[144] Upstart Holdings, Inc. SEC Filing

Rhea-AI Filing Summary

Upstart Holdings insider Scott Darling notified the SEC of a proposed sale under Rule 144 for 1,000 common shares to be sold through Charles Schwab on 10/01/2025 on NASDAQ with an aggregate market value of $54,640. The shares were acquired and are being disposed of on 10/01/2025 via an employee stock option exercise and a cashless broker payment. The filing lists multiple prior insider sales by Scott Darling between 07/01/2025 and 09/17/2025, including transactions of 2,000; 5,000; 5,000; 4,000; 6,853; 6,402; 4,000; and 1,000 shares with corresponding gross proceeds shown for each sale.

Positive

• Required Rule 144 disclosure filed, indicating procedural compliance for the proposed sale
• Brokered transaction via Charles Schwab, showing use of standard brokerage channels for the sale

Negative

• Repeated insider sales by Scott Darling between 07/01/2025 and 09/17/2025 (multiple transactions listed)
• Insider monetization following option exercises could be viewed as reduced insider shareholdings (transactions and gross proceeds are disclosed)

Insights

Securities Analyst

TL;DR: Insider filing shows routine disposition following option exercise; prior sales indicate ongoing monetization.

The Form 144 documents a planned sale of 1,000 Upstart common shares on 10/01/2025 via Charles Schwab after an employee option exercise and cashless exercise payment that same day. The filing also discloses a series of prior sales by Scott Darling from July through September 2025, with individual gross proceeds listed. From a market-impact perspective, this is a disclosure of insider liquidity activity rather than new corporate developments; the filing confirms the use of proper broker channels and compliance with Rule 144 reporting requirements.

Corporate Governance Expert

TL;DR: Form 144 is a compliance disclosure showing insider sales; pattern may be relevant to governance monitoring.

The notice indicates the insider represented no undisclosed material adverse information at signature. The planned sale stems from an employee stock option exercise executed and sold on the same date via a cashless broker payment. Multiple prior sales by the same individual are detailed with dates and proceeds, which is useful for monitoring insider trading patterns and assessing alignment of insider actions with governance policies. No statements about material company events are made in the filing.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Charles Schwab & Co., Inc. 3000 Schwab Way Westlake TX 76262	1000	54640.00	96217742	10/01/2025	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	10/01/2025	Employee Stock Option Exercise	Upstart Holdings, Inc.			1000	10/01/2025	Broker Payment for Cashless Exercise

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc.	07/01/2025	2000	127120.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc.	07/02/2025	5000	350176.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc	07/08/2025	5000	400210.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc	08/01/2025	4000	313807.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc	08/20/2025	6853	419159.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc	08/25/2025	6402	435336.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc	09/03/2025	4000	277654.00
SCOTT DARLING 950 S. DELAWARE STREET, SUITE 410 SAN MATEO CA 94403	Upstart Holdings, Inc	09/17/2025	1000	70010.00

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What securities does the Form 144 for UPST report?

The filing reports a proposed sale of 1,000 shares of Upstart Holdings, Inc. common stock.

When and where is the proposed sale scheduled?

The sale is scheduled for 10/01/2025 on NASDAQ through Charles Schwab & Co., Inc.

How were the 1,000 shares acquired by the filer?

The shares were acquired on 10/01/2025 via an employee stock option exercise and paid through a broker cashless exercise.

Has the filer sold other Upstart shares recently?

Yes. The filing lists prior sales by Scott Darling between 07/01/2025 and 09/17/2025 with individual amounts and gross proceeds shown for each transaction.

What was the aggregate market value reported for the proposed 1,000-share sale?

The aggregate market value reported for the 1,000 shares is $54,640.00.