LMND Lemonade Inc

FORM 4 [ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES                                                                                   
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940                       

1. Name and Address of Reporting Person * Cutler Joel E	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)
(Last)          (First)          (Middle) 20 UNIVERSITY ROAD, 4TH FLOOR	3. Date of Earliest Transaction (MM/DD/YYYY) 6/2/2021
(Street) CAMBRIDGE, MA 02138 (City)        (State)        (Zip)	4. If Amendment, Date Original Filed (MM/DD/YYYY)	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. Trans. Date	2A. Deemed Execution Date, if any	3. Trans. 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	6/2/2021		S		3907	D	$96.4360 (1)	951415	I	Directly held by General Catalyst Group VIII, L.P. (2)
Common Stock	6/2/2021		S		207031	D	$97.2594 (3)	744384	I	Directly held by General Catalyst Group VIII, L.P. (2)
Common Stock	6/2/2021		S		46416	D	$97.7462 (4)	697968	I	Directly held by General Catalyst Group VIII, L.P. (2)
Common Stock	6/2/2021		S		4527	D	$96.4360 (1)	1102430	I	Directly held by General Catalyst Group VIII Supplemental, L.P. (2)
Common Stock	6/2/2021		S		239893	D	$97.2594 (3)	862537	I	Directly held by General Catalyst Group VIII Supplemental, L.P. (2)
Common Stock	6/2/2021		S		53783	D	$97.7462 (4)	808754	I	Directly held by General Catalyst Group VIII Supplemental, L.P. (2)
Common Stock								11428	D
Common Stock								1440	I	See footnote (5)

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Trans. Date	3A. Deemed Execution Date, if any	4. Trans. 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		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 of Derivative Security: 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)	The price reported in Column 4 is a weighted average price. The shares were sold in multiple transactions at prices ranging from $95.72 to $96.68, inclusive. The Reporting Person undertakes to provide the Issuer, any security holder, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote and in footnotes (3) through (4) of this Form 4.
(2)	General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P., which is the general partner of General Catalyst Group VIII, L.P. ("GC Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("GC Group VIII Supplemental"). General Catalyst Group Management, LLC ("GCGM") is the manager of GC VIII LLC. General Catalyst Group Management Holdings, L.P. ("GCGMH") is the manager of GCGM. General Catalyst Group Management Holdings GP, LLC ("GCGMH LLC") is the general partner of GCGMH. Each of Kenneth Chenault, Joel Cutler, David Fialkow, and Hemant Taneja is a managing director of GCGMH LLC and shares voting and investment power over the shares held by GC Group VIII and GC Group VIII Supplemental. However, the reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.
(3)	The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $96.68 to $97.63, inclusive.
(4)	The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $97.64 to $98.04, inclusive.
(5)	Held by Joel E. Cutler Family 2012 GST Trust. The reporting person's spouse is a trustee of the trust. The reporting person disclaims beneficial ownership over such shares except to the extent of his pecuniary interest therein, if any.

Reporting Owners
Reporting Owner Name / Address	Relationships
	Director	10% Owner	Officer	Other
Cutler Joel E 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA 02138	X

Signatures
/s/ Christopher McCain, Attorney-in-Fact for Joel Cutler		6/4/2021
**Signature of Reporting Person		Date