Lemonade Insider Files to Divest 11k Shares; Prior Sales Top $1.39M

Rhea-AI Filing Summary

Form 144 filing for Lemonade, Inc. (LMND) discloses a proposed sale of 11,000 common shares through Fidelity Brokerage Services on 06/30/2025. The shares carry an aggregate market value of $469,590, implying an indicative price of roughly $42.69 per share. Outstanding shares reported in the filing total 73,266,170, so the planned sale represents about 0.015 % of shares outstanding, a de-minimis ownership impact.

The form also summarizes insider activity over the preceding three months. Six transactions executed by Timothy E. Bixby between 06/03/2025 and 06/23/2025 amounted to 33,916 shares sold, yielding gross proceeds of ≈$1.394 million. Combining those sales with the new notice brings total disclosed dispositions to 44,916 shares since early June 2025.

While the filing does not list the seller’s formal relationship to the company, the repeated sales could signal ongoing personal liquidity moves or portfolio rebalancing. From a capital-structure perspective, the quantities are immaterial; however, continuing insider divestitures may weigh modestly on near-term investor sentiment.

Positive

• Minimal dilution risk: proposed 11,000-share sale equals only 0.015 % of LMND’s outstanding shares, leaving share count effectively unchanged.

Negative

• Continued insider selling: the same seller has disclosed 33,916 shares sold over the prior three months and plans to sell an additional 11,000 shares, which may dampen investor sentiment.

Insights

Financial Analyst

TL;DR: Minor Form 144: 11k LMND shares for ~$470k; prior 3-month insider sales total 33.9k shares—immaterial float impact, slightly negative sentiment.

The notice records a small planned disposition relative to Lemonade’s 73.3 million shares outstanding. Even when aggregated with the recent 33.9 k-share insider sales, the cumulative 44.9 k shares equal roughly 0.06 % of the float—too small to alter supply-demand dynamics or valuation models. No financial performance details, guidance changes, or strategic shifts accompany the filing, so the operating outlook is unchanged. Nonetheless, serial sales by the same individual can create a perception of weakened insider conviction, marginally pressuring sentiment. On balance, the disclosure is operationally neutral but optically modestly negative.

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	11000	469590.00	73266170	06/30/2025	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	06/30/2025	Option Granted - 12/01/2019	Issuer			11000	06/30/2025	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

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

How many Lemonade (LMND) shares are being sold under this Form 144?

The filing covers 11,000 common shares of Lemonade, Inc.

What is the aggregate market value of the shares to be sold?

The 11,000 shares have an aggregate market value of $469,590 according to the notice.

When is the planned sale date for the LMND shares?

The approximate sale date listed is 06/30/2025.

How many LMND shares has the seller disposed of in the last three months?

The filing reports 33,916 shares sold between 06/03/2025 and 06/23/2025.

What percentage of Lemonade’s outstanding shares does the new sale represent?

11,000 shares represent about 0.015 % of the reported 73,266,170 shares outstanding.

Which broker will handle the transaction?

The shares are to be sold through Fidelity Brokerage Services LLC.