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Once Upon A Con

Once Upon A Con

Written by: iHeartPodcast
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Caroline D'Amore thought she'd found a mentor in David Bloom, a self-proclaimed power player with ties to some of the world’s most influential CEOs. But her excitement quickly turns to betrayal when David’s complex scheme to defraud her and others out of nearly a quarter of a million dollars is exposed. Determined to seek justice, Caroline takes matters into her own hands and turns the tables on the man once known as the “Wall Street Whiz Kid.” Who is David Bloom – and will he ever pay for his crimes? Find out on Season 1 of Once Upon a Con.

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Episodes
  • Introducing: Once Upon A Con

    Introducing: Once Upon A Con
    Feb 5 2025

    Who is “Wall Street Whiz Kid” David Bloom? Caroline D’Amore learned the hard way after the master conman orchestrated an elaborate scheme to defraud her and many others out of nearly a quarter of a million dollars. Season 1 of Once Upon a Con follows Caroline as she turns the tables on David in an unexpected game of cat and mouse.

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    2 mins
  • Episode 1 - He Thinks I’m a Masseuse

    Episode 1 - He Thinks I’m a Masseuse
    Feb 12 2025

    Caroline D’Amore has spent her life on the periphery of stardom. She’s done small roles in TV shows and movies. But struggles with drugs, a messy divorce, and even a run-in with notorious sex abuser Jeffrey Epstein have kept her fighting to eke out an existence for herself. Then suddenly, a friendly new neighbor enters the picture offering to help Caroline with EVERYTHING.

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    36 mins
  • Episode 2 - If You Live in Hope, You Die in S**t

    Episode 2 - If You Live in Hope, You Die in S**t
    Feb 12 2025

    David Bloom is a silver-haired father figure type. He quickly develops a close bond with Caroline after moving into her storied Hollywood apartment complex. He presents himself as a real titan of industry and very, very wealthy. Caroline is strapped for cash so David offers her an investment opportunity she can't pass up. He also offers to help get Caroline's organic Pizza Girl sauce onto the shelves of Whole Foods supermarkets across the country. After all, he says he's good friends with the CEO. So Caroline and her business partners fly out to Texas with plans to meet the CEO and secure a life-changing deal.

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    27 mins
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