Upstart officer plans $3.17M stock sale

Rhea-AI Filing Summary

Upstart Holdings, Inc. (UPST) received a notice under Rule 144 that officer Sanjay Datta intends to sell 116,000 shares of common stock through Charles Schwab & Co., Inc., with an indicated aggregate market value of $3,166,196, in connection with an employee stock option cashless exercise dated September 8, 2026.

The notice also lists prior sales of Upstart common stock by Sanjay Datta over the past three months, including transactions on June 9, 2026, August 17, 2026, August 19, 2026, and August 20, 2026.

Key Figures

Shares to be sold: 116,000 shares Aggregate market value: $3,166,196 Sale on June 9, 2026: 15,000 shares; $456,116 +3 more

6 metrics

Shares to be sold 116,000 shares Common stock covered by the Rule 144 notice for planned sale

Aggregate market value $3,166,196 Indicated value of 116,000 shares in the planned Rule 144 sale

Sale on June 9, 2026 15,000 shares; $456,116 Common stock sold by Sanjay Datta during the past three months

Sale on August 17, 2026 2,033 shares; $59,683 Common stock sold by Sanjay Datta during the past three months

Sale on August 19, 2026 10,000 shares; $314,633 Common stock sold by Sanjay Datta during the past three months

Sale on August 20, 2026 8,945 shares; $251,298 Common stock sold by Sanjay Datta during the past three months

Key Terms

Rule 144, Employee Stock Option Exercise, cashless exercise, aggregate market value

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Employee Stock Option Exercise financial

"Common | 09/08/2026 | Employee Stock Option Exercise | Upstart Holdings, Inc."

cashless exercise financial

"116000 | 09/08/2026 | Broker Payment for Cashless Exercise"

A cashless exercise is a way for an option holder to convert stock options into actual shares without paying the purchase price in cash; instead they immediately give up a portion of the newly issued shares to cover the cost and any withholding taxes. Investors care because this process increases the number of shares available and can slightly dilute existing holdings, while also signaling how insiders or employees are realizing compensation without needing cash — similar to paying for a purchase by handing over part of what you just bought.

aggregate market value financial

"Common ... 116000 | 3166196.00 | ... | 09/08/2026"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

FAQ

What does the Form 144 filing disclose for Upstart Holdings, Inc. (UPST)?

It discloses that officer Sanjay Datta filed a Rule 144 notice to sell 116,000 shares of Upstart common stock, with an indicated aggregate market value of $3,166,196, in connection with an employee stock option cashless exercise dated September 8, 2026.

How many UPST shares are covered by the new Rule 144 notice?

The notice covers 116,000 shares of Upstart Holdings, Inc. common stock. These shares are to be sold through Charles Schwab & Co., Inc. and relate to an employee stock option cashless exercise dated September 8, 2026.

What is the aggregate market value of the UPST shares in the planned Rule 144 sale?

The filing states an aggregate market value of $3,166,196 for the 116,000 shares of Upstart common stock that officer Sanjay Datta intends to sell under Rule 144 through Charles Schwab & Co., Inc.

What recent UPST share sales by Sanjay Datta are listed in the past three months?

The notice lists sales of Upstart common stock by Sanjay Datta on June 9, 2026 (15,000 shares for $456,116), August 17, 2026 (2,033 shares for $59,683), August 19, 2026 (10,000 shares for $314,633), and August 20, 2026 (8,945 shares for $251,298).

On which market are the UPST shares in this Form 144 filing listed?

The shares referenced in the notice are Upstart Holdings, Inc. common stock listed on NASDAQ. The planned Rule 144 sale involves 116,000 shares associated with an employee stock option cashless exercise on September 8, 2026.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/08/2026 - 05:09 PM Accepted by SEC EDGAR 09/08/2026 - 05:09 PM Learn about SEC filing dates

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	0001832808
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Upstart Holdings, Inc.
SEC File Number	001-39797
Address of Issuer	220 PARK ROAD SUITE 500 BURLINGAME CALIFORNIA 94010
Phone	(650) 204-1000
Name of Person for Whose Account the Securities are To Be Sold	Datta Sanjay
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	Officer

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	116000	3166196.00	97313046	09/08/2026	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	09/08/2026	Employee Stock Option Exercise	Upstart Holdings, Inc.			116000	09/08/2026	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
SANJAY DATTA 220 Park Road, Suite 500 Burlingame CA 94010	Upstart Holdings, Inc.	06/09/2026	15000	456116.00
SANJAY DATTA 220 Park Road, Suite 500 Burlingame CA 94010	Upstart Holdings, Inc.	08/17/2026	2033	59683.00
SANJAY DATTA 220 Park Road, Suite 500 Burlingame CA 94010	Upstart Holdings, Inc.	08/19/2026	10000	314633.00
SANJAY DATTA 220 Park Road, Suite 500 Burlingame CA 94010	Upstart Holdings, Inc.	08/20/2026	8945	251298.00

144: Remarks and Signature

Remarks
Date of Notice	09/08/2026
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	SANJAY DATTA
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)