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May 19, 2025 8 mins

Oscar Health NYSE (OSCR) was supposed to revolutionize health insurance. Instead, it became a poster child for unprofitable tech IPOs; burning through cash and investor goodwill like kindling. But something weird happened on the way to irrelevance: the business quietly started working. Real profit. Better margins. Grown-up leadership. In this episode, I dive deep into Oscar’s transformation. What’s real, what’s still risky, and whether the market is missing the plot. No hype. Just an honest breakdown of a company that might not be a joke anymore.


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