[Form 4] Lemonade, Inc. Insider Trading Activity

Rhea-AI Filing Summary

UWM Holdings Corp. (UWMC) – Form 4 insider transaction summary

• Insider: Mat Ishbia, President, CEO, Director and 10% owner (through SFS Corp).
• Transaction window: 5-7 Aug 2025 under a Rule 10b5-1 trading plan adopted 17 Mar 2025.
• Shares sold: 1,200,108 Class A shares in three equal blocks of 400,036.
• Weighted-avg sale prices: $4.31 (8/5), $4.25 (8/6), $4.61 (8/7).
• Shares remaining at SFS Corp: 2,698,704 after the 8/7 sale.
• Direct holdings: 279,989 Class A shares.
• Derivative holdings: 180,737 RSUs, vesting 1 Mar 2026 on a 1-for-1 basis.

The filing discloses sizable, sequential insider sales representing a reduction of approximately 31% of SFS Corp’s reported Class A stake over three days. All transactions were executed automatically under a pre-arranged 10b5-1 plan, which can lessen but not eliminate market concern regarding insider intent. No purchases or option exercises were reported, and there were no changes to Ishbia’s RSU position. Investors often view large dispositions by a founder-CEO as a potential negative sentiment signal, though the continued ownership of roughly 2.7 million shares plus unvested RSUs maintains significant alignment.

Insights

Equity Analyst

TL;DR: CEO sold 1.2 M shares (~$5 M) via 10b5-1, trimming stake by one-third—moderately negative signal.

The three back-to-back sales totaling 1.2 million shares at $4.25-$4.61 generated roughly $5.2 million in proceeds. Although executed under a 10b5-1 plan, the magnitude—about 31% of SFS Corp’s reported holdings—could pressure sentiment and add float. Ishbia still controls 2.7 million shares plus 279.9 k directly and 180.7 k RSUs, so alignment remains, but the sales reduce perceived insider conviction. No other corporate events accompany the filing, suggesting sales are liquidity-driven rather than strategic. Overall impact: mildly negative.

Governance Specialist

TL;DR: Large planned sales raise governance optics but remain Rule 10b5-1 compliant.

Use of a disclosed 10b5-1 plan provides a safe-harbor defense and limits information-asymmetry concerns. Nevertheless, founder-CEO sales of this size often draw scrutiny, especially ahead of key corporate milestones not referenced here. The filing reinforces transparency—weighted-average ranges and footnote details are provided—but boards should monitor cumulative dispositions to ensure continued ownership alignment. Impact rated slightly negative due to potential perception risks.

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).

X

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^*

Eckstein Adina

(Last) (First) (Middle)

C/O LEMONADE, INC.

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)

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

3. Date of Earliest Transaction (Month/Day/Year)
08/05/2025

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	08/05/2025		M		1,250	A	$23.69	190,903	D
COMMON STOCK	08/05/2025		M		3,750	A	$23.69	194,653	D
COMMON STOCK	08/05/2025		S(1)		5,000	D	$49	189,653	D

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
STOCK OPTION	$23.69	08/05/2025		M			1,250	(2)	09/25/2029	COMMON STOCK	1,250	$23.69	0	D
STOCK OPTION	$24.47	08/05/2025		M			3,750	(2)	06/06/2030	COMMON STOCK	3,750	$24.47	26,250	D

Explanation of Responses:

1. Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 5, 2024.

2. The stock option is fully vested.

Remarks:

	/s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein	08/07/2025
	** 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

How many UWMC shares did CEO Mat Ishbia sell in August 2025?

He sold 1,200,108 Class A shares over 5-7 Aug 2025 in three equal blocks of 400,036 shares.

At what prices were the UWMC shares sold?

Weighted-average prices were $4.31 on 8/5, $4.25 on 8/6, and $4.61 on 8/7 2025.

Does Mat Ishbia still hold UWMC stock after the sales?

Yes. SFS Corp holds 2,698,704 shares; Ishbia directly owns 279,989 shares and 180,737 RSUs vesting in 2026.

Were the transactions part of a 10b5-1 trading plan?

Yes. All sales were executed under a Rule 10b5-1 plan adopted on 17 Mar 2025.

What could the insider sales mean for UWMC investors?

Large insider dispositions often weigh on sentiment, though a 10b5-1 plan may indicate pre-planned liquidity rather than a shift in outlook.