Sec Form 4 Filing - General Catalyst Group Management Holdings GP, LLC @ Lemonade, Inc. - 2020-07-07

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 Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person General Catalyst Group Management Holdings GP, LLC 2. Issuer Name and Ticker or Trading Symbol Lemonade, Inc. [ LMND] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 20 UNIVERSITY ROAD, 4TH FLOOR 3. Date of Earliest Transaction (MM/DD/YY) 07/07/2020 (Street) CAMBRIDGE, MA02138 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) _____ Form filed by One Reporting Person __ X __ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 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 07/07/2020 C 1,492,691 ( 1 ) A 1,492,691 I Directly held by General Catalyst Group VIII, L.P. ( 2 ) ( 3 ) Common Stock 07/07/2020 C 1,729,622 ( 1 ) A 1,729,622 I Directly held by General Catalyst Group VIII Supplemental, L.P. ( 2 ) ( 3 )

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 (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 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 (MM/DD/YY) 7. Title and Amount of Underlying Securities (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 Series B Preferred Stock ( 1 ) 07/07/2020 C 1,157,621 ( 1 ) ( 1 ) Common Stock 1,157,621 ( 1 ) 0 I Directly held by General Catalyst Group VIII, L.P. ( 2 ) ( 3 ) Series B Preferred Stock ( 1 ) 07/07/2020 C 1,157,621 ( 1 ) ( 1 ) Common Stock 1,157,621 ( 1 ) 0 I Directly held by General Catalyst Group VIII Supplemental, L.P. ( 2 ) ( 3 ) Series C Preferred Stock ( 1 ) 07/07/2020 C 335,070 ( 1 ) ( 1 ) Common Stock 335,070 ( 1 ) 0 I Directly held by General Catalyst Group VIII, L.P. ( 2 ) ( 3 ) Series C Preferred Stock ( 1 ) 07/07/2020 C 335,070 ( 1 ) ( 1 ) Common Stock 335,070 ( 1 ) 0 I Directly held by General Catalyst Group VIII Supplemental, L.P. ( 2 ) ( 3 ) Series D Preferred Stock ( 1 ) 07/07/2020 C 236,931 ( 1 ) ( 1 ) Common Stock 236,931 ( 1 ) 0 I Directly held by General Catalyst Group VIII Supplemental, L.P. ( 2 ) ( 3 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other General Catalyst Group Management Holdings GP, LLC 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X General Catalyst Group Management Holdings, L.P. 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X General Catalyst Group Management, LLC 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X General Catalyst GP VIII, LLC 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X General Catalyst Partners VIII, L.P. 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X General Catalyst Group VIII, L.P. 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X General Catalyst Group VIII Supplemental, L.P. 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X CHENAULT KENNETH I 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X Taneja Hemant 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X Fialkow David P 20 UNIVERSITY ROAD, 4TH FLOOR CAMBRIDGE, MA02138 X Signatures General Catalyst Group Management Holdings GP, LLC; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date General Catalyst Group Management Holdings, L.P.; By: General Catalyst Group Management Holdings GP, LLC; its General Partner; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date General Catalyst Group Management, LLC; By: General Catalyst Group Management Holdings, L.P.; its Manager; By: General Catalyst Group Management Holdings GP, LLC; its Managing Member; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date General Catalyst GP VIII, LLC; By: General Catalyst Group Management, LLC, its Manager; By: General Catalyst Group Management Holdings, L.P., its Manager; By: its General Partner; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date General Catalyst Partners VIII, L.P.; By: General Catalyst GP VIII, LLC, its general partner; By: General Catalyst Group Management, LLC, its Manager; By: its Manager; By: its General Partner; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date General Catalyst Group VIII, L.P.; By: General Catalyst Partners VIII, L.P., its General Partner; By: its general partner; By: its Manager; By: its Manager; By: its General Partner; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date General Catalyst Group VIII Supplemental, L.P.; By: General Catalyst Partners VIII, L.P., its General Partner; By: its general partner; By: its Manager; By: its Manager; By: its General Partner; By: /s/ Christopher McCain, Chief Legal Officer 07/08/2020 Signature of Reporting Person Date /s/ Christopher McCain, attorney-in-fact for Kenneth Chenault 07/08/2020 Signature of Reporting Person Date /s/ Christopher McCain, attorney-in-fact for Hemant Taneja 07/08/2020 Signature of Reporting Person Date /s/ Christopher McCain, attorney-in-fact for David Fialkow 07/08/2020 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Upon the closing of the Issuer's initial public offering, each share of preferred stock automatically converted into shares of the Issuer's common stock on a one-for-one basis. ( 2 )General Catalyst GP VIII, LLC ("GC VIII LLC") is the general partner of General Catalyst Partners VIII, L.P. ("GC VIII LP"), which is the general partner of General Catalyst Group VIII, L.P. ("CG Group VIII") and General Catalyst Group VIII Supplemental, L.P. ("CG 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. ( 3 )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, each Reporting Person disclaims beneficial ownership over such shares except to the extent of his or its pecuniary interest therein, if any. A Form 4 is being filed separately by Mr. Cutler in his capacity as a director of the Issuer.

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).

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