Lemonade insider plans sale of 11,000 shares

Lemonade, Inc. (LMND) received a notice from shareholder John S. Peters of his intention to sell up to 11,000 shares of common stock through Fidelity Brokerage Services LLC on or after August 13, 2026.

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) received a notice from shareholder John S. Peters of his intention to sell up to 11,000 shares of common stock through Fidelity Brokerage Services LLC on or after August 13, 2026. The planned sale reflects an aggregate market value of $578,000.38 based on the reference price in the notice.

The filing also lists prior transactions: stock option exercises with the issuer on January 2, 2025 for 1,000 shares and April 2, 2025 for 10,000 shares, and open-market sales of 1,735, 3,608, and 3,444 common shares on June 3, June 4, and July 6, 2026, respectively, with corresponding dollar amounts disclosed.

Key Figures

Shares planned for sale: 11,000 shares Aggregate market value of planned sale: $578,000.38 Stock option exercise 1: 1,000 shares +4 more

7 metrics

Shares planned for sale 11,000 shares Common stock to be sold through Fidelity Brokerage Services LLC

Aggregate market value of planned sale $578,000.38 Value associated with 11,000 common shares proposed for sale

Stock option exercise 1 1,000 shares Common stock option exercise on January 2, 2025

Stock option exercise 2 10,000 shares Common stock option exercise on April 2, 2025

Sale on June 3, 2026 1,735 shares for $92,255.50 Common shares sold by John S. Peters

Sale on June 4, 2026 3,608 shares for $191,007.52 Common shares sold by John S. Peters

Sale on July 6, 2026 3,444 shares for $272,076.00 Common shares sold by John S. Peters

Key Terms

Form 144, Stock Option Exercise, aggregate market value

3 terms

Form 144 regulatory

"144: Securities To Be Sold"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Stock Option Exercise financial

"Common | 01/02/2025 | Stock Option Exercise | Issuer"

A stock option exercise is the act of using a previously granted right to buy shares of a company's stock at a specific, predetermined price by paying that price and receiving the shares. It matters to investors because exercising changes who owns the shares (which can dilute existing ownership), can trigger taxable events and shift potential gains or losses, and affects voting power and the company’s outstanding share count—like turning a voucher into an actual product that becomes part of circulating supply.

aggregate market value financial

"11000 | 578000.38 | 77396615 | 08/13/2026"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

FAQ

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

What does Lemonade (LMND) shareholder John S. Peters plan to sell under this Form 144?

John S. Peters plans to sell up to 11,000 shares of Lemonade common stock. The notice lists an aggregate market value of $578,000.38 for these shares, to be sold through Fidelity Brokerage Services LLC on or after August 13, 2026.

What is the approximate value of the LMND shares registered for sale in this Form 144?

The Form 144 indicates an aggregate market value of $578,000.38 for the 11,000 LMND common shares. This amount is based on the pricing reference used in the notice and reflects the value of the shares proposed to be sold.

When is the planned sale date for the LMND shares under this Form 144?

The planned sale date for the 11,000 LMND common shares is listed as August 13, 2026. This is the date associated with the proposed disposition of shares through Fidelity Brokerage Services LLC as disclosed in the notice.

Which broker will handle the proposed LMND share sale for John S. Peters?

The proposed sale of 11,000 LMND common shares will be handled by Fidelity Brokerage Services LLC. The broker’s address is given as 900 Salem Street, Smithfield, RI 02917, and the shares are listed for trading on the NYSE.

What LMND stock option exercises are disclosed for John S. Peters?

Two stock option exercises are disclosed: 1,000 shares exercised on January 2, 2025 and 10,000 shares exercised on April 2, 2025. Both were exercised with the issuer for cash and relate to LMND common stock.

What recent LMND share sales by John S. Peters are listed in the Form 144?

The notice lists three recent LMND sales: 1,735 shares for $92,255.50 on June 3, 2026; 3,608 shares for $191,007.52 on June 4, 2026; and 3,444 shares for $272,076.00 on July 6, 2026, all in Lemonade common stock.

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

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Accepted by SEC EDGAR 08/13/2026 - 12:57 PM EDT Learn about SEC filing dates

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	11000	578000.38	77396615	08/13/2026	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	01/02/2025	Stock Option Exercise	Issuer			1000	01/02/2025	Cash
Common	04/02/2025	Stock Option Exercise	Issuer			10000	04/02/2025	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 S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2026	1735	92255.50
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	06/04/2026	3608	191007.52
John S. Peters 5 Crosby Street 3rd Floor New York NY 10013	Common	07/06/2026	3444	272076.00

144: Remarks and Signature

Remarks
Date of Notice	08/13/2026
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/ Jared Cook, 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)