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  4. [Form 4] Upstart Holdings, Inc. Insider Trading Activity

Upstart (NASDAQ: UPST) CLO holds 87,186 shares after tax sale

Filing Impact
(Neutral)
Filing Sentiment
(Negative)
Form Type
4

Rhea-AI Filing Summary

Upstart Holdings, Inc. (UPST) reported that Chief Legal Officer Scott Darling sold 814 shares of common stock on August 17, 2026 at a weighted average price of $29.3588. The sale was made to cover tax withholding obligations arising from vesting restricted stock units (RSUs). After this sale, Darling held 87,186 shares directly, including RSUs, and 40,426 shares indirectly through the Darling Family Trust, which recently received a deposit of 728 shares.

Positive

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Negative

  • None.
Insider Darling Scott
Role Chief Legal Officer
Sold 814 shs ($24K)
Type Security Shares Price Value
Sale Common Stock F1, F2, F3 814 $29.3588 $24K
holding Common Stock F4, F5 -- -- --
Holdings After Transaction: Common Stock — 87,186 shares (Direct); Common Stock — 40,426 shares (Indirect, See Footnote)
Footnotes (5)
  1. F1. These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs).
  2. F2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.19 to $29.53. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price.
  3. F3. Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Common Stock, subject to the applicable vesting schedule and conditions of each RSU.
  4. F4. The shares are held by the Darling Family Trust.
  5. F5. The number of shares held reflects the deposit of 728 shares of Common Stock from the Reporting Person to the Darling Family Trust.
Shares sold 814 shares Common stock sale on August 17, 2026 to cover tax withholding
Weighted average sale price $29.3588 per share Sale of 814 common shares in multiple transactions between $29.19 and $29.53
Direct holdings after transaction 87,186 shares Common stock directly held by Scott Darling after the August 17, 2026 sale
Indirect holdings after transaction 40,426 shares Common stock held by the Darling Family Trust after a deposit of 728 shares
Deposit to trust 728 shares Number of UPST shares deposited by Scott Darling into the Darling Family Trust
Net buy/sell shares -814 shares Net effect of reported insider transactions in this filing
restricted stock units (RSUs) financial
"Certain of these securities are RSUs. Each RSU represents a contingent right"
Restricted stock units (RSUs) are a type of company promise to give employees shares of stock in the future, usually after certain conditions like working for a set time. They are like a gift promised today that you receive later, which can become valuable if the company's stock price goes up. RSUs matter because they are a way companies reward employees and can be a significant part of compensation.
weighted average price financial
"The price reported in Column 4 is a weighted average price."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
tax withholding obligations financial
"These shares were sold to cover tax withholding obligations in connection"
indirect financial
"The shares are held by the Darling Family Trust."

FAQ

At what price were the 814 UPST shares sold by Scott Darling?
The 814 shares were sold at a weighted average price of $29.3588 per share. Footnotes state the trades occurred in multiple transactions, with prices ranging from $29.19 to $29.53 across the executed sales.

How many UPST shares does Scott Darling hold directly after this transaction?
Following the sale, Scott Darling directly holds 87,186 UPST shares. Footnotes clarify that certain of these securities are RSUs, each representing a contingent right to receive one share of common stock subject to vesting conditions.

What is Scott Darling’s indirect ownership in UPST after the reported Form 4?
Indirectly, Scott Darling is associated with 40,426 UPST shares held by the Darling Family Trustdeposit of 728 shares of common stock from Darling to the trust, as described in the footnotes.

Was Scott Darling’s UPST stock sale part of a Rule 10b5-1 trading plan?
The filing’s Rule 10b5-1 checkbox is not marked as affirmative, and no footnote states the sale was under such a plan. The sale is described instead as covering tax withholding obligations related to RSU vesting.

Why did Scott Darling sell UPST shares instead of paying taxes in cash?
The Form 4 notes the shares were sold to cover tax withholding obligations from RSU vesting. This indicates shares were used to satisfy required withholding taxes, a common administrative approach for equity compensation events.

What do the RSUs mentioned in Scott Darling’s UPST Form 4 represent?
Footnotes state that certain holdings are restricted stock units (RSUs), each representing a contingent right to receive one UPST share. These RSUs are subject to an applicable vesting schedule and other conditions before shares are delivered.

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Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Darling Scott
(Last)(First)(Middle)
C/O UPSTART HOLDINGS, INC.
220 PARK ROAD, SUITE 500
(Street)
BURLINGAME CALIFORNIA 94010
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Upstart Holdings, Inc. [ UPST ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Legal Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
08/17/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock08/17/2026S(1)814D$29.3588(2)87,186(3)D
Common Stock40,426ISee Footnote(4)(5)
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
1. These shares were sold to cover tax withholding obligations in connection with the vesting of restricted stock units (RSUs).
2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.19 to $29.53. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price.
3. Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of Common Stock, subject to the applicable vesting schedule and conditions of each RSU.
4. The shares are held by the Darling Family Trust.
5. The number of shares held reflects the deposit of 728 shares of Common Stock from the Reporting Person to the Darling Family Trust.
Remarks:
/s/ Steven Madrid, by power of attorney08/19/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR