[144] Lemonade, Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Lemonade, Inc. (LMND) notifying a proposed sale of common stock and disclosure of recent related transactions.

• Proposed sale: 5,000 common shares via Oppenheimer & Co.; aggregate market value $239,650; approximate sale date 08/05/2025; exchange: NYSE.
• Outstanding shares: 73,886,417.
• Acquisition details: 1,250 shares acquired 12/24/2019 (Employee Stock Option Plan); 3,750 shares acquired 06/07/2020 (Employee Stock Option Plan).
• Recent sale (past 3 months): Adina Eckstein sold 5,000 shares on 06/23/2025 for gross proceeds $225,000.

The filer represents no undisclosed material adverse information and includes standard signature/attestation language required by Form 144.

Insights

Financial Analyst

TL;DR: Small insider disposal disclosed: 5,000 shares proposed for sale, immaterial relative to total outstanding shares.

The filing reports a proposed sale of 5,000 common shares (agg. market value $239,650) scheduled 08/05/2025 and a recent sale of 5,000 shares on 06/23/2025 for $225,000. Acquisition dates and sources are employee stock option plan grants dated 12/24/2019 and 06/07/2020. Given the issuer's stated outstanding share count of 73,886,417, the reported amounts represent a negligible percentage of outstanding stock. No earnings, guidance, or other financial metrics are provided in this filing.

Corporate Governance Expert

TL;DR: Routine Rule 144 notice and post-sale disclosure; filings follow required attestations and include transaction provenance.

The Form 144 discloses transaction provenance (employee stock option plan) and includes the required attestation that the seller has no undisclosed material information. It also records broker details (Oppenheimer & Co.) and exchange (NYSE). The filing contains no indication of a 10b5-1 plan adoption date. From a governance perspective, disclosures appear to meet Form 144 content requirements but do not by themselves imply firm-level governance change.

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	Oppenheimer & Co. Inc. 85 Broad St. New York NY 10004	5000	239650.00	73886417	08/05/2025	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	12/24/2019	Employee Stock Option plan	Issuer			1250	08/05/2025	Cash - Upon execution
Common	06/07/2020	Employee Stock Option plan	Issuer			3750	08/05/2025	Cash - Upon execution

* 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
Eckstein Adina 5 CROSBY STREET 3RD FLOOR NEW YORK NY 10013	Common	06/23/2025	5000	225000.00

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 LMND Form 144 report?

The filing reports a proposed sale of 5,000 common shares via Oppenheimer with an aggregate market value of $239,650 and a proposed sale date of 08/05/2025.

Who sold shares in the past three months for LMND?

Adina Eckstein sold 5,000 common shares on 06/23/2025 for gross proceeds of $225,000.

How were the shares to be sold acquired?

The securities to be sold were acquired under the Employee Stock Option Plan: 1,250 shares on 12/24/2019 and 3,750 shares on 06/07/2020.

What is the issuer's outstanding share count reported in the filing?

The filing lists 73,886,417 shares outstanding.

Which broker and exchange are named in the Form 144?

Broker: Oppenheimer & Co. Inc., 85 Broad St. New York NY 10004. Exchange: NYSE.