitalizing on the attention of the negative piece. She seemed to not only crave attention but to feed on it. This was the ugly side of what social media could do.

On Instagram, you can wield your white privilege and your youth to open lots of doors, but those same things can also be weaponized against you. Ultimately, the piece revealed a lot. Here’s Constance again.

Constance Grady: According to Natalie, she is the one who wrote most of the captions of Caroline's Cambridge adventure on Instagram, and also the followers that Caroline amassed on that time didn't come organically. She bought a lot of them. So, the followers that she used to score her book deal weren't necessarily real followers in the first place.

Bethanne Patrick: Those lengthy, authentic and vulnerable Instagram captions? That was Natalie’s work. The book proposal? Natalie’s writing again. And the over 500,000 Instagram followers? Beach claims that a good chunk of them were bought. And like in a lot of episodes of Missing Pages, nothing was what it seemed. 

This is where we needed Gabrielle to help us understand what the hell was going on.

Gabrielle Bluestone: You know, we tend to kind of, there’s an attraction to them, there’s a charisma there. There’s a confidence that people appreciate. And so, when I say con artists are the only criminals that tend to fail upwards, I mean that they're celebrated for what they do.

You know, they might get convicted of a crime, but people are going to buy their book afterwards. People are going to watch the TV adaptation and be invested in it. And in part, that's because the same qualities that make con artists so effective are the same qualities that we look for in leaders and CEOs and presidents.

Bethanne Patrick: How did social media, the illustrious life of one young, pretty, white woman, and book publishing collide? And like with a lot of things on the internet, was everyone enamored with Caroline Calloway, or was it just in this one neighborhood of loud, coincidentally, also white media personalities?

Deesha Philyaw: I’m not living under a rock, but her story, I missed it. I missed it somehow.

Bethanne Patrick: That’s my amazing author-friend, Deesha Philyaw. Keep listening. You’re going to hear more from her in the next chapter, right after this quick break.

Chapter 2: The Unfiltered Version

Gabrielle Bluestone: Caroline Calloway is someone who has existed on the internet, who has built an online persona that is so divorced from the reality of her life, that it really is almost, you know, like performance art. 

Bethanne Patrick: That’s our expert on millennial cons again, Gabrielle Bluestone.

Gabrielle Bluestone: So, she used her Instagram to parlay into a book deal that was supposed to focus on her as a young student at Cambridge. An American, you know, and in the Harry Potter world was kind of the way that it was posited. And she was able to use her following to essentially scam her way into a celebrity lit agent's office.

Bethanne Patrick: Now to be clear, Caroline has said she bought her initial base of followers, but she maintains the bulk of her growth came organically. Not to mention, paid growth opportunities aren’t inherently wrong, and oftentimes are a great option for people growing their brands. 

But like all things pertaining to Caroline, exact details are murky. Around 5-10 years ago, the publishing industry was really excited about social media. This was a whole new avenue for literary agents and book buyers to explore emerging audiences.

Gabrielle Bluestone: You know, social media, for example, really, I think has changed the way that we live and experience life. Unfortunately, you know, this idea of “FOMO” and doing it for the gram, people really, I think to a certain degree, have stopped experiencing experiences as they're happening and are now experiencing them more for how they can present them later.

Bethanne Patrick: And this is where two business entities, both notorious for exploitative behaviors, big tech and big publishing, cancel each other out. 

Gabrielle Bluestone: New York city influencer culture is a fascinating online world that is dominated primarily by thin, white, wealthy women who are able to process their lives visually in ways that are really enticing as a viewer. You see this and you want to live your life like that. You want your living room to look like “We Wore What's” living room.

And she makes sure that you know how she does it, tag all the designers with a helpful link that gives her commission on whatever you buy. So, there's, you know, the kind of style influencers, there are more, kind of, social influencers, people that don't have any clear job but are still somehow living very well.

You know, there are people who are influencers in, kind of, the literary world, whether they are writers or bloggers. But the thing that they all seem to have in common is having this wonderful, easy lifestyle that is digestible in individual photos and videos and monetizable.

Bethanne Patrick: Over the past few years though, something has changed on Instagram and really, across a lot of social media platforms. Aspirational is out.

Video Clip - Jack Gordon: Instagram is dying. Youtube, Twitter, and especially TikTok are taking over.

Video Clip - Ariane Sartor: So, a couple of days ago, I completely shut down my Instagram. I left cold turkey without warning anybody. I just posted a story and [was] like, “I’m not going to be on Instagram anymore.” 

Video Clip - heyDominik: Is Instagram dying or actually worse? Is it already dead? Truth be told, my friends, a lot of the old Instagram as we know it is, in fact, dead. It’s over.

Bethanne Patrick: Authenticity is in. But for platforms all about curation, is presenting your unfiltered self ever really possible?

Deesha Philyaw: So, I've been on Twitter since 2009. And you know, I look back at some of my old tweets and there's certainly things that I would not tweet today, you know? I think, you know, [I] definitely subscribe to a less is more philosophy now. Am I adding anything to the conversation?

Bethanne Patrick: That’s my friend Deesha Philyaw.

Deesha Philyaw: I don't typically talk shit about other writers on Twitter. I will talk shit about other writers in the group chat.

Bethanne Patrick: Deesha’s debut collection of short stories, The Secret Life of Church Ladies, won The PEN/Faulkner Award and The Story Prize, and she was a 2020 finalist for the National Book Award. And the rumors are true. The book is in production with HBO. The Tessa Thompson is executive producing. Deesha is what we in the biz call “a success.” This is yet another highly technical term.

Bethanne Patrick (in interview with Deesha): So, I'm going to read a couple of your recent tweets and then ask you – so for instance, this, I love. 13 hours ago. “I wish the dance battle in Girl’s Trip had been longer.” I love that.

Bethanne Patrick: As an influencer in the literary community, Deesha uses her platform to champion and celebrate other writers. You can also count on her to supply the unvarnished truth. But there’s an ethos to how she approaches sharing authentically.

Deesha Philyaw: The bumpers are: is there harm that can be done? Is there, you know, could a person acting in good faith misunderstand, and then there's kind of harm that's going to be done, am I adding anything to the conversation? You know, and that's maybe something I have regretted over the past, that sometimes I've said things that didn't necessarily add to the conversation.

And then now with the rise of the group chat, is this something that maybe I should just save for the group chat, you know? Is there such a thing as being too authentic, you know? Because it is sort of like privacy, like there's certain private things that, you know, none of us would share on social media.

And so, I'm sort of moving forward in this kind of, I'm very open with these little bumpers, these little safeguards to protect myself, to protect other people. But wanting to show up as who I am, where if you sit down and have dinner with me, I probably am the same, except I will swear more at dinner.

Bethanne Patrick: But Deesha didn’t wake up one morning with the National Book Award and HBO knocking down her door. This was a process.

Deesha Philyaw: In a way, I've been working on that book for over 20 years. I've been growing as a writer over 20 years to be able to pull that off, but the stories themselves, you know, they all, you know, probably originated around 2014, 2015.

Bethanne Patrick: The reality is most working writers have full-time jobs doing something completely different. 

Deesha Philyaw: I didn't allow space in my brain to even entertain the idea of being a writer when I was younger, because it wasn't practical. And it, you know, the whole idea of the starving artist, which is what I knew, it was either you were a starving artist or you were Toni Morrison. Right? And to be Toni Morrison is like to be Michael Jackson.

So, none of that seemed attainable to me, and [the] starving artist life did not appeal to me. I was a first generation college student, [from a] working class family, the idea was that I would go to college, get a good job, and be financially independent and stable. And I didn't know any art, first of all, I didn't know any artists, period, personally.

And I certainly didn't know any who were financially stable and independent, except the biggest names, you know, in the world. So, none of that felt feasible. I always got good grades in school in general, including on the papers that I wrote, but I was not given a lot of opportunities to write creatively when I was growing up, and neither in college, because in college I wasn't taking English classes. I was an econ major being practical.

Bethanne Patrick: And while Deesha’s story is uniquely her own, it’s more the norm than what Caroline Calloway was shilling on Instagram as a doe-eyed college graduate, who, almost by happy accident, stubbled into a book deal. 

Deesha Philyaw: When I got the offer, [it was an] absolute champagne popping moment. You know, so it was the only offer I got, the advance was teeny tiny, but I was thrilled. I had been trying to publish fiction at that point for 20 years, and it was happening, and I was over the moon. Absolutely over the moon.

Bethanne Patrick: The challenge for Caroline was two-fold. First, it was that she had sold a memoir on the idea that her social media presence closely resembled her authentic reality, which, as we later found out, wasn’t true.

Video Clip - Eve Donnelly: The reason people followed her wasn't so much her pictures as her captions. They were always really lengthy, almost blog-like paragraphs.

That was her claim to fame. She wrote some of the captions herself, but she had a lot of help from Natalie Beach, and that's kind of what she was exposing her for. Just ghostwriter things.

Bethanne Patrick: But there was this other, less obvious piece of the puzzle, which Deesha spoke to.

Deesha Philyaw: Someone that young is really at the mercy of their editor. And please, God, let them have a good editor because one of the things that, you know, doing this as long as I did, helped me to gain is a sense of my own strengths and my own weaknesses and the confidence and the maturity to engage an editor as a collaborator and not see them as like my mom.

Bethanne Patrick: Ah, a double-edged sword for Caroline. Her bubbly youth, something that made her an attractive social media personality,  well, that wasn’t necessarily an asset for her in the business of writing.

Deesha Philyaw: I've been around long enough to know more questions to ask. I still don't know all the questions to ask, which is why it's great to have an agent. But I knew more of the right questions to ask, and I just think that somebody super young, they're just so vulnerable, and they're really at the mercy of their agent and their editor. Do you even know yourself well enough? And just, maturity.

Bethanne Patrick: I can cut Caroline Calloway some slack for not spinning up a book within two years of graduating from college. That is possibly the most understandable part of the story. 

Deesha Philyaw: Absolutely. I mean, I didn't even know this at 32.

Bethanne Patrick: If you don’t know the nature of the beast, this big, bad, book publishing industry, like many tentacles of capitalism, has the capacity to eat you alive. Even writers with over twenty years of experience, like Deesha, can tell you that much. But does this excuse Caroline’s behavior? It reminded me of something Constance Grady said:

Constance Grady: I have a friend who always says that Caroline Calloway's whole deal is like Daenerys in Game of Thrones being like, “I am but a girl untutored in the ways of war.” You know, her whole deal is to sort of present herself as this sort of hapless naive innocent who's caught up in something bigger and more complex than she could possibly have imagined that always seems to somehow end in chaos.

Bethanne Patrick: In our next episode, “Heavy Is The Head That Wears The Flower Crown: Part II of The Caroline Calloway Story,” we fall even further down the rabbit hole. 

From the naivety of youth… 

Video clip - TikTok: There’s nothing that makes me want to do something more than being underestimated. 

Bethanne Patrick: to a foray into sex work.

Video Clip - TikTok: So, I needed a way to make money, and OnlyFans, I just felt like no one thought that I’d actually do it.

Bethanne Patrick: Plus, the ever-evolving pressures of social media/

Gabrielle Bluestone: Social media has changed from this presentation of perfection to almost like a manufactured authenticity, like performative authenticity.

Bethanne Patrick: When it comes to the illustrious life of our future memoirist, Miss Caroline Calloway, what else did we all miss the first time around? Stay with us. This next episode is a doozy.

If our first episode about Caroline Calloway piqued your interest in books about the messy, the vulnerable, and the influential or really millennial scammer culture in general, look no further than these juicy titles!

First, grab a copy of Hype by this podcast episode’s expert guest, Gabrielle Bluestone. It’s the influencer/scammer, non-fiction bible. With tons of scientific studies and expert analysis to back up the current cultural phenomenon of influencer con artists, it’s basically millennial grifter canon.

Despite (or perhaps because of) all its gross-out humor and Gen X-er depression, My Year of Rest and Relaxation by Ottessa Moshfegh is surprisingly popular with influencers. Read it in public. You’ll feel bad, but look good.

Caroline’s Instagram version of Cambridge owes more than a little to Brideshead Revisited by Evelyn Waugh, the great novel of British university nostalgia. Also, the perfect book for people who are Anglophiles, like our Caroline.

Finally, After Claude by Iris Owens is very funny when it’s not very sad. It’s a novel that begins with a bad date at The Film Forum and ends in dubious circumstances in the Chelsea Hotel; the perfect mix of seedy and cultured.

Missing Pages is a Podglomerate Original and is written and produced by a small army. 

Showrunner: Caila Litman

Producer, Researcher, and Writer: Jordan Aaron

Producer: Matt Keeley

Production, Mixing, and Mastering by Chris Boniello

Legal Review by Alexia Bedat and Louise Carron at Klaris Law.

Marketing by Joni Deutsch, Morgan Swift, and Madison Richards. 

Social Media by Sylvia Bueltel. 

Art by Tom Grillo

Legal Review by Alexia Bedat and Louise Carron at Klaris Law.

Fact Checking by Douglas Wiseman.

Production and Hosting by me, Bethanne Patrick. 

Executive Produced by Jeff Umbro and the Podglomerate. 

Special thanks to Dan Christo, The Eyewitness Beauty Podcast, Constance Grady, Brock Colyar, Deesha Philyaw, Zibby Owens, Gabrielle Bluestone, Lupita Aquino, Lena Dunham, and the especially chatty waitstaff at Minetta Tavern. 

We have included links to a lot of the background stories we used for this episode in the show notes. 

You can learn more about Missing Pages at thepodglomerate dot com, on twitter @misspagespod and on Instagram @missingpagespod, or you can email us at missing pages at the podglomerate dot com. 

If you liked what you heard today, please let your friends and family know and suggest an episode for them to listen to. I’m Bethanne Patrick, and we’ll be back next week with another episode.