Form 4: Upstart CTO Paul Gu Plans 100K Share Buy, Remits Short-Swing Profit

Upstart Holdings, Inc. CTO and Director Paul Gu plans to acquire 100,000 shares of common stock on November 11, 2025, and has remitted $148,255.06 in short-swing profits to the company.

Summary

• Paul Gu, Chief Technology Officer and Director of Upstart Holdings, Inc. (UPST), plans to acquire a total of 100,000 shares of common stock on November 11, 2025, pursuant to a Rule 10b5-1 plan.
• 20,000 shares will be purchased at a weighted average price of $39.22 per share (ranging from $38.89 to $39.39) by THE GU QIAO FAMILY TRUST, of which Mr. Gu is the trustee.
• 80,000 shares will be purchased at a weighted average price of $39.23 per share (ranging from $38.93 to $39.40) by JECCO, LLC, of which Mr. Gu is a managing member.
• Following these planned transactions, Paul Gu's beneficial ownership will include 20,000 shares by THE GU QIAO FAMILY TRUST, 80,000 shares by JECCO, LLC, 1,102,226 shares directly (including Restricted Stock Units), and 44,930 shares by THE PAUL XINQUAN GU 2021 GIFTING TRUST.
• These planned purchases are matchable under Section 16(b) of the Securities Exchange Act of 1934 with a prior sale of 5,000 shares by Mr. Gu on September 2, 2025.
• Paul Gu has already remitted $148,255.06 in short-swing profits to Upstart Holdings, Inc. due to this matchable transaction.

Sentiment

Score: 6

Explanation: The significant planned insider purchase is a strong positive signal of confidence, but it is somewhat offset by the negative implication of a past Section 16(b) violation and the required profit remittance, which points to a compliance oversight.

Positives

• A significant planned insider purchase of 100,000 shares by the Chief Technology Officer and Director, Paul Gu, indicates confidence in the company's future prospects.
• The average planned purchase prices of $39.22 and $39.23 per share suggest a belief that the stock is undervalued at these levels.
• The prompt remittance of short-swing profits demonstrates compliance with Section 16(b) regulations, rectifying the financial impact of the violation for the company.

Negatives

• The reporting person, Paul Gu, was involved in a transaction that triggered a Section 16(b) short-swing profit violation, requiring the remittance of $148,255.06 to the company, indicating a past lapse in compliance or oversight regarding insider trading rules.

Risks

• The occurrence of a Section 16(b) short-swing profit violation by a senior officer and director, even if rectified, could raise questions about internal compliance procedures and oversight regarding insider trading policies.

Future Outlook

The filing does not contain any explicit forward-looking statements or guidance regarding the company's future performance or strategic direction, beyond the planned stock acquisition.

Industry Context

This planned insider buying activity, despite the Section 16(b) issue, could be interpreted by the market as a positive signal of confidence from a key executive in the company's future, which is particularly relevant in the often volatile FinTech and AI lending sectors where Upstart operates. The use of a Rule 10b5-1 plan indicates a pre-arranged, structured approach to stock acquisition.

Corporate Governance

Legal Proceedings

• The reporting person was subject to Section 16(b) of the Securities Exchange Act of 1934, which resulted in the remittance of $148,255.06 in short-swing profits to the company. This is a regulatory compliance matter that has been resolved through remittance.

Related Party Transactions

• The planned acquisitions will be made indirectly through THE GU QIAO FAMILY TRUST and JECCO, LLC, both of which are entities where the Reporting Person, Paul Gu, holds a controlling or trustee role, making them related party transactions.
• Existing beneficial ownership also includes shares held by THE PAUL XINQUAN GU 2021 GIFTING TRUST, where the Reporting Person is a trustee.

Stakeholder Impact

• Shareholders: The planned insider purchase could be seen as a positive signal of management confidence, potentially boosting investor sentiment. The remittance of short-swing profits benefits the company (and thus shareholders) financially.
• Regulatory Authorities: The Section 16(b) violation and subsequent remittance demonstrate the enforcement of insider trading rules, reinforcing regulatory oversight.

Next Steps

• The Reporting Person undertakes to provide full information regarding the number of shares purchased at each separate price to the Issuer, any security holder, or the SEC staff upon request.

Key Dates

Recommendation

While the significant planned insider buying by the CTO signals strong confidence in Upstart's future, which is a positive indicator, the simultaneous Section 16(b) violation and required profit remittance introduce a notable corporate governance concern. This mixed signal suggests a 'hold' position, as the positive sentiment from insider buying is tempered by the compliance issue, warranting further observation of the company's operational performance and governance practices.

Keywords

Upstart Holdings, UPST, Paul Gu, Insider Trading, Form 4, Stock Purchase, Chief Technology Officer, Director, Section 16(b), Short-Swing Profit, Equity Acquisition, Corporate Governance, Rule 10b5-1