UPST Upstart Holdings, Inc. Insider Trading

CEO Paul Gu buys 50,000 shares at $27.50 on weakness; third open-market purchase in three years after 64 prior sales.

Paul Gu, the Chief Executive Officer of Upstart Holdings, deployed $1.375 million to purchase 50,000 shares, representing his third open-market purchase in roughly three years—a striking reversal from his dominant pattern of 64 prior sales over the same period. The stock is trading nearly 70% below its 52-week high and has declined over the prior three-month period, yet Gu is buying. His last two open-market purchases at Upstart, made simultaneously at the same price on the same date, were both followed by strong near-term gains before giving back those returns over a longer horizon. This current purchase carries similar mixed-signal historical weight: Gu's prior buys at this company posted gains within 30 days but roughly flat returns at the 90-day mark, while his prior sells at Upst were all well-timed, with the stock declining after each exit. Upstart itself remains profitable with strong annual revenue growth, though the most recent quarter showed a net loss, creating a contrast between the macro growth story and near-term earnings weakness that mirrors the conflicting signals in Gu's own historical timing at the stock. The rare CEO purchase into a temporary downturn deserves attention, but his track record at this company shows conflicting timing outcomes—earlier buys rebounded quickly but stalled longer term, while his sells proved consistently prescient.

Director Dave Girouard purchases 170,240 shares at ~$29, marking first open-market buy after 31 prior sales.

Dave Girouard, a director and 10% owner of Upstart, is switching from net seller to net buyer for the first time, acquiring over 170,000 shares in open-market purchases. This represents a significant departure from his prior activity: over three years he had sold shares repeatedly but never bought on the open market. The timing is notable—the stock is trading well below its annual highs, down sharply over the past quarter. Girouard's five prior sales in Upstart stock all proved well-timed: the stock fell after every exit, validating his past exits over both near and long-term horizons. By reversing course to buy at these lower prices, he is re-engaging with the company despite ongoing quarterly losses, even as the company maintains annual profitability and is growing revenue at a double-digit rate. The shift from repeated sales to a large open-market purchase breaks a consistent three-year pattern and warrants close attention to whether his prior sales marked a bottom or whether this buy represents a contrarian move in a still-declining stock.