Out of Patients EP421: Oy Vey! It's Libby Amber Shayo
When I invited Libby Amber Shayo onto *Out of Patients*, I knew exactly what I was getting: a walking, talking GenZ Jewish time capsule with a theater degree, a viral alter ego named Sheryl Cohen, and enough camp trauma to get a standalone diagnosis. But what I *got* was a masterclass in comedy as cultural resistance.
Libby is a force. Not because she performs. Because she *witnesses*. She documents the chaos. Repackages pain into punchlines. Carries her Jewish identity out loud in a digital world built to erase it. We talked about COVID courtship, Facebook yentas, influencer fatigue, digital antisemitism, and how playing a nun on stage while running Chabad in real life turned her into the Hannah Montana of Upstate New York. We unpacked why TikTok gave her a platform but grief gave her purpose. We even found common ground in the rage and resignation of watching an entire generation learn about Judaism from hashtags and hate speech.
You’ll laugh. You’ll roll your eyes. You’ll probably start following her by the end. And maybe, like me, you’ll be reminded that satire is still a sacred tool for survival.
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Matthew Zachary
Producer
Matthew Zachary never planned on becoming a healthcare advocate. At 21, while training to be a concert pianist, he was diagnosed with brain cancer and told he might never play again. That was nearly thirty years ago. Spoiler alert - he survived! Instead of returning to the recital hall, he set out to change the healthcare system that nearly broke him.
In 2007, Matthew founded Stupid Cancer, a groundbreaking nonprofit that gave young adults with cancer something they’d never had before: a voice, a community, and the freedom to be angry. Through national conferences and online platforms, it helped millions of patients and families find connection and purpose in the face of isolation.
That same year, he launched The Stupid Cancer Show, the first talk radio program to cover the patient experience with the urgency of breaking news. It later evolved into Out of Patients, his award-winning podcast known for its honest conversations and unapologetic tone. His media work also includes the acclaimed documentary The Cancer Mavericks, which tells the story of the rebel patients who helped transform modern oncology.
Today, Matthew leads Matthew Zachary Worldwide, a media and consulting company that helps brands and organizations better understand the real needs of patients and how to co-create solutions with them, not just for them. His upcoming book, We the Patients: A Field Guide to Surviving American Healthcare (Wiley, June 2026), draws on three decades of lived experience and advocacy to help readers navigate and challenge the U.S. healthcare system.
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Out of Patients EP422: Reenactments, Rants, and Really F*cked Up Insurance
