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A Gem Of A Story

Comic Bryan Sobolewski's Family Jewels podcast discusses his real life multimillion dollar crimes, prison and quest for redemption.

by Chuck king

DELRAY BEACH – Bryan Sobolewski launched a stand-up comedy career to help sell a book.

He started a podcast with hopes it would lead to a one-man show.

That his stand-up and the podcast started as, essentially, promotional vehicles doesn’t diminish the intrigue of either – especially for fans of comedy and true crime drama.

It’s easy to understand why Sobolewski wrote a book. His life story reads like a potential best seller.

In the early 1990s he, his father John and brother Kevin established a jewel theft ring based in the northeast to have stolen gems with an estimated value of as much as $2.6 million across multiple states over several years.

Sobolewski ultimately served three years in prison.

Learning that few businesses were willing to hire an ex-con, Sobolewski set about writing a book detailing his experiences. After unsuccessfully shopping the book to publishers, Sobolewski self-published Family Jewels: A Father/Son Story.

To support the book, he did a series of public speaking engagements – often to high school groups – aimed at keeping people from making the same mistakes he did. He also decided to give stand-up comedy a try, doing so for about a decade in Boston.

“I thought the comedy stage would be another way to promote the story and potentially market the book,” Sobolewski said. “When I realized the book wasn’t going to be a big smash success I just kept doing comedy because I loved it. I loved the uniqueness of my story on the stage.”

After a few years away from comedy, Sobolewski moved to Florida three years ago and relaunched his comedy career. With the encouragement of fellow Boston comic Brian Glowacki, Sobolewski also created the Family Jewels podcast (above).

It’s far from a typical comics-telling-jokes or comics-interviewing-comics podcast.

In Season I, Sobolewski walks listeners through the details of his family’s crime spree, robbery by robbery, offering insight into a family dynamic that could benefit any Netflix crime drama.


Season II, which is coming to a close, picks up following the arrest of Sobolewski’s father and includes Brian’s time in prison.

Season III will focus on Sobolewski’s attempt to put his life back together following his release from prison.

Each podcast is at least 30 minutes long (most are closer to an hour). They drop every Sunday. In the earliest editions Sobolewski would conclude with some stand-up bits – a la early Seinfeld episodes – but he eventually dropped that segment to avoid repetition.

“I record it in my closet with all my couch cushions surrounding me so I try to get the best quality,” Sobolewski said.

Sobolewski’s not certain what Season IV will entail, but he envisions the Family Jewels podcast turning into something of a criminals-in-cars-talking-crime-type show.

Ultimately, he wants the first three seasons to form the basis of a potential comedic one-man-show.

To that end, Sobolewski is also using his stand-up performances to try to identify the funniest parts of his life story in an attempt to narrow the focus for that show.

He’ll perform just about anywhere – Glowacki added Sobolewski to his show at Laugh In in Fort Myers earlier this summer – but recently Sobolewski appears to have found a home base at the Doghouse Theater in Delray Beach.

Most every Friday Sobolewski is one of the local comics who performs a stand-up set, then sits back and watches the Sick Puppies improv troupe perform skits based on what they just heard.

“They’re calling me their Friday headliner,” Sobolewski said. “And they are just letting me go up and riff on my life stories to try to develop and pick out which stories will be in the one-man show.”

Sobolewski hopes his performances drive the audience to his Family Jewels podcast.

“The podcast adds credibility because they walk away from the show and they have fun, and if they want to check out the podcast they can hear the full story,” Sobolewski said.

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