Too Many Tabs Podcast: Caroline Calloway: A Captioned History

Episode: Caroline Calloway: A Captioned History | Too Many Tabs Podcast
Release Date: December 8, 2024
Hosts: Pearlmania500 (Pearl) and Mrs. P

Introduction

In this compelling episode of Too Many Tabs, hosts Pearlmania500 and Mrs. P delve deep into the enigmatic rise and controversial fall of Caroline Calloway, an Instagram influencer turned literary figure. Stripping away the glitz and glamour of social media fame, the duo unpacks the intricate web of ambition, deception, and the quest for authenticity that defined Calloway's public persona.

Caroline Calloway's Rise as an Instagram Influencer

Pearl (Host 1) begins by tracing Calloway's early endeavors on Instagram. Starting her account in June 2012, Calloway sought to carve a niche by coining the hashtag #AdventureGrams, sharing curated images of her travels and social exploits.

[19:22] Pearl: "She created hashtag #AdventureGrams. That's so cool. This is only 12 years ago."

Calloway's strategy was multifaceted:

• Buying Followers: In 2012, she admitted to purchasing 40,000 followers for just $4.99, a tactic that smiles back in today’s influencer economy.

  [16:40] Mrs. P: "She bought her first 40,000 followers for $4.99."

• Targeted Advertising: She invested in Instagram ads, specifically targeting Harry Potter and young adult (YA) novel fan accounts, effectively expanding her follower base to over 500,000 by 2015.

[26:17] Mrs. P: "She targeted almost every post towards users that followed Harry Potter or YA novel fan accounts."

Calloway meticulously crafted her online image, blending romanticized British aesthetics with American charm, reminiscent of shows like Emily in Paris.

Securing a Book Deal and Withdrawal

With a substantial following, Calloway aimed to transition from social media to publishing. In 2015, she secured a $375,000 book deal with Flat Iron Books, intending to capitalize on her online fame.

[31:54] Pearl: "In 2015, Caroline Calloway signed a book deal with Flat Iron books for $375,000."

However, Calloway's ambitions were overshadowed by personal struggles:

• Forged Transcripts: To gain admission into Cambridge, she falsified her school transcripts, manipulating grades to present herself as an exceptional student.

  [29:04] Pearl: "She forged her transcripts...getting a book deal under false pretenses."

• Adderall Addiction: Reports emerged of her deepening Adderall addiction, which compounded her inability to deliver on her literary promises.

[32:00] Mrs. P: "While this was happening, Calloway was reportedly descending into a deep Adderall addiction."

As deadlines loomed, Calloway's inability to produce the promised manuscript led to turmoil, ultimately resulting in her pulling out of the book deal in 2017. This decision not only left her owing $100,000 to Flat Iron Books but also tarnished her reputation among her followers.

The Workshop Debacle

In 2018, Calloway attempted to reinvent herself by launching a series of personal workshops aimed at teaching writing, personal branding, and wellness. Leveraging her Instagram following, she sold out multiple events through Eventbrite without adequate planning or resources.

[34:09] Pearl: "She collected money for tickets and quickly sold out many of the US tour dates. But she hadn't booked event spaces or hired photographers."

The execution was disastrous:

• Massive Overestimation: Booking 1,200 mason jars for mini gardens overwhelmed her West Village apartment.
• Culinary Failures: Promising homemade salads, she found herself unable to cater for 50 people the night before each event.
• Broken Promises:
  • Handwritten Letters: She abandoned the idea, citing delays.
  • Orchid Crowns: Replaced with clip-in flowers due to time constraints.

[36:15] Pearl: "She promised homemade salads but realized cooking for 50 people the night before an event was impossible."

The resulting chaos led to widespread online backlash, drawing comparisons to infamous scams like Fyre Fest.

Media Scrutiny and Falling Out

Calloway's missteps didn't go unnoticed. Natalie Beach, a former friend and collaborator, penned a revealing essay in The Cut detailing their tumultuous relationship and exposing Calloway's manipulative tendencies.

[54:06] Mrs. P: "Natalie Beach wrote in The Cut, 'When I first met Carolyn Calloway, all I saw was the beginning of something extraordinary.'"

Key revelations from the essay included:

• Emotional Manipulation: Calloway often demanded attention and assistance without reciprocating.
• Deceptive Practices: Instances like stolen Yale plates were questioned for their authenticity.
• Ghostwriting: Beach acted as Calloway's ghostwriter, highlighting the uneven dynamic in their collaboration.

This exposé ignited a viral discussion online, leading to a swift decline in Calloway's fanbase and the defunding of dedicated fan accounts.

[59:52] Pearl: "Everyone on the Internet was talking about the plates along with all the other stuff, but the plates really did get memeified."

Subsequent Ventures and Attempts at Redemption

Undeterred by the backlash, Calloway sought alternative revenue streams:

• Art Sales: She began crafting and selling replicas of Matisse's "Blue Nudes", branding them as interpretative art pieces.

  [67:04] Mrs. P: "She starts crafting this art and selling it to her followers for a couple of hundred bucks a piece."

• OnlyFans Account: Named "Only Scams", she offered "cerebral softcore porn" dressed as characters from Ayn Rand's "Atlas Shrugged".

  [72:02] Pearl: "She's selling bottles of facial oil...and then she creates an OnlyFans account, which she calls 'Only Scams,' featuring photos of her topless cosplaying as Dagny Taggart."

• Hurricane Diary: In October 2024, during Hurricane Milton, Calloway decided to document her experience rather than evacuate, further blurring the lines between personal crisis and performative content.

  [86:23] Pearl: "In October 2024, Carolyn Calloway made news again because she decided to ride out Hurricane Milton rather than evacuate."

Despite these efforts, her ventures were met with skepticism, with critics labeling them as desperate attempts to regain lost ground rather than genuine initiatives.

Final Thoughts and Conclusions

Throughout the episode, Pearl and Mrs. P grapple with the complexities of Calloway's actions:

• Intent vs. Mental Health: They ponder whether Calloway's failures were deliberate scams or symptoms of a deeper mental health crisis.

  [45:00] Pearl: "I don't think it was a scam. I think she's just having a mental health crisis situation and didn't understand the heavy lift that it is."

• Impact on Followers: The duo underscores the detrimental effects of Calloway's actions on her audience, who invested time and money into her perceived authenticity.

• Reflection on Social Media Fame: The episode serves as a critique of the influencer-driven attention economy, highlighting how visibility can be manipulated and the fragility of online personas.

[80:17] Pearl: "It's stealing time and attention from you... that's just as bad as other scams."

In closing, Pearl emphasizes the importance of critical engagement with online personalities, urging listeners to discern genuine content from performative deception.

[90:12] Pearl: "She is a reflection of the Internet and the times. An embodiment of the BuzzFeed-esque scammer."

Notable Quotes

• [19:22] Pearl: "She created hashtag #AdventureGrams. That's so cool. This is only 12 years ago."
• [16:40] Mrs. P: "She bought her first 40,000 followers for $4.99."
• [31:54] Pearl: "In 2015, Caroline Calloway signed a book deal with Flat Iron books for $375,000."
• [45:00] Pearl: "I don't think it was a scam. I think she's just having a mental health crisis situation and didn't understand the heavy lift that it is."
• [80:17] Pearl: "It's stealing time and attention from you... that's just as bad as other scams."

Conclusion

This episode of Too Many Tabs offers a thorough examination of Caroline Calloway's journey through the treacherous waters of social media fame, ambition, and personal unraveling. Through detailed analysis and poignant reflections, Pearl and Mrs. P shed light on the broader implications of influencer culture and the vulnerabilities it exposes in both creators and audiences.

For listeners keen on understanding the dynamics of digital personas and their real-world repercussions, this episode serves as a cautionary tale and a call for more authentic engagement in the ever-evolving online landscape.