[144] Lemonade, Inc. SEC Filing

Rhea-AI Filing Summary

Lemonade insider Adina Eckstein filed a Form 144 notifying a proposed sale of 5,000 common shares to be executed through Oppenheimer & Co. on 08/11/2025 with an aggregate market value of $244,900. The shares were acquired on 06/07/2020 under an employee stock option plan and will be paid in cash upon exercise. The filing lists 73,886,417 shares outstanding, making the proposed block about 0.0068% of outstanding stock. The filer disclosed two recent sales in the past three months totaling 10,000 shares for $470,000 in gross proceeds. The notice includes the standard representation that the filer is not aware of any undisclosed material adverse information.

Positive

• Rule 144 disclosure filed, providing regulatory transparency about proposed insider selling
• Securities were acquired under an employee stock option plan, clarifying the origin of the shares
• Prior sales and gross proceeds are disclosed (10,000 shares, $470,000), improving transaction traceability

Negative

• Multiple recent sales by the same person in the past three months (total 10,000 shares) which may prompt investor questions
• No date provided for a 10b5-1 trading plan in the filing, leaving uncertainty whether sales are preplanned

Insights

Securities Analyst

TL;DR: Small, routine insider sale; disclosed under Rule 144 with limited market impact given the tiny percentage of outstanding shares.

The filing shows a proposed sale of 5,000 shares valued at $244,900 and prior sales of 10,000 shares in the past three months for $470,000. Relative to the reported 73,886,417 shares outstanding, these transactions represent an immaterial percentage (~0.0068% for the proposed sale), suggesting limited direct valuation impact. The shares were acquired via an employee stock option plan, indicating this is an exercise/liquidity event rather than a transfer from external holdings. Documentation appears complete for a Rule 144 notice.

Corporate Governance Expert

TL;DR: Multiple recent insider sales are disclosed but are small in absolute and relative terms; governance disclosure requirements appear satisfied.

The filer disclosed two prior sales and the current proposed sale, all reported with dates and gross proceeds, which supports transparency. The filing does not show a stated Rule 10b5-1 plan adoption date, so it is unclear whether sales are preplanned; the form does include the standard representation about lack of material nonpublic information. From a governance perspective, continued disclosure is appropriate; the overall size of sales reduces immediate material concern for shareholders.

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	244900.00	73886417	08/11/2025	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	06/07/2020	Employee Stock Option Plan	Issuer			5000	08/11/2025	Cash - Upon 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
Eckstein Adina 5 CROSBY STREET New York NY 10013	Common	06/23/2025	5000	225000.00
Eckstein Adina 5 CROSBY STREET New York NY 10013	Common	08/05/2025	5000	245000.00

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 did Lemonade (LMND) disclose in this Form 144?

The filing notifies a proposed sale of 5,000 common shares to be sold via Oppenheimer on 08/11/2025 with an aggregate market value of $244,900.

Who is the filer named on the Form 144 for LMND?

The filer is listed as Adina Eckstein with an address in New York as shown in the notice.

How were the shares being sold acquired?

The 5,000 shares were acquired on 06/07/2020 under an Employee Stock Option Plan and payment will be cash upon exercise.

Has the filer sold other Lemonade shares recently?

Yes. The filing discloses two sales in the past three months: 5,000 shares on 06/23/2025 for $225,000 and 5,000 shares on 08/05/2025 for $245,000.

What percentage of outstanding shares is the proposed sale?

Using the filing's figures, 5,000 shares is approximately 0.0068% of the reported 73,886,417 shares outstanding.

Does the filing state the filer knows of any undisclosed material information?

The notice includes the standard representation that the filer does not know any material adverse information about the issuer that has not been publicly disclosed.