[144] Upstart Holdings, Inc. SEC Filing

Rhea-AI Filing Summary

Upstart Holdings, Inc. (UPST) Form 144 notice: The filing notifies a proposed sale of 1,000 common shares via Charles Schwab on 09/17/2025 with an aggregate market value of $70,010. The shares were acquired on the same date through an employee stock option exercise and appear to be part of a cashless exercise settled through the broker.

The filer also discloses prior dispositions by the same person, Scott Darling, totaling 33,255 shares sold across seven transactions from 07/01/2025 to 09/03/2025 with aggregate gross proceeds of approximately $2,323,462. The filing states the seller represents no undisclosed material adverse information.

Positive

• Disclosure compliance met: the filer provides required details about acquisition method, broker, and intended sale date
• Use of cashless exercise indicates the sale proceeds were used to satisfy option exercise cost rather than requiring external financing

Negative

• Insider selling activity: the filer (Scott Darling) sold 33,255 shares in seven transactions from 07/01/2025 to 09/03/2025
• Aggregate proceeds from those sales are approximately $2,323,462, which may attract investor attention despite being a small fraction of outstanding shares

Insights

Securities Analyst

TL;DR: Routine insider disposition following option exercise; amount represents modest percentage of outstanding shares.

The filing documents a proposed sale of 1,000 shares acquired via an employee stock option exercise and settled cashlessly, which is a common mechanism for insiders to realize gains from equity compensation without an outlay of cash. The disclosed prior sales by the same individual total 33,255 shares and roughly $2.32 million in proceeds over two months. Relative to the reported outstanding share count of 96,217,742, these transactions are small in percentage terms but are material from an insider-activity disclosure perspective. No claims in the filing suggest undisclosed operational issues; this is a compliance disclosure of insider selling.

Corporate Governance Expert

TL;DR: Compliance-focused filing showing option exercise and subsequent market sales; standard certification included.

The Form 144 correctly reports the nature of acquisition (employee stock option exercise), the broker, intended sale date, and historical sales by the same person. The signer affirms absence of material nonpublic information and the form reiterates statutory warnings about misstatements. From a governance standpoint this is a routine transparency filing required when certain conditions for restricted securities sales are met; it contains no governance red flags beyond concentrated insider selling activity disclosed in the past three months.

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	70010.00	96217742	09/17/2025	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	09/17/2025	Employee Stock Option Exercise	Upstart Holdings, Inc.			1000	09/17/2025	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

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 does the UPST Form 144 filed on 09/17/2025 report?

The form reports a proposed sale of 1,000 common sharesemployee stock option exercise and intended to be sold through Charles Schwab on 09/17/2025 with an aggregate market value of $70,010.

Who has recently sold Upstart (UPST) shares according to this filing?

Scott Darling is listed as the seller for multiple transactions totaling 33,255 shares sold between 07/01/2025 and 09/03/2025.

How much did the prior sales by Scott Darling generate?

The seven disclosed sales generated aggregate gross proceeds of approximately $2,323,462.

How were the 1,000 shares being sold on 09/17/2025 acquired?

They were acquired on 09/17/2025 through an employee stock option exercise and the payment method is noted as a broker payment for a cashless exercise.

Does the filing indicate any undisclosed material information about Upstart?

The filer represents by signature that they do not know any material adverse information about the issuer that has not been publicly disclosed.