Once Upon a Con: Episode 4 - The Best Friend You Never Asked For Release Date: February 26, 2025 Host/Author: iHeartPodcast

Introduction

In Episode 4 of Once Upon a Con, titled "The Best Friend You Never Asked For," host Caroline D'Amore delves deeper into her harrowing experience with David Bloom, a seasoned con artist known as the “Wall Street Whiz Kid.” This episode chronicles Caroline's journey from betrayal to determination as she uncovers David's intricate schemes and takes actionable steps to bring him to justice.

Recap of Previous Events

The episode opens with a brief recap of the series' earlier episodes, setting the stage for Caroline’s confrontation with David Bloom. Caroline and her business partners, Beck and Erin, had initially believed David to be a trustworthy mentor. However, mounting delays and inconsistencies revealed his true nature as a fraudster who had swindled them out of $35,000 connected to the Soho House IPO.

The Revelation of the Scam

Caroline narrates the discovery of David Bloom’s deceit:

Caroline D'Amore [02:22]: "Next month, my business partners and I fly to Texas for a meeting David Blum set up that's going to make Pizza Girl pasta sauce a national brand."

As plans faltered, suspicions grew:

Beck [03:54]: "Let's not forget that David Bloom was a professional con artist. He had been doing this for 30 years. We didn't know it at the time, but, you know, looking back, this is what he does."

Emotional Impact on Caroline

The emotional toll on Caroline becomes evident as she shares her personal struggles:

Caroline D'Amore [05:01]: "I was carrying a weight that no one else in that room had to carry because I truly feel responsible. Right. For Ryan, for you guys."

She candidly discusses her mental health challenges triggered by the betrayal:

Caroline D'Amore [05:38]: "I was having suicidal thoughts. Like for a little bit of time after that, I was having a really hard time."

Gathering Evidence

Determined to expose David, Caroline and her team begin collecting evidence. They start recording David's phone calls, capturing incriminating admissions of his fraudulent activities.

Caroline D'Amore [06:43]: "So Beck, Aaron, and I start recording all of David Bloom's phone calls from that point on, and I get him to confirm every single scam he's ever pulled on me."

Devising a Plan to Expose David

To outmaneuver David, the team formulates a strategic plan:

Caroline D'Amore [12:06]: "Now the tables are turned. Like, he doesn't know that you know, and now you're playing him so that he can get his just rewards."

They create a facade to avoid raising David’s suspicion while continuing to gather vital evidence.

Background on David Bloom

The episode provides an in-depth look into David Bloom’s history, revealing his long-standing role as a con artist:

James Quealey [19:08]: "David Bloom’s origin story traces all the way back to the wealthiest parts of Manhattan. He grows up really wealthy, Upper East Side Manhattan, vacations in the Hamptons, and he starts this investment group that was basically the beginnings of what would become his grift of choice."

David’s early exploits include running the Greater Sutton Investor Group, amassing millions from unsuspecting investors through false statements and deceptive practices.

David's History and Previous Scams

David’s criminal endeavors span decades:

Caroline D'Amore [20:26]: "David Blum makes a literal fortune early on in his career of conning."

He successfully executed a Ponzi scheme in the 1980s, defrauding clients like Elizabeth and her husband out of $150,000, only to face conviction and imprisonment. Despite his incarceration, David resurfaced multiple times, continuing his fraudulent activities under different aliases.

Continued Scamming in Los Angeles

After his release, David relocated to Los Angeles, where he targeted local bartenders and aspiring actors with promises of lucrative investments and exclusive opportunities:

James Quealey [33:49]: "Bloom is a very talented manipulator. He's been convicted of doing this twice. And he's got so many other people in so many positions of power."

David employed sophisticated tactics, leveraging high-profile connections and appealing to individuals' aspirations to secure substantial investments.

Personal Accounts from Victims

Victims describe David’s manipulative charm and strategic deceit:

James Quealey [35:50]: "Everyone wants to be on the ground floor or something. Everybody wants to get the new gadget. Everybody wants to get the leg up that somebody else doesn't."

Caroline shares how David's manipulations extended to her personal life, tarnishing her reputation and isolating her from the community:

Caroline D'Amore [18:35]: "By the time I got back, David had already told everybody that I was unstable, that I was an alcoholic and a drug addict."

Caroline's Determination and Next Steps

Despite the emotional and financial devastation, Caroline remains resolute in her mission to expose David:

Caroline D'Amore [06:26]: "I'm not gonna let this lying asshole get away with this. I'm now in, like, at this stage. Like, I already went through my crying, and now I'm in the stage of, like, I just want to get this motherfucker."

With solid evidence in hand, including recordings of David’s admissions, Caroline prepares to collaborate with law enforcement to ensure David faces justice.

Conclusion

Episode 4 of Once Upon a Con masterfully weaves Caroline D'Amore’s personal ordeal with a broader narrative of systemic fraud perpetrated by David Bloom. Through emotional honesty and meticulous investigation, the episode not only highlights the devastating impact of scams but also underscores the resilience required to combat such deceit. Caroline’s unwavering determination serves as an inspiring testament to seeking justice against powerful adversaries.

Notable Quotes

• Caroline D'Amore [05:01]: "I was carrying a weight that no one else in that room had to carry because I truly feel responsible."
• Beck [03:54]: "David Bloom was a professional con artist. He had been doing this for 30 years."
• Caroline D'Amore [06:43]: "I get him to confirm every single scam he's ever pulled on me."
• James Quealey [19:08]: "David Bloom’s origin story traces all the way back to the wealthiest parts of Manhattan."

Key Takeaways

• David Bloom’s Tactics: Mastery in manipulation, leveraging high-profile connections, and exploiting victims’ aspirations.
• Emotional Resilience: Caroline’s journey emphasizes the psychological toll of betrayal and the strength needed to overcome it.
• Systemic Fraud Awareness: The episode sheds light on the importance of vigilance and due diligence in financial dealings to prevent falling victim to similar scams.

For more insights and developments in Caroline’s quest for justice, stay tuned to Once Upon a Con on the iHeartRadio app, Apple Podcasts, or your preferred podcast platform.