Once Upon A Con - Episode 3: "Dangling That Carrot"

Release Date: February 19, 2025
Host/Author: iHeartPodcast

1. Introduction

In the third episode of Once Upon A Con, titled "Dangling That Carrot," Caroline D'Amore delves deeper into her tumultuous relationship with David Bloom. Once viewed as a mentor and key to her entrepreneurial success, Bloom's true nature as a con artist begins to unravel, leading Caroline to a path of betrayal, loss, and determination to seek justice.

2. The Illusion of a Mentor

Caroline D'Amore recounts how she initially perceived David Bloom as the ideal mentor who could elevate her business, Pizza Girl Pasta Sauce, to new heights.

• Caroline D'Amore [02:14]:
  "Several times, Caroline would say to me in tears that I thought this was my chance to be lucky. I thought this was my chance for someone to save me."

Caroline invested her personal savings and convinced her loved ones and business partners to contribute a combined $35,000 to Bloom for what was presented as the Soho House IPO.

• Caroline D'Amore [02:34]:
  "I empty my bank account of all the cash I have and get my loved ones and business partners to fork over a combined $35,000 to David Blum for that Soho House IPO."

Bloom further lured Caroline by offering to invest $2 million of his own funds into her company, solidifying his position as a central figure in her business endeavors.

3. The Golden Opportunity

Bloom's influence extended to connecting Caroline with A.C. Gallo, the CEO of Whole Foods, which promised a monumental breakthrough for Pizza Girl Pasta Sauce.

• Caroline D'Amore [05:14]:
  "David calls up Whole Foods CEO A.C. Gallo, and I'm right there beside him, freaking out."

Caroline describes the excitement of potentially having her product featured in 500 Whole Foods stores nationwide, marking what seemed like the pinnacle of her entrepreneurial journey.

4. The Austin Trip and Vanishing Act

In late August 2021, Caroline and her business partners, Beck and Erin, flew to Austin, Texas, to solidify the partnership with Whole Foods. However, what was supposed to be a defining moment turned into a nightmare.

• Caroline D'Amore [11:18]:
  "David knew that this is a baby startup and that we can't be spending money that we, you know, shouldn't be spending. We're sitting in Texas, and all of a sudden, it's the next day, and David wasn't there."

Initial delays were attributed to other high-profile meetings, including one with the head of Netflix, Ted Sarandos. Despite these excuses, the lack of clarity about the meeting's expectations and Bloom's evasive behavior raised red flags.

5. The Discovery of Deception

While waiting in Austin, Beck stumbled upon alarming information about David Bloom's past, revealing his history as a con artist.

• Caroline D'Amore [20:33]:
  "Just found this article on by just Googling David Bloom scammer. We're just standing on the bridge after five days in Austin waiting for this mysterious meeting to happen."

The revelation that Bloom had been involved in various scams since the 1980s shattered Caroline's trust. She realized that the promised IPO and connections were fabrications designed to exploit her and her partners financially.

• Caroline D'Amore [21:55]:
  "Apparently, David Bloom has a long history of scamming a lot of people. I mean, we found news reports about his cons that go all the way back to the 1980s."

6. Turning the Tables

Overwhelmed by grief and regret, Caroline decided to take action. Determined not to be another victim, she and her partners devised a plan to expose Bloom's deceit.

• Beck [34:15]:
  "To call, record him while we're in Texas. And we need to get him to say, talk about A.C. Gallo, talk about the meeting. You have to say, but I've been here five days. Every fact you can put in there that he can confirm that he set up for you, then we've got him admitting that he did all that stuff."

Caroline began documenting Bloom's inconsistencies and falsehoods, preparing evidence to present to the authorities. Her determination was fueled by the realization that Bloom's manipulation had not only drained her finances but also strained personal relationships, including her breakup with Ryan, who had also invested his family's money based on Bloom's assurances.

• Caroline D'Amore [25:01]:
  "Five nights in Austin. Five nights we've been sitting here in Austin because we thought our lives were going to change. Oh, my God."

7. The Commitment to Justice

Caroline's emotional journey culminates in her decision to confront Bloom directly and involve law enforcement, ensuring that he can no longer exploit others.

• Caroline D'Amore [36:12]:
  "David Blum promises us the moon and we record it all for police. He just thinks I'm just a freaking dummy."

Her resilience and commitment to justice not only serve as a testament to her strength but also aim to protect others from falling prey to similar scams orchestrated by Bloom.

8. Conclusion

"Dangling That Carrot" showcases the perilous allure of mentorship in the business world and the devastating impact of trust misplaced. Caroline D'Amore's story is a powerful reminder of the importance of due diligence and the courage required to confront and overcome betrayal.

Notable Quotes

• Caroline D'Amore [02:34]:
  "I empty my bank account of all the cash I have and get my loved ones and business partners to fork over a combined $35,000 to David Blum for that Soho House IPO."

• Caroline D'Amore [05:14]:
  "David calls up Whole Foods CEO A.C. Gallo, and I'm right there beside him, freaking out."

• Caroline D'Amore [20:33]:
  "Just found this article on by just Googling David Bloom scammer. We're just standing on the bridge after five days in Austin waiting for this mysterious meeting to happen."

• Caroline D'Amore [25:01]:
  "Five nights in Austin. Five nights we've been sitting here in Austin because we thought our lives were going to change. Oh, my God."

• Caroline D'Amore [36:12]:
  "David Blum promises us the moon and we record it all for police. He just thinks I'm just a freaking dummy."

Reflections and Insights

This episode serves as a cautionary tale about the vulnerabilities entrepreneurs face when seeking mentorship and investment. It underscores the necessity of thorough background checks and maintaining skepticism, even when opportunities appear golden. Caroline's journey from hope to betrayal, and finally to empowerment, provides invaluable lessons for anyone navigating the complexities of business partnerships.

Listen to Once Upon A Con Season 1 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts to uncover more about Caroline D'Amore's quest for justice against David Bloom.