Episode Details

Hims & Hers CFO Oluyemi Okupe quietly cashed out over $3 million in stock via a pre-set, automated plan — not a sign of doubt, but a tax-smart move. He still owns hundreds of thousands of shares and is locked into the company’s future. What really matters? The business’s shifting strategy — leaning into weight loss drugs and global markets — is squeezing margins, as confirmed by recent earnings. Executives selling stock don’t tell you everything; watch the numbers and the direction, not the headlines.

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