Once Upon A Con

iHeartPodcasts
  • 3.8 (446)
  • TRUE CRIME
  • WEEKLY SERIES
Once Upon A Con

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.

Season 1

  1. EPISODE 1

    Episode 1 - He Thinks I’m a Masseuse

    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. See omnystudio.com/listener for privacy information.

    36 min

  2. EPISODE 2

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

    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. See omnystudio.com/listener for privacy information.

    27 min

  3. EPISODE 3

    Episode 3 - Dangling That Carrot

    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. See omnystudio.com/listener for privacy information.

    27 min

  4. EPISODE 4

    Episode 4 - The Best Friend You Never Asked For

    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.  See omnystudio.com/listener for privacy information.

    30 min

  5. EPISODE 5

    Episode 5 - He Loves Me So Much

    Nancy Ozeas was married to David Bloom for nine years. They enjoyed an extravagant lifestyle together, residing in their $1.6 million loft in Venice Beach and taking exorbitant vacations all over the world. David paid for everything. Or at least, that’s what he led Nancy to believe. But one day when she finds a stack of bills from creditors demanding payment from her, Nancy suddenly realizes - David Bloom had actually stolen her identity to fund their entire life together. See omnystudio.com/listener for privacy information.

    36 min

  6. EPISODE 6

    Episode 6 - He Will Not Stop Until He Kills Me

    Caroline is shocked to learn that not only was she scammed by David Bloom, but many of her neighbors in their apartment building were also ripped off by the con man. Nearly out of funds and desperate to find answers, Caroline organizes for a group of David's victims to come together and confront the "Wall Street Whiz Kid."  See omnystudio.com/listener for privacy information.

    33 min

  7. EPISODE 7

    Episode 7 - Jumping Through Hoops Like Circus Animals

    Caroline and a group of David Bloom’s most recent victims knock on his apartment door. He greets them, with an egregiously calm demeanor. There's yelling, there's crying. Caroline unloads all the pain and fury she's been harboring against the man she once considered a mentor and friend. David is soft-spoken and apologetic, and claims the accusations have all been a misunderstanding. He promises to return everyone's money. See omnystudio.com/listener for privacy information.

    29 min

  8. EPISODE 8

    Episode 8 - Nobody Knows Which End is Up

    David Bloom, forcefully accompanied by a group of his victims, goes to the bank to retrieve a fraction of what he owes. Despite bilking hundreds of thousands of dollars from his friends and neighbors, David only manages to come up with $20,000 to partially pay them all back. Police are called, and David gets arrested. But he quickly makes bail and is released from custody. And to everyone's surprise: David is not charged with any crime. See omnystudio.com/listener for privacy information.

    29 min

  9. EPISODE 9

    Episode 9 - This Guy Has Eras

    Caroline speaks at a press conference with CA District Attorney George Gascon after David Bloom is charged with 18 felonies. Caroline and L.A. Times writer James Queally discuss everything about the case, from how slow the process is to what a possible plea bargain could be. Caroline and James hope their publicization of Bloom’s crimes puts an end to his trail of deception. But will this con artist ever change? See omnystudio.com/listener for privacy information.

    26 min

  10. EPISODE 10

    Episode 10 - I Hope You Find Peace One Day

    Two years after her own experience, Caroline meets another one of David Bloom's victims. Sean Kushner was a sleep-deprived, new father who was promised a house in a trust, luxury trips, and even a meeting with the President. The impact from the experience is significant, and ultimately leads Sean to refocus on what truly matters. See omnystudio.com/listener for privacy information.

    26 min

  11. SEASON 1 TRAILER

    Introducing: Once Upon A Con

    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. See omnystudio.com/listener for privacy information.

    2 min

Trailer

3.8
out of 5
446 Ratings

About

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.

Information

  • Channel
    iHeartPodcasts
  • Creator
    iHeartPodcast
  • Episodes
    11
  • Seasons
    1
  • Rating
    Explicit
  • Copyright
    2025 iHeartMedia, Inc. © Any use of this intellectual property for text and data mining or computational analysis including as training material for artificial intelligence systems is strictly prohibited without express written consent from iHeartMedia
  • Show Website
    Once Upon A Con
  • Provider
    iHeartMedia + Entertainment, Inc

More From iHeartPodcasts

You Might Also Like

To listen to explicit episodes, sign in.

Stay up to date with this show

Sign in or sign up to follow shows, save episodes, and get the latest updates.
Select a country or region

Africa, Middle East, and India

Asia Pacific

Europe

Latin America and the Caribbean

The United States and Canada