Ep.51 Victim or Scammer: Who Really Is Caroline Calloway? ft. Caroline Calloway

0:00I'm incredibly excited to talk to you. Caroline first made her name by lying her way into Cambridge University. You're a scammer. I overpromised and I underdelivered. If you've had one scandal, have as many more as you can. Otherwise, that one scandal will define you. You've stolen money from people. So deeply unlikable. This shit's fucked up. Just stop from the beginning. I lied on my application to Cambridge and I got in. It really only went downhill from there. I was a terrible person during my addiction. Even one month without my prescription would be unthinkable. I meet a girl and I hire her to write captions.

0:39Natalie reaches out to the cut and pitches her tell-all. In her story, she crafts this really, really conniving narrative. And I saw that she had actually taken credit for my work. And then two days later, my father's body was found. But I still owe the$100 ,000. I'm trying to think of ways to pay it back. Having heard all of these stories from you, I don't think you genuinely believe you're a scammer. There's so much to talk about. I want to get into it.

1:16So today is a day that my Oxford self never thought would happen. I started following Caroline Calloway when I was at university and I had heard about her various kind of ups and downs and the perception I had of her career was that she was one of the first people on Instagram she was one of the first people to truly blow up on Instagram from her work so from her you know from her writing from her telling the story of her at Cambridge and there started to be I guess more and more controversies around her so there were a few things that you You know, she got a$500 ,000 book deal. The book never kind of came to life.

1:55There were these workshops that went wrong. There was a tell-all article that suddenly catapulted her to viral, viral fame. Every single outlet was covering this story. I mean, I was always so intrigued by all of this. It's almost that type of intrigue that you get from a fire festival type thing. but what it always intrigued me so much about Caroline was that you see her stuff and you see her writing and you see her career and of course she's done you know there are things that have definitely gone wrong and there are things that you know she definitely should have been held to account for but the magnitude to which there was a response around this kind of scammer persona that she came to be felt so disproportionate to what she actually had done at any one time it was like it acted like it was a kind of fire festival type thing and what I've always wanted to do and always had a wanted to have a conversation about is like how true is this scammer persona I really wanted with this episode to kind of have a deep dive into Caroline's life her story for people who might not know about it for people who probably haven't read the book yet I've got a press copy so that's how I've read the book and I wanted to dive into it and find out how much she really thinks that she's even a scammer and how much she you know has instead just played up to this because she's always wanted to be a famous memoirist and she's always wanted to write you know she talks in the book about how she always knew that she was going to be famous she just didn't know what for and the fact that Instagram didn't wasn't kind of invented at that point I think it's so interesting because I think it's such a story of our time like it's such a Instagram story in the way that Caroline's purpose was always to become a memoirist and so she had to act like a memoirist at this point now she's written a book but for the past 10 years she's been known as a writer or a kind of not writer before that things even existed if that makes sense and what I really want to do with this episode is to hear it from her and hear the story from her hear the tell-all Natalie kind of situation from her where you know her best friend essentially came out and claimed that she had written everything and that she was Caroline Calloway and then in the end you know tried to get Caroline to sell her her life rights for$15 ,000 at the point that Caroline was in deep depression because her father had just been found dead from suicide.

4:16It's just the most unbelievable story and I really wanted to dive into this story and find out what is the truth, what is the scam, what is played into as a persona, like how much is this as a persona, does this have an end date, is it only a persona because it is the thing that got the most press. I really wanted to make this episode happen. We don't do any remote episodes. This was a complete exception to that rule and I hope you really enjoy it. I really wanted to dive into it. I particularly thought it would be interesting going from the place of actually on paper we are really similar. We both started on social media and kind of blew up while we were at Oxbridge and were sharing that experience and that was really what kind of captivated people's attention online and our lives have been so different in so many ways and we are so different in so many ways, despite all of these parallels.

5:01I really wanted to kind of explore that. So I hope you really enjoyed this episode. It's slightly different from our usual episodes. And I really wanted to give Caroline the space to just tell it all. So this is really storytelling from her side. I do have to say I've read the book and she is a fucking phenomenal writer. I texted every single person who knows who Caroline Calloway is while reading the book and after having read the book, just saying, if she wanted to be a memoirist, that is all she ever had to do, just get down and write. because her prose for anyone who likes beautiful writing I wouldn't care what I was reading about I could read about her going to the shops and it is the you know it is she is a truly incredible artist and writer and I do think that you can tell through this episode how she more than anyone I think she very much does embody that troubled artist who's been through a lot and but her ultimate aim will always be the art um and I think we don't see a lot of that so it's been incredibly interesting to hear it from her I definitely advise and recommend getting the book no matter what your kind of thoughts are on the whole situation I think it's a fantastic book and I think that has it value in its own right and I hope you really enjoy this episode so as always thank you for listening if you do enjoy this please make sure to rate and subscribe or follow or I don't really know what platform you're on but it helps us get good guests and it helps my ego so I hope you enjoy and as always have a lovely day

6:27Known for her hugely captivating story, writer, social media influencer and self-titled scammer, Caroline Calloway doesn't shy away from being controversial. Caroline started to build her online presence between 2013 and 2016, documenting her experience during her time at Cambridge University. She rose to fame creating an Instagram following who were given exclusive access into the life of Caroline Calloway and her adventures. However, while she gained significant traction and a dedicated fan base which gave her followers a real insight into her life, she began to face criticism for her sometimes inconsistent accounts and stories.

6:59It was later revealed that alongside forging her place at Cambridge with fraudulent results, she had bought Instagram followers before building an actual audience online. In 2019, Caroline promised a memoir, And We Were Like, as part of a$500 ,000 book deal off the back of her internet popularity, but the book never transpired, landing her in$100 ,000 of debt to the publisher. It was later alleged in a damning article published in 2019 by her university friend Natalie Beach that she was the brains behind the famous Instagram, revealing the apparent truth behind the book deal. Just two days after the article was published, Caroline was told that her father had been found dead from suicide.

7:35Fast forward to present life, Caroline has now, finally, published her memoir Scammer, giving a tell-all take into her life and answers some of the questions that left from her controversies. Since her controversies, Caroline has positioned herself as a scammer, but how true really is this? this episode gets behind the Instagram profile looking at who actually is Caroline Calloway from following a similar path and attending an Oxford University and building a following at the same time to where our paths kind of divided and how they've been so different this episode cross-examines her one-of-a-kind story as I try to work out the real truth and whether if she really is a scam artist at all so I want to start at the very beginning set the scene a little bit for them A little bit of background, your elevator pitch, Caroline, up to the point of you going to Cambridge.

8:20I was born in a hoarder home. It was a very not-cassily beginning. And I had a very mentally ill, unstable father who was also a genius but had rage problems and was agoraphobic and probably on the spectrum. and I sort of retreated into the stories I could tell myself as an only lonely child. And on top of that, I think there was just madness in the blood. Like my father would end up killing himself. His brother had to drop out of Yale because he was schizophrenic. And ever since I was little, felt really compelled to grow up and be a very specific kind of writer. I wanted to be a memoirist, but I didn't want to write about any old events.

9:15I wanted to write about the things that happened to me at elite institutions, and I pursued it above all else. I got rejected from a really good boarding school, sort of like the Eton of America, except they accept women, and got rejected, applied again, got in, graduated from there, applied to Cambridge, got rejected, applied to Cambridge again, got rejected again. And I applied to St. Edmunds and get this, I also lied on my application to get in. And then I finally got into Cambridge. And I lied about three of the grades that I wrote on my application and I got in. Why did you want to go to Cambridge so badly?

9:59Like obviously you transferred from NYU, so you had already done a few years of college as well. Why was it something that for you meant that much? Was it an escapism thing? Was it a academic achievement thing? You know, I don't think there's any one simple answer to it. And you know, it's funny you say that I transferred from NYU, but fun fact about Oxford and Cambridge, they are so full of themselves that they do not accept transfer credits from anywhere in the world except each other. I could have been coming from Harvard and they still would have said the year and a half of college that you've already done does not count.

10:37But I did do a year and a half, my freshman year and half of my sophomore year at NYU. And coming to Cambridge, it was definitely an academic achievement thing. I don't know if you ever felt growing up being young and blonde and conventionally attractive, if you just sort of felt like people gave you the Elle Woods treatment, They just severely underestimated your intellect. You know, especially having an American accent, especially in a female body, just don't usually pair that with intelligence. As soon as I got there, like, although I did think that things might get better, at a certain point I should have realized that they only got worse in terms of, like, the bullying was really bad.

11:23You know, I arrive in 2013 to Cambridge. Instagram had only been invented, what, two years prior to that? I was really unhappy there. People didn't take me seriously. And my unwillingness to change just made me stick out more. Once I got there, though, and saw it with my own eyes, the beauty was intoxicating. And I did enjoy the eyeball pleasure of it all. But I stayed there and stuck it through and, like, mainly pursued it in the first place. I always had this really deranged goal that I just fundamentally, more than academic achievement, more than wanting to like escape into the storybooks. I've just always been possessed by this overwhelming belief that my greatest contributions to society, it won't be as a mother, it won't be as a politician.

12:15I've always, always, always thought it would be writing books about a very specific world. And it's so interesting because it's, it feels like to me, the concept of being a memoirist and the story that the memoir could tell takes far more importance than your actual enjoyment of something. I don't know if that's fair to say. No, totally. Do you think it's been enjoyable for me to watch the British press like go crazy with the headline like this girl lied on her application to Cambridge and admits it in her first book? Like I've been online for 10 years. For the first five I was a fairy tale. For the last five I was a scammer.

12:55And like I get the press. I even get the British press, even though it's like not my native country. I think I understand the British media pretty well and how the media really likes to weaponize poshness against those who either wield it or value it in order to mobilize the masses of England with anger in order to like drive traffic, to sell copies, get clicks. Like I very much understand that dynamic and understood what I was setting myself up for. But I just think it makes a better book to be honest about it. I just think it makes more compelling, jaw dropping art. It's so interesting because there's your persona and your kind of outward perception as a scammer.

13:42A lot of what's made you perceive to be the scammer is actually your honesty around the things that you've done wrong. And I think we have like this very strange perception of truth and untruth and right and wrong on social media I think a lot of the time things are only as bad as you make them and you have made it your mission to like play into the scammer role and to make it like even worse and so it has become even worse and so you know it's so interesting and I want to go into this later on the things that you have been quote-unquote cancelled for are nowhere near as big as some of the ones that some other people have been cancelled for and yet purely the fact that you've played into it and exacerbated it and made it your brand it's given the internet permission to never move on from it and I find it really interesting hearing you talk about that sure that was the decision that made probably the best book and got the most press do you feel like it was the right decision for you as a person retrospectively looking back on it I think like something about growing up with intense depression and I owe so much to being on the correct medication.

14:49I think it could have saved my dad's life. But the thing about any sort of mental health treatment, even addiction treatment, like you have to want to change. Like you can't ever want it badly enough for someone else that they seek it out themselves. Like you have to actually want it. When you went to Cambridge, how soon after that point did you start your social media? This is where the timeline always gets a little gray for people. So I'm going to try to be as clear about this as possible. I started my Instagram account when I was at NYU, still being rejected from Cambridge, hadn't gotten in yet.

15:23And at NYU, I buy 40 ,000 fake followers. And this is very important to understand for two reasons. One, the year was like 2012. Like 40 ,000 fake followers truly cost me like$4.99. And I always feel like an old person being like, soda pop used to cost a nickel like when I tell people that but truly like in 2012 buying Instagram followers was like throwing your money away like the concept of influencers and influencer marketing and hashtag ads and like digital promotions did not exist yet so I bought these followers basically to just like cosplay fame I just thought like oh wouldn't it be so cute if I had like 40k followers on my account and I could just like pretend what it would be like to be the famous person I've always imagined I'd grow up to be.

16:19I meet a girl in my creative writing course and I hire her to help me write one line, two line captions for this audience of 40 ,000 bots. I'm buying all the likes per post, which is more realistic to do financially because it was like, I don't know,$1 for like 1 ,000 likes or something fucking crazy like that. And we are churning out this content that no one is reading. It is just going out to robots and robots are liking it. And I get into Cambridge in 2013 and me and this girl more or less like lose touch for the next two to three years while I'm at Cambridge. And it's only once I get to Cambridge that I finally figure out that conundrum that's been stumping me for years, which is how do I marry my interest for Instagram and my like sort of knack for PR?

17:17I begin writing these captions about my life at Cambridge. I actually don't start writing them until the summer after my first year. So like the summer of 2014. It's so funny. I wasn't happy my first year at Cambridge. I always sort of thought, oh, the first year is really hard. It will get better. And that's what sort of kept me going. But it would turn narrator voiceover. Little did she know that first year was the happiest she'd ever be at Cambridge. It really only went downhill from there. It's strange because I was really bullied for my Instagram at Cambridge, but I was also really insecure.

17:53And I also threw these big parties and I didn't really have enough self-esteem. You know, some of the popular kids were really nice to me and were genuinely my friends, but I didn't have enough self-worth to tell the popular kids who weren't nice to me to like fuck off. So like we hung out all the fucking time. They wanted to come to my parties. They wanted me at their parties if only to like see their parties later documented on my Instagram. But all the while they looked down on everything I was doing and the bullying got worse. I had been slowly taking more and more Adderall which is a kind of U.S.

18:29study drug. It's like an amphetamine salt so like it has a similar chemical base as meth. And I'm taking Adderall. And part of what any sort of amphetamine chemical does for your brain is that it induces this fake state of euphoria. And for someone who was like really grappling with untreated clinical depression, the synthetic euphoria of amphetamines really clipped into my brain like a puzzle piece. and it also really fit into like the high stress lifestyle that I was like not cut out for like I don't know how you do it with all the things you do every day like I woke up 90 minutes ago to 20 texts from me being like hi hi hi yeah I wake up I already have like three texts from grace being like have you seen the email I like respond I'm like can you send the email again what email are you talking about?

19:27I don't see any emails. My dream life is really just like a lot more bohemian and structureless. I've luckily now that I no longer have to deal with bullying from my peers and I no longer have to deal with living events to write about. I no longer have to deal with passing the coursework and getting a degree from Cambridge. And I no longer have to deal with building the audience. The audience is built. I've paid my dues online. The audience is there. I can disappear for six months. And when I come back to the internet, all I have to do is like breathe and like someone will write a news story about it.

20:03Like I've got myself to that point. But back then in 2014, 2015, I had to be creating the content. I'd be responding to the comments. I had to be turning in the essays. I had to be going to parties to write about. And so when did that even start? I mean, I have a theory that you're absolutely a businesswoman and I think you know this as well. like the way you started your social media kind of knowing that you needed to buy people co-signing you which were fake but which were there and you know way way way before social media even recognized the value of that but even when you and I want for listeners to outline the way that you found Adderall originally and the you know the fact that you went onto websites for doctors and filtered them by their worst reviews in order to see who would not listen to problems and purely just prescribed medication as a way of getting that end.

20:55You know, my ex best friend who I hired to write those captions for the bots and who would later write that viral tell all about me. She actually gave me my first Adderall. But I, I really see that as just a coincidence. Like, you know, no one blames the bartender who like fixed an alcoholic their first drink. Like no one knows the addiction that that's going to unspool. But as soon as I tried it, I immediately wanted more. But the great news was that I had lived a very drug-free life up until that point. And over the years, I just started getting more and more. Thankfully, my addiction was very handicapped in the early year because I just didn't know where to get Adderall because I didn't have ADHD and I didn't know how to find a sketchy doctor who would prescribe it to me.

21:47and it was very expensive to buy it by the pill. And I was getting really overcharged because I wasn't really like in with the drug dealers of New York City. So I was just like buying it from friends who like only had a few pills to spare. So it was like very hard to come by. And then one day before I left for Cambridge, I had the bright idea to just type in Adderall to the Yelp app and just sort by least stars first. And I read some description that was like, this is the worst doctor I've ever been to. He doesn't even care about your health. He's just prescribing pills. He doesn't even want to hear about your psychological problems.

22:25And I was like, bingo, this is my guy. This is the man for me. Yeah. I was like, that's my guy. I was like, when can I make my appointment? He sounds perfect. And so I went and what do you know, every single time I went to see him, like a new strange tragedy would have befallen him. Like, One time I came in and he just like had shaved off all of his hair, including his eyebrows. One time he had dyed his hair black. The man was wild. What he lacked in normality, he made up for in his ability to give me all the Adderall my addicted little heart could desire. And so once I found him, it was sort of off to the races.

23:10You know, the first time I went to see him, I was very nervous. I didn't have an ADHD diagnosis from like any place ever. I'd never been tested. I felt like I was talking my way into just like 20 milligrams a day. I would have been so happy with. And then, you know, next time I saw him, I just wanted to get it again. And then maybe a few times after that, it was trying to get 30 a day and then 40 a day and then 50 a day. And then I wanted to change that 50 to extended release, which is like stronger than the regular version. And then could I get 60 extended release? And could I get 70 extended release?

23:42And at my peak, I was getting 90 milligrams of extended release per day, which is the legal maximum you are allowed to get in New York City without state diagnosed learning disability. You know, now that I'm saying that, I realize that my source of information on that is actually this doctor. So he could have just totally made that up just to like keep me because he was just like worried that like he was giving me pills that would like stop my heart or something. But I was up to 90 milligrams of XR extended release a day. And then on top of that, buying probably another 90 XR to take per day. And I was still running out like a week before I'd be able to go back to America and refill.

24:24And I was the way I was able to afford my addiction was very businesslike of me. Honestly, I Airbnb'd my apartment in the West Village and it was very beautifully decorated. And I rented it out for like a really great rate, like, I don't know, 250, 350 a night. Like it was a beautiful place and like the heart of the West Village overlooking this gorgeous garden, which like almost never happens in New York. We had such a freakishly huge backyard. Yeah, I would use that money for two things. My addiction, because I need to fly back every month. So you have the cost of round trip flights. That is insane.

25:03I didn't have health insurance, so I'd have to buy the pills. And then I'd have to buy the extra pills to double that prescription while I was there. When you were at Cambridge, what do you feel like you did that really was the inflection point of you turning from someone who had paid for some bots to an actual audience? So when I arrive in Cambridge, I have 40 ,000 followers. I can stay constant at that level and don't post for my entire first year. So this is fall of 2013 into spring of 2014. And it isn't until the summer after my first year. I spent the summer sort of accidentally in Sweden.

25:43And that summer was when I buckled down and I took my account to like 350 ,000. The point is, is that it was the biggest increase I'd ever see in followers. And it all happened that summer. And the way I did it was a two pronged approach. One, I did have to be generating content. In my dream world, I had a posting schedule. I woke up every day of that summer being like, Monday, Wednesday, Friday, I'm going to post. And it never once happened. It was always just like me scraping by because I started telling the story of Cambridge from the beginning. And I did a really great job of not only withholding a lot of information about Cambridge, my whole story of my Instagram, the Cambridge captions, if you will, actually only take place over the span of like 10 days.

26:29There are a few flash forwards and flashbacks and I jump around in time, which then was a very novel concept to do. Instagram was like very much you post in real time about what you were doing. Even if you wait a couple days to post, like you needed to like say throwback Thursday if it like wasn't a real in real time thing. And back in 2014, like a very normal caption would be like, it would be like an aerial photo of your avocado toast. And the caption would be like, hashtag Valencia. And here I was writing like three paragraphs about like how I'm dating this new boy, but sometimes I miss my old boyfriend back in New York.

27:07Like I know that is not the creme de la creme cutting edge of vulnerability today in 2023. Like those same captions posted today wouldn't be anything radical. but you have to believe me when I say that like no one was posting like this in the summer of 2014 and so in addition that was prong one in addition to generating that content I took the other which was then not even half of my Airbnb revenue but that summer since I wasn't spending anything on Adderall I took all of my Airbnb revenue and I put it into buying ads for myself on Instagram And this was years before you had to disclose ads because the concept of influencers and influencer marketing didn't exist yet.

27:54And I would reach out to these accounts on Instagram. And this shows you how far back it was. There wasn't even the messaging function yet within the app. I would have to leave a comment on their photo asking for their email, get their email address, and then get their PayPal. or sometimes they wouldn't even give me their email address and I'd have to use this app called Kick, which was like a messenger app like Telegram. And I would pitch them usually 10 posts for$50. And I was targeting book fandom accounts because I knew that I wanted not just followers, but readers and not just readers, but readers that were predisposed to become obsessed with what they read.

28:32The Fault in Our Stars was really big that summer. The Hunger Games, Gossip Girl fan accounts, Pretty Little Liars, obviously Harry Potter. Like I tried to look for all these book franchises that had fan accounts. And these book fandom accounts would have like, at best, 100 ,000 followers, more like 60, anywhere from like 30 to 80k. And I would buy these, like, all these ads with them. And they truly like thought that I was throwing my money away. They would be like, are you sure you want to do this? And I'd be like, yes. And so I'd look at what adjectives they use when these account owners like something, whether they'd say something was awesome or amazing, what emojis they'd use, how many of the emojis they'd use, what sort of punctuation, how many exclamation points.

29:28And since it wasn't legal yet, I would write in their voice promoting my own account. and then I would have those ads go up at the same time. I would schedule them for when I was finally ready to put up a post. By the time I went back to school that fall, whether I had 350 ,000 followers now or 500 ,000, I was finally at a place where I was getting enough organic likes and had so many followers. At the end of the summer, say Selena Gomez has 3.1. To have 300 ,000 or 500 ,000 as like a normal human being put me in like a very top high performing percentile, even with those 40 ,000 bots taken out of whatever that full number was.

30:14So I was finally getting like enough real likes to start hitting the explore page. And by the time I got back to school that fall, my account was like ready to grow on its own. Like I could still post sporadically, but when I did post, it would get enough real, genuine user interaction that it would qualify for what was then, I think it was called the Discover page or the Explore page. I don't know. Instagram has changed that lingo so much. Yeah. I mean, you can definitely say you have an act for PR. The people building brands at that time, if they had used what you were using then, some of the brands that we don't even see now would be enormous.

30:52How did it get from this point to you having a literary agent? That fall, before I started my second year at Cambridge, I went back to New York because I knew I needed to restock on Adderall before the school year began, but also because I had been able to get an interview with one of the top literary agencies in New York. And the way I actually did that was I called him maybe when I hit like quarter mil followers or something. And I called up his literary agency. And I was like, hello, one meeting, please. I would like to meet with someone because like, I have lots of followers, and I'm a writer, and I would love to have a book deal.

31:32And they all but hung up on me. And before I went back for my second year in late September, before school started in October, I called them back. And I just pretended to be a bitch. I was just like, I'm gonna have to move my meeting on the 27th of September. I can't do 11 a.m. I can really only do three or four. I pretended to be my own assistant and emailed to confirm the meeting to get the address. And then I showed up to his office and I just did the same thing all over again. When he was like, why are you here? I was just very icily like, are you always this unprepared for your meetings or is just this one.

32:12And he was just like blown away. And he signed me, but he said that the followers weren't enough. Like he was like, listen, I see the vision. I think you're a force of nature. I love the writing on the Instagram, but these Instagram followers are not going to move the needle with editors. What you need is mainstream press. So when I went back for my second year at Cambridge, I needed to generate enough content to continue to grow and to keep the account active, but my new priority for book deal was now press. It was to get written about by reporters. How did you get that press? I would Google the words Kardashian Snapchat, and I would sort on Google by news, and then I would see who were the reporters who were among the very first and at the time the only reporters out there who were looking at the Kardashian social media posts and translating like Kylie Jenner's like Instagram story into a news piece and then I would find emails for them or I'd DM them on Twitter from my verified account and I'd just send them the most embarrassing shit you could possibly imagine.

33:23I'd be like, hi there, to whom it may concern, I'm a student at the prestigious Cambridge University and I also have 500 ,000 Instagram followers. I get written about in the Daily Mail and Team Vogue and the Daily Telegraph and Vice and BuzzFeed and places that have like since gone under, but we're really big in 2015. And when I go into my senior year at Cambridge, my goal was just to make it through the year because by now I'm really, really addicted to Adderall. The summer before I'd spent in Sweden writing those captions, but the summer of 2015, I spend just getting high in my apartment in New York.

34:02I just like ditched my boyfriend for the whole summer. We're still together, but I just like my drugs more and my drugs were in New York and like his job kept him in London and I would prefer to be where the drugs are. And when I got back to school, my plan was always, I need this Adderall to make it through my senior year and then I'll address it, just sort of pushing it off until a later date. But I find out when I get back to school, the fall of 2015, for my third year, that my father is in immense credit card debt and he can't pay my tuition. And so because I'm a foreign student, I'm paying like$36 ,000,$38 ,000.

34:41It's just not money that my family had. Like, I'm not from a wealthy family. As much as Natalie, my ex-best friend, would later do a great job convincing other people that I am just this spoiled, privileged bitch, I hire Natalie to help me immediately sell the book. The only way I'm going to come up with 30, 40 grand immediately is by cashing in this Instagram brand that I have built. And I honestly wanted the money as much to support the drug habit as I did for tuition. Like I can sit here and like make it seem like it was all tuition, but like to be so fucking for real with you at that point, I wanted it for the drugs as well.

35:25It's just equal to the tuition, if not maybe just a sliver more. So we spend six weeks buckling down and together we co-write again, 50 % her words and 50 % my words, this document that only publishers see, this book proposal. And in it, we just expand on the Instagram brand. So there's no suicide, there's no depression, there's no addiction. And I don't really stop to think about what I'm doing or what the mistakes I'm making, or I really just want that fucking money. And I want a big check to prove people wrong. I want tuition to stay in school. And I want money for my fucking bills. And those were my priorities.

36:06So we sell a book that I would later, once the dust from that deal had settled I would realize that I had no intention of ever writing it the worst things that have happened to me in my life are not balls and bad hair days and the occasional breakup like that's not the biggest drama and it's not really like what I feel like my purpose as an artist is I really want to write about that darkness so you've you've got a book deal you've received the advance for it it's become very apparent over the next few years that this book is not going to come to fruition. And then at some point following that, Natalie goes to the press with a hugely cutting quote unquote tell all.

36:49What was your initial reaction to hearing that this was going live? I get out of the book deal, but I still owe the$100 ,000. I'm trying to think of ways to pay it back and to tell my audience that I've been dealing with this addiction this entire time that I've also been in these castles. And I plan these creativity workshops where I just try to bring the chaos of me and the brand to life and tell them stories in person. Long story short, a very compelling Twitter thread goes viral that just sort of put side by side ideas that I'd had for the events and things that I'd specifically promised and then photos from the day of without showing how I had offered refunds if people didn't like how the events were shaping up and explained very clearly like what we were doing instead.

37:36And that goes viral. Meanwhile, in LA, Natalie reaches out to the cut and pitches her tell all. And I don't find out about it until that fall. And when I found out that she would be writing this tell all for the cut, she had pitched them on like, give me$5 ,000 and I'll tell you how terrible Caroline Calloway really is. And honestly, I felt like I deserved it. I felt like I was a terrible person during my addiction. Like I was a bad friend. I wasn't responding to texts. I wasn't, I mean, you see how chaotic I am sober. I was even messier. And even though I'd given her$18 ,000 that she kept to help me write the proposal, and even though I felt I paid her a fair wage of$20 an hour to help with captions for the boss, I felt just guilt and shame.

38:24And I wasn't even that angry. And then when it came out and I saw that she had actually taken credit for my work. Not only did she erase my addiction from the record and make everything that I ever did high on drugs seem like my baseline personality, the bigger problem was that she had zoomed over the two to three years where we like fell out of touch. And she, in her story goes, she crafts this really, really conniving narrative where she focuses on us writing captions for the audience of bots and then is very, very vague about when I go off and build the brand alone and write without her the captions about Cambridge that would make me famous and then only hire her again at sort of the 11th hour to sort of like harvest the brand behind the scenes and make this document for publishers.

39:13And on top of that, she really activates this powerful cultural stereotype where she that's really sexist cultural stereotype that's like pretty equals dumb ugly equals smart and even though she's the nepo baby she grew up in the mansion in connecticut i grew up in the hoarder home in virginia like caroline has everything handed to her even though natalie's aunt is like the editor-in-chief of o magazine and like got natalie all her first jobs and natalie was really like popular and charismatic, but she made me seem dumb and manic and stupid and very successfully took credit for all my work. And then two days later, my father's body was found.

39:57What was actually going through your head, going through an enormous media shitstorm, and then almost, I would only assume, all of that being completely dwarfed, which to dwarf your entire career, kind of in your eyes, I'm sure at the time, blowing up in flames, and then to have that happened how did you get through that honestly antidepressants I was so lucky that I had started them I had started them when the creativity workshops went viral that public shaming even though it's like little did I know that I would I was in for like a much bigger shitstorm that was so rough on me and I just felt like so pathetic and such a laughingstock and so hated and so alone I was already in therapy three times a week and I just needed I needed more support.

40:45And so luckily, I'd already been on SSRIs for like fucking six months, and they were doing their thing. And I obviously increased the dosage when both of those events happened. But yeah, it was honestly, it felt surreal, especially since he overdosed by pills. And like Natalie had just like, erased the pill part of my story from this narrative that was being like internationally believed and I was in shock and she'd also done a really clever job by hiding my addiction and making me just seem like a absolutely batshit insane person and like I'm kooky sober so like imagine how much of an off-the-walls lunatic I was on drugs like I'm already like sort of like offbeat and eccentric and like marching to the beat of my own drum on pills, I was a manic pixie nightmare.

41:41And by not mentioning my addiction, she never mentioned my recovery. She made it seem like, you know, I was still the person that I was on pills because I'd always been the person I was on pills because I had never not been that person. She really positioned herself as like the only true authority on my life story and that I was not just an unreliable narrator, but like an incompetent narrator that I was actually incapable of like accurately perceiving my own life story. And it was honestly just complete crisis mode when those two disasters happened back to back, like a one-two punch. She was trying to manipulate, use my father's suicide to like offer her forgiveness and sort of take advantage of me by getting me to like sign over my life rights to her for$15 ,000.

42:30I think I would have just like absolutely crumpled if it hadn't been for the SSRIs. I mean, first of all, I'm so incredibly sorry that that happened. I cannot imagine what to go through all of that at once would have been like. I'm not sure, you know, anyone can. And I'm also not sure how long, if ever, it would take to get over something so soul destroying as for one obviously your father's suicide to get over that to also be processing the rest of it there's so many points in the book that you talk about Natalie and that you talk about the fact that she you know you're you're setting the record straight I think the most powerful thing in setting the record straight was you explaining the story of her having offered you essentially absolution from everything you'd done wrong if you were to accept the offer of$15 ,000 for your life rights coupled with hers when it then later came out that she was to get a million dollars if she were to get you to agree to that in the state that you were recovering from having just found out that your father had died and also this whole situation I mean, to me, you could have just mentioned that in the book.

43:47I would have had opinions. That's just the first page of the book. And you're like, book's over. That's all I need to know about this. That clears everything up. Do you know what's so crazy about grief? We talked for the first time on the phone. She called me a few days after her article came out. It was crazy. When I was posting about my father's suicide, like it got picked up as news. Like the Daily Mail and like the et al covered it. and she called me and I thought she was calling to talk about my father's death and like the phrase that always comes to mind is that she would realize that this wasn't funny anymore which is such a strange phrase to like it's just the one I always come back to again and again because it's exactly what was going through my mind but it implies that at one point she did think it was funny which I don't think I just I just felt like now that you know like this wasn't just about like her like punishing me for like not giving her the other$32 ,000 that she would have gotten for editing the book had I gone through with that book deal.

44:48Like I could understand why she would be like pissed about that. Although as I've gotten older, I understand it less. She just, she's a really like guilt trippy person and like really made me feel like vermin and just like absolute trash all the time. I just thought that like she would want to, I felt like I deserved her punishment. And when she first consoled me about my dad, I thought that's what the conversation was about. And when she offered me that 15 grand and her friendship and her forgiveness and her absolution in return for giving her my life rights, you know, I wasn't even angry. I sort of like, I was so deep in the grief that I was desperate for it.

45:32Like I wanted her to stop hurting me. I wanted her to stop attacking me. I wanted her to stop taking credit for my work. I wanted her to stop making me feel like shit. I wanted love. Like, you know, like my dad had just been taken away and it seemed like a very appealing offer to be totally, totally fucking honest with you. But I was in a crazy place then. That's what was going through my head. but I was really bereaved. I don't think anyone can truly fathom going through something like that having not been through something like that and to be hit with those two things at once very different things but I'm sure very soul destroying in their own ways and I think what's really interesting at this point and I want to finish just talking briefly about the concept of you being a scammer and calling your book scammer and you know you talk about cancellation as being a riptide.

46:20You suggest that people just let themselves, you know, your first instinct is to struggle, but really you should just kind of let yourself be taken by it. And I think what's incredibly interesting about your journey, usually things come with a crying apology video right afterwards. I think you've concentrated on absolution when it comes to refunding people, et cetera. I've seen a lot of that from you. But what's so interesting is it feels like in the same way as you said, you know, there was no memoir for me at home. It feels like there's a memoir for you in being a scammer and yet when you the human side of you also when you're talking about this you still do want to set the record straight like it would be more scammer of you to allow this to be the full narrative and I almost think my interpretation of you calling your book scammer and the kind of quote you use to open the book which is we are only what we pretend to be so we must be careful about what we pretend to be is the fact that I don't think you genuinely believe you're a scammer.

47:21I think it's easier for you to call yourself a scammer and for the reader to tell you back to you that you are not having heard all of these stories from you than it is for you to kind of fight that riptide. I've not stopped thinking about it. I think there's so many different stories that we hear about you and so many different sides of the press and so many different, you know, the, I've always thought that online, the best thing to do when in a difficult situation is always to tell the truth and let people decide. And rather than that, you force the opposite narrative towards people essentially saying, oh no, believe the scammer thing, believe the scammer thing.

47:55It makes sense. Here are all the reasons I'm a scammer. Almost then the reader comes back at you and goes, I understand these are the reasons you're actually not a scammer. I don't know. I find it really interesting when you're then talking about the whole Natalie story because I can so hear the exasperation with it being painted wrong as well. I deal a lot more in just like culture and like fine art, like literal like material art, be it books or visual art. I don't see calling my first book scammer as much of a radical accepting of the brand. I see it as like much more light-hearted and tongue-in-cheek.

48:34Most writers write more than just their first book. They have a long career with many books. And I really see this less as like pinning myself into the scammer narrative forever than not wasting my energy struggling against the narrative that already exists. And in fact, like surfing that wave in order to, as you said, like just tell people the truth and let them decide for themselves. Like I'm not a perfect person and I have lied. I lied on my Cambridge application. Honestly, when I was on Adderall, I was such a little liar. Like I would just do anything for the pills. Like I was also just like not that truthful in my early 20s.

49:11I was like a bit of a Holden Caulfield when it like came to lying. And that's definitely changed now that I'm 31. I feel like within any memoir, you have to tell people the truth in order for them to like make up their own minds. Like I don't see being honest about the ways that I have been imperfect and fucked up as like or or selling that book deal for fucking half a million dollars my senior year of college speaking of fucking up like I've made terrible choices I just think it would be like fundamentally dishonest to expect people to like look at the times when I was like wrongfully accused without give without just being so fucking open and vulnerable and brave with them and being like listen here's everything here's all the info this is the good stuff you didn't know about but there's also like worse stuff about me that you didn't know about I've just tried to quilt it all together in order to just make the best sentences possible like at end of the day it's just all about how compelling can I make this prose and just trying to put that beauty and darkness side by side when you look at your self and you look at your story and look at kind of within you and who you are separate from this, you know, what might feel like a persona sometimes when you, when you are talking about this, you know, all of the things that people have branded you.

50:33Do you think in any way that you are this scammer or is this title more of kind of scammer almost in like quote marks as the thing people have called you? Listen, I've been finding myself saying this on press and I very much stand by it. Like if anyone out there has ever paid for something that they haven't been fully refunded for, if they weren't happy with it, if they had any sort of problems. Like I have pretty shitty customer service. It's just me, but like I'm happy to refund you. And like, I think I've done a pretty good job of like, I've made some spectacular messes in my life, but I've also gone to spectacular lengths to clean them up.

51:12Like I earned back$100 ,000 selling topless photos on OnlyFans and paid back my publishers. I didn't pay rent for a year in New York and I owed$40 ,000 and now I only have$10 ,000 of that left to pay back. Like I do feel like I clean up my messes and I'm very proud of that. And I also feel like none of my messes are criminal. The rent was late. It wasn't like I was never going to pay it. When we talk about like the scammers who loom large on the collective cultural imagination, Billy McFarland, Anna Delvey, Elizabeth Holmes. What do all three of those people have in common that I don't have in common with them?

51:51It's a little thing I like to call federal fucking prison. Like all of those people are like have either been to jail or in jail right now at this very moment or at under house arrest wearing an ankle monitor. And like I do believe in like rehabilitative justice. And I think you should be able to like serve your time and like not be ostracized forever for that. I also think it's very relevant to point out that like I've never done crime. I called my first book Scammer. But do I really think of myself as like a Bernie Madoff wolf of Wall Street? No, of course fucking not. And why don't I think that?

52:27Because I've never done fucking crime. And that's a really big difference between me and like criminals is the crime, you know? I absolutely do know. and I think that you know as I said earlier social media makes things as big as they can make them until they're stopped and I think you having not stopped it by playing into it I think is I can imagine freeing in certain ways for you to be able to kind of reclaim but also I do think rebrands it in that way again and again and I think that the aftermath of a cancellation I don't think if you plotted like the aftermath versus the crime on everything I do not genuinely think there would be any correlation between the severity of the crime or quote unquote crime of like cancellation and the actual like aftermath of it.

53:13I don't think social media works that way. I think it's all about branding and recovery and I think your approach to it has been really interesting. Within the book you say that after writing a book which I know has been a huge part of your life and your aim and your kind of view of success, you say that you might have a few minutes of happiness someday at some point and I've seen through your Instagram receiving positive reviews of the book as genuinely a fantastic piece of writing which I agree I think you are a fucking brilliant writer and I don't think you need me to tell you that you know I texted you saying to use your own words like you write so fucking well and it was a pleasure to read I can tell the excitement and true happiness that you genuinely seem to get out of that Have you yet since publishing this or since having sent this out to journalists and having received positive press, have you yet had that kind of sigh of relief of that feeling of I did it, I completed a memoir, I've got something out there and people think it's art.

54:17Have you had that feeling? Yes, I've totally had that feeling. And like, it's, this is such a wonderful point to circle back to at the end, because I think it really picks up on what we were talking about before when I was like, I don't really expect to be happy in life. I just want to make the best art that I can. I want to make art that outlives me by centuries. And that is remembered long after there are people alive who actually knew me. And like, that is just like, I'm really not focused on the here and now, even though I know we're supposed to be mindful and present and all that stuff, just like, I'm being totally honest, but just seeing like glimmers of during my lifetime of like having achieved that or just even being on my way to achieving that, like three different publications called my first book a masterpiece.

55:03And like one was the Washington Post and another was the stylist. And like, it just makes me so happy. And it really, it does make me happy, Even though I'm not really focused on like sustained happiness, it does make me so happy. And it brings me like the greatest amount of like joy and peace that I've like ever known or expected to know in my lifetime. Well, I wish we could talk forever, but I feel like that is almost the perfect place to end. I feel happy for you. I feel like you probably scheduled your whole day into 30 minute like Pomodoro blocks. and like we are already like three pomodoro blocks or whatever like scheduling blocks over like what you had for like this event and like now your whole day is fucked up and i'm so sorry if that's the case but if we freaky friday'd and we woke up in each other's lives which by the way hollywood if you're listening is a movie i would watch and like i have to be a businesswoman and like you have to be like a bohemian layabout like charlene calloway figure I'd absolutely watch this fucking film in a heartbeat.

56:07And I'm not really sure if you can ever make me be more productive, but maybe there's some solace to be found in the fact that you don't fundamentally find my chaos intolerable. I think there's maybe some self-confidence and self-peace to be found, some serenity to be found in that fact for me. So I'm so happy to finally meet you. And I've admired you from afar for years. someday we'll do a podcast part two where we will talk about our friendship since this moment honestly I feel like we could we genuinely could have the conversation forever I also feel like that is a documentary um putting Caroline on the actual productivity you've been amazing I can't wait to listen to this back I feel like there's so much I need to process and congratulations on the book thank you it's phenomenal and if that was the goal you've done it so I hope you can have that sigh of relief.

56:59Thank you so much. There's honestly nothing kinder that anyone in the world could say to me and I am so happy to finally be friends. And come to Florida. You always have a home here. Bring the dog. I'm sure Matisse in his little broccoli hat would love to meet him. I'm obsessed and thank you so much. Bye!