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.

CTO Gu Paul purchased 100,000 shares of UPST for $3,922,800.00 at $39.23 avg; stock down 58.0% from 52-week high.

Gu Paul, Chief Technology Officer, executed 2 separate purchases totaling 100,000 shares for $3,922,800.00 on 2025-11-11, at an average price of $39.23, bringing his holdings to 80,000 shares post-transaction. This purchase occurs while UPST trades $37.29, down 58.0% from its 52-week high of $88.77 and down 26.0% over the past 30 days. Notably, Gu's prior trading history at UPST shows 5 consecutive well-timed sales—all 5 prior trades captured subsequent declines with 90-day returns ranging from -14.6% to -44.8%—suggesting demonstrated market timing skill specific to this ticker. However, the company currently faces structural headwinds: though it posted $277.1M in quarterly revenue (+23.9% annual growth) and returned to profitability with $31.8M net income last quarter, it was unprofitable over the most recent full fiscal year, and the stock's 41.8% 90-day decline reflects sustained investor skepticism despite the turnaround. The insider's willingness to deploy $3.9M near a multi-year low, combined with his track record of well-timed exits at this ticker, suggests conviction in a recovery at current levels, though the magnitude of recent losses and full-year unprofitability warrant careful evaluation of whether the downturn has fully priced in operational risks.

CEO Dave Girouard sold 41.7K shares ($2.7M) at $64.93; retains 52.6K shares. Substantial reduction in stake.

CEO Dave Girouard executed two separate sales on 2025-09-15, totaling 41.7K shares for $2.7M at a blended average price of $64.93—a discount of approximately 4.7% to the current price of $68.12. This transaction reduces his stake by 44.2% from 94.3K shares to 52.6K shares post-transaction. Girouard's recent trading history at UPST shows mixed results: of his 5 prior trades at this ticker, four were sells that experienced 30-day declines ranging from -0.2% to -15.5%, while one sell on 2025-06-20 saw a +30.5% 30-day return. His cross-ticker track record shows 19 prior sells with an avg 90-day return of -19.5% and a well-timed rate of 71.43%, but crucially, none of his UPST-specific 90-day outcomes have yet materialized. The company remains unprofitable on a full-year basis despite $257.3M in recent quarterly revenue and +23.9% annual growth, which underscores uncertainty about near-term profitability trajectory. The sale at a discount to current levels, combined with the substantial reduction in personal stake at a time when the stock has recovered +15.3% over 90 days, warrants investor attention to whether this reflects CEO positioning ahead of potential headwinds.

CEO Dave Girouard sells 41,667 shares at $63.27 avg for $2.6M via scheduled 10b5-1 plan; retains 52.6K shares.

Dave Girouard, Chief Executive Officer of Upstart Holdings, filed a Form 4 reporting two separate sales totaling 41,667 shares for $2,636,433.56 on 2025-08-15, executed at an average blended price of $63.27. This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2024-08-29, meaning the sales were scheduled in advance rather than discretionary decisions. Post-transaction, Girouard retains 52,614 shares, representing a reduction of 44.2% from his pre-transaction holdings of 94,281 shares. Since the sales are governed by a pre-established trading plan, they reflect a planned portfolio structure rather than a real-time market signal or conviction-based decision on current valuations.

CEO Girouard sells 41,667 shares for $3.1M under 10b5-1 plan adopted 2024-08-29

Dave Girouard, Chief Executive Officer, executed 2 separate sales totaling 41,667 shares for $3,127,831.38 at a blended average price of $75.07 on 2025-07-15. The transaction was conducted under a pre-arranged 10b5-1 trading plan adopted on 2024-08-29, meaning this is a scheduled, non-discretionary trade rather than a discretionary decision made at the time of execution. Post-sale holdings fell to 52,614 shares, representing a reduction of 44.2% from pre-transaction holdings of 94,281 shares. Since this transaction is governed by a pre-determined plan, the timing and execution reflect the mechanics of the plan rather than any judgment call by the CEO.

CEO Dave Girouard sold 41,667 shares of UPST at $60.05 (total: $2,501,982.52) via pre-arranged 10b5-1 plan; holdings drop to 52,614 shares (-44.2%).

CEO Dave Girouard executed a scheduled sale of 41,667 shares under a pre-arranged 10b5-1 trading plan adopted on 2024-08-29, reducing his stake by 44.2% from 94,281 to 52,614 shares. The transaction was non-discretionary, so no timing inference should be drawn; 10b5-1 plans operate on predetermined schedules independent of market conditions or conviction. The substantial reduction in personal shareholding—halving his direct equity stake—is notable for capital markets observers, as it represents a material reduction in CEO-level ownership exposure to the company.

UPST CEO Girouard sells 41,667 shares for $2.5M under 10b5-1 plan; holdings drop to 52,614

Girouard Dave, Chief Executive Officer of Upstart Holdings, sold 41,667 shares at $60.11 on 2025-06-11, reducing his stake by 44.2% from 94,281 to 52,614 shares. This transaction was executed under a pre-arranged 10b5-1 trading plan adopted on 2024-08-29, meaning it was scheduled rather than discretionary and therefore does not reflect real-time market judgment or sentiment. The substantial reduction in CEO holdings — removing nearly half his position — is notable from a governance perspective, though the plan-based execution prevents attribution to any specific market view or timing decision by the executive.

Chief Legal Officer Darling Scott sells 17,507 shares for $1,145,543.59 under pre-arranged 10b5-1 plan

Darling Scott, Chief Legal Officer of Upstart Holdings, executed 4 separate sales totaling 17,507 shares for $1,145,543.59 on February 28 and March 3, 2025, at a blended average price of $65.43. The sales were conducted under a pre-arranged 10b5-1 trading plan adopted on 2024-11-27, meaning this transaction was scheduled and not discretionary. Post-transaction holdings stand at 150,129 shares, representing a 10.4% reduction from pre-transaction holdings of 167,636 shares. Since this activity is governed by a prearranged plan, it does not reflect timing-based judgment or signaling of near-term conviction regarding company prospects.

CEO Girouard sells 41,667 shares for $3.5M under pre-arranged 10b5-1 plan adopted 2024-08-29

Girouard Dave, CEO of Upstart Holdings, executed 3 separate sales totaling 41,667 shares for $3,526,908.23 on 2025-02-18, reducing his holdings from 98,805 shares to 57,138 shares (a 42.2% reduction). This transaction was conducted under a pre-arranged 10b5-1 trading plan adopted on 2024-08-29, meaning it was scheduled and not discretionary. The blended average sale price was $84.65 across the three transactions. As a scheduled disposition under a pre-existing plan, this filing reflects contractual execution rather than a market-timing decision by the CEO.