[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Michael A. Eisenberg, a director of Lemonade, Inc. (LMND), reported a charitable donation of 4,000 shares of common stock on 09/12/2025, receiving no consideration. After the reported transaction his directly held shares total 200,452. He also reports indirect holdings of 89,331 shares held directly by Aleph-Aleph LP and 890,167 shares held directly by Aleph, L.P.; he states he may be deemed to share voting and investment power over those entity holdings but disclaims beneficial ownership except to the extent of his pecuniary interest. The Form 4 is signed by Eisenberg on 09/16/2025.

Positive

• Charitable donation of 4,000 shares indicates no sale pressure and no proceeds received.
• Substantial indirect holdings remain through Aleph-Aleph LP and Aleph, L.P., indicating continued economic interest.

Negative

• Direct holdings reduced by 4,000 shares to 200,452 shares following the donation.
• Potential governance ambiguity because the reporting person "may be deemed" to share voting and investment power over entity-held shares, though a disclaimer is included.

Insights

Corporate Governance Expert

TL;DR: Director donated a small number of shares; large indirect holdings remain and governance influence may persist.

The 4,000-share transfer is explicitly described as a charitable gift with no value received, which is routine and non-compensatory. More important for governance is the disclosure of substantial indirect holdings via Aleph entities totaling 979,498 shares, which could imply ongoing shared voting or investment power. The reporting person properly includes a disclaimer of beneficial ownership except for pecuniary interest, clarifying limited direct control despite the entity-level positions.

Securities Analyst

TL;DR: Transaction is immaterial to Lemonade's capitalization; indirect stakes dominate reported exposure.

The donated 4,000 shares reduce direct ownership to 200,452 shares, a modest change relative to the much larger indirect holdings (89,331 and 890,167). There is no cash proceeds or option exercise involved, and no derivative activity reported. From a market-impact perspective, this Form 4 discloses routine insider giving rather than a sale or economic disposition likely to affect supply or price.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Eisenberg Michael A

(Last) (First) (Middle)

5 CROSBY STREET

3RD FLOOR

(Street)

NEW YORK NY 10013

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Lemonade, Inc. [ LMND ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
09/12/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
COMMON STOCK	09/12/2025		G(1)		4,000	D	$0	200,452	D
COMMON STOCK								89,331	I	Directly held by Aleph-Aleph LP(2)
COMMON STOCK								890,167	I	Directly held by Aleph, L.P.(2)

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. This transaction represents a charitable donation to a third party. No value was received for the gifted shares.

2. The reporting person is a director of the entity that is the ultimate general partner of Aleph, L.P. and Aleph-Aleph, L.P. and the reporting person may be deemed to have shared voting and investment power over the shares held by each of these entities. The reporting person disclaims beneficial ownership of the shares held by each of these entities except to the extent of his pecuniary interest therein.

Remarks:

	/s/ Michael A. Eisenberg	09/16/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did Michael A. Eisenberg report on Form 4 for LMND?

He reported a charitable donation of 4,000 common shares on 09/12/2025, with no value received.

How many LMND shares does Eisenberg directly own after the transaction?

He directly holds 200,452 shares following the reported transaction.

Does Eisenberg have other holdings in LMND?

Yes. He reports 89,331 shares held by Aleph-Aleph LP and 890,167 shares held by Aleph, L.P., reported as indirect holdings.

Was any consideration received for the 4,000 shares?

No. The Form 4 states the shares were gifted to a third party and no value was received.

When was the Form 4 signed?

The filing is signed by Michael A. Eisenberg on 09/16/2025.