In the debut episode of The Long Short Way, Rabbi Mendy Bistritzky speaks with Jonathan Schwartz, a former Hollywood business manager who once had it all—until a secret gambling addiction drove him to steal over $7 million from celebrity clients, including Alanis Morissette. His story made national headlines, but the public scandal was only part of a much deeper unraveling.
Jonathan opens up about the dual life he was living: embezzling funds, gambling recklessly, and using drugs—all while outwardly attending synagogue and trying to keep up appearances. After hitting rock bottom and serving time in federal prison, Jonathan began a path of true t’shuva—Jewish repentance—not just as an abstract idea, but as a daily, humbling practice of change. This conversation explores the pain of self-deception, the cost of broken trust, and the redemptive power of faith, community, and spiritual honesty.
To get in touch with Jonathan, find him on Instagram at @therealjonathanschwartz
Support this podcast by donating here: https://donorbox.org/chabad-of-saugus
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
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