LMND Form 144: Option-derived sale via Fidelity for 38,155 shares

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) filed a Form 144 disclosing a proposed sale of 38,155 shares of common stock through Fidelity Brokerage Services LLC (900 Salem Street, Smithfield, RI) on the NYSE with an aggregate market value of $2,289,300.00. The company shows 73,886,417 shares outstanding, so the proposed sale equals about 0.052% of outstanding shares.

The securities are reported as acquired under an option granted 02/06/2019, with the acquisition and planned sale dated 08/13/2025, and payment noted as cash. The filing also lists two prior sales by John Peters in the past three months: 1,494 shares on 06/03/2025 for $52,664.98 and 6,543 shares on 06/23/2025 for $294,435.00. Other filer and notice administrative fields are not populated in the provided content.

Insights

Securities Analyst

TL;DR: A small, disclosed option-derived sale of 38,155 LMND shares (~$2.29M)—unlikely to move the market on its own.

The Form 144 reports a proposed sale of 38,155 common shares through Fidelity with an aggregate value of $2,289,300, representing roughly 0.052% of the 73,886,417 shares outstanding reported in the filing. The securities are tied to an option granted 02/06/2019 and are recorded as acquired and to be sold on 08/13/2025. Two recent smaller sales by the named individual are disclosed for June 2025, indicating prior disposition activity. Based solely on disclosed amounts, this is a routine insider sale with limited market impact.

Corporate Governance Expert

TL;DR: The filing documents compliance with disclosure requirements for an option-derived sale; details on the filer are incomplete in the provided content.

The notice identifies the broker, class of security, acquisition method (option granted in 2019), and transaction economics including aggregate market value and outstanding share count. Prior sales by John Peters in June 2025 are itemized with proceeds, supporting transparency about recent dispositions. The filing excerpt does not populate some administrative fields such as the filer CIK or signature/date fields in the provided content, so completeness of the public filing cannot be fully assessed from this excerpt alone.

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	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	38155	2289300.00	73886417	08/13/2025	NYSE

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	08/13/2025	Option Granted - 02/06/2019	Issuer			38155	08/13/2025	Cash

* 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
John Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2025	1494	52664.98
John Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/23/2025	6543	294435.00

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 Lemonade (LMND) report in this Form 144?

The filing discloses a proposed sale of 38,155 common shares via Fidelity Brokerage Services LLC on the NYSE with aggregate market value of $2,289,300.00.

When is the approximate sale date and how were the shares acquired?

The filing lists an approximate sale date of 08/13/2025 and indicates the shares were acquired under an option granted 02/06/2019, with payment noted as cash.

How large is the proposed sale relative to outstanding shares for LMND?

The filing reports 73,886,417 shares outstanding; the proposed sale of 38,155 shares is about 0.052% of that total.

Has the seller disposed of LMND shares recently?

Yes. The filing lists two sales by John Peters: 1,494 shares on 06/03/2025 for $52,664.98 and 6,543 shares on 06/23/2025 for $294,435.00.

Who is the broker handling the proposed sale?

The broker named in the filing is Fidelity Brokerage Services LLC (900 Salem Street, Smithfield, RI 02917).