LMND insider plans Rule 144 sale of 10,000 common shares

LMND – Planned insider sale under Rule 144 An affiliate of the issuer has filed a notice to sell 10,000 shares of common stock through Fidelity Brokerage Services on the NYSE, with an approximate sale date of 01/06/2026.

Accepted by SEC EDGAR 01/06/2026 - 02:36 PM EST Learn about SEC filing dates

Rhea-AI Filing Summary

LMND – Planned insider sale under Rule 144

An affiliate of the issuer has filed a notice to sell 10,000 shares of common stock through Fidelity Brokerage Services on the NYSE, with an approximate sale date of 01/06/2026. The filing shows 74,731,027 common shares outstanding for the issuer.

The 10,000 shares to be sold were acquired on 12/31/2024 via a stock option exercise from the issuer, paid in cash. Over the past three months, the filer, identified as John S. Peters of New York, has already sold several blocks of common shares, including 18,930 shares for gross proceeds of $1,377,536.10 on 11/20/2025, along with multiple smaller trades in late November and December 2025.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the LMND Rule 144 filing disclose?

The filing discloses that an insider plans to sell 10,000 shares of LMND common stock on or around 01/06/2026 through Fidelity Brokerage Services LLC on the NYSE.

How were the LMND shares in this Rule 144 filing acquired?

The 10,000 LMND common shares were acquired on 12/31/2024 via a stock option exercise from the issuer, with the purchase price paid in cash.

How many LMND shares are currently outstanding according to this notice?

According to the notice, the issuer has 74,731,027 shares of common stock outstanding.

Who is selling LMND shares under this Rule 144 notice?

The seller identified in the filing is John S. Peters, with an address in New York, who is selling LMND common stock for his account.

What recent LMND share sales by this insider are reported?

Over the past three months, John S. Peters sold several blocks of LMND common stock, including 18,930 shares for $1,377,536.10 on 11/20/2025, plus additional sales on 11/24/2025, 12/02/2025, 12/03/2025, and 12/10/2025.

What representation does the LMND insider make in this Rule 144 filing?

By signing the notice, the insider represents that they do not know any material adverse information about the issuer's current or prospective operations that has not been publicly disclosed.

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

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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	0001816299
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	Lemonade, Inc.
SEC File Number	001-39367
Address of Issuer	5 CROSBY STREET 3RD FLOOR NEW YORK NEW YORK 10013
Phone	(844) 733-8666
Name of Person for Whose Account the Securities are To Be Sold	Peters John Sheldon
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	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	10000	800000.00	74731027	01/06/2026	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	12/31/2024	Stock Option Exercise	Issuer			10000	12/31/2024	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 S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	11/20/2025	18930	1377536.10
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	11/24/2025	3798	278205.02
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	12/02/2025	2677	194711.06
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	12/03/2025	2667	193010.79
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	12/10/2025	3554	287874.00

144: Remarks and Signature

Remarks
Date of Notice	01/06/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	08/22/2025
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	/s/ Gary Redman, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for John S. Peters
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)