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Hims & Hers bets $250M on its own stock—but will investors follow?

A $250M gamble to revive its sinking stock. But with insider sales and sky-high valuations, can Hims & Hers win back skeptical investors?

Here on the right a man is resting his hand on the chart. There is a bottle in the middle.
Here on the right a man is resting his hand on the chart. There is a bottle in the middle.

Hims & Hers bets $250M on its own stock—but will investors follow?

Hims & Hers Health has announced a bold move to buy back $250 million of its own stock over the next three years. The decision comes as the company’s share price has dropped sharply, losing nearly 30% in just one month. Leadership insists the market has undervalued the business, despite concerns from investors.

The board approved the new $250 million repurchase plan on November 17, 2025. This follows a previous $100 million buyback that failed to stop the stock’s slide. Company executives argue the current stock market price does not reflect the true worth of Hims & Hers.

Just two days later, the company’s CFO, Oluyemi Okupe, sold 23,187 shares at an average of $36.81 each. The sale occurred even as Okupe exercised stock options, raising questions about internal finance and confidence. Meanwhile, the firm’s price-to-earnings (P/E) ratio remains unusually high, sitting between 61 and 66—far above the healthcare sector average of 21.9 and competitors’ average of 28.4.

CEO Andrew Dudum defended the buyback, calling it a strong signal of belief in the company’s future. Yet investors have continued to sell, pushing the stock lower despite leadership’s efforts.

The $250 million buyback program will run until 2028, but its impact remains uncertain. Shares have kept falling, and the CFO’s recent sale has added to doubts about recovery. With a P/E ratio well above industry norms, analysts will be watching closely to see if the company can justify its valuation.

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