Caroline and her business partners begin to wrap their heads around David Bloom’s real occupation: Full-time Scammer. He’s been a con artist ever since he was a teenager. He scammed his parents. He scammed his friends. He scammed everyone with fake investments that were nothing more than Ponzi schemes to fund his exorbitant lifestyle. No one would know better than David's ex-wife, who suddenly surfaces with a truly shocking account of what it was like to be married to a charlatan. 

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Caroline and her business partners arrive in Austin, excited to have their first meeting with Whole Foods CEO A.C. Gallo the very next morning. Caroline’s already talked to him during a phone call set up by David, and she’s giddy with anticipation. But suddenly, the meeting gets pushed. And then it gets pushed again. And again. And again. Five days later, Caroline makes a shocking discovery about David and the man she met on the phone.

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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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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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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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