[144] Lemonade, Inc. SEC Filing

Rhea-AI Filing Summary

Lemonade, Inc. (LMND) – Form 144 notice of proposed insider sale

A filer identified in the past-sales table as Timothy E. Bixby intends to sell 1,000 common shares on 21-Jul-2025 through Fidelity Brokerage Services on the NYSE. At the stated price of $42.70, the transaction’s aggregate market value is $42,700, equal to roughly 0.0014 % of Lemonade’s 73,266,170 shares outstanding.

The filing also lists 10 sales over the prior three months totaling 66,916 shares and generating an estimated $2.78 million in gross proceeds. Individual sale sizes ranged from 1,916 to 11,000 shares. The shares now being offered were acquired via an employee option granted 01-Dec-2019 and are to be paid for in cash on the sale date.

• Form type: 144 (Rule 144 resale)
• Broker: Fidelity Brokerage Services LLC
• Class: Common stock
• No financial performance data or corporate updates accompanied the notice.

Insights

Securities Analyst

TL;DR: Continued insider selling (~67k shares) may pressure sentiment despite small percent of float.

The filer has already liquidated 66,916 LMND shares for roughly $2.8 million in the last three months and now seeks to dispose of another 1,000 shares. While this represents a negligible fraction of outstanding shares, the pace and frequency of sales could be interpreted as a lack of confidence or simple diversification by the insider. With no offsetting corporate news, the market may view the pattern as modestly bearish. The filing is therefore impactful mainly for sentiment, not fundamentals.

Risk Analyst

TL;DR: Low float impact, but repeated insider sales flag incremental governance risk.

From a governance standpoint, serial insider disposals warrant monitoring. Although 1,000 shares is immaterial to float, cumulative sales signal opportunistic profit-taking near $42–43 per share. Investors should evaluate whether sales align with pre-set 10b5-1 plans; the filing leaves the 10b5-1 checkbox blank. Absent clarification, perceived information asymmetry risk rises slightly, justifying a cautious stance until further disclosure.

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	1000	42700.00	73266170	07/21/2025	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	07/21/2025	Option Granted - 12/01/2019	Issuer			1000	07/21/2025	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
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/03/2025	1916	67540.92
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/05/2025	5000	187500.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/09/2025	5000	201500.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/11/2025	6000	255000.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/16/2025	5000	205300.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/23/2025	11000	476960.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	06/30/2025	11000	469590.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York` NY 10013	Common	07/07/2025	11000	466400.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	07/14/2025	5000	190800.00
Timothy E. Bixby 5 Crosby Street 3rd Floor New York NY 10013	Common	07/18/2025	6000	255000.00

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)