Sec Form 4 Filing - Olsen Christopher @ Root, Inc. - 2020-10-30

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 Olsen Christopher 2. Issuer Name and Ticker or Trading Symbol Root, Inc. [ ROOT] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) C/O ROOT, INC., 80 E RICH STREET, SUITE 500 3. Date of Earliest Transaction (MM/DD/YY) 10/30/2020 (Street) COLUMBUS, OH43215 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ 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 10/30/2020 C 51,178,410 A 51,178,410 I See footnote ( 5 ) Common Stock 10/30/2020 C 2,024,456 A 2,024,456 I See footnote ( 7 ) Common Stock 10/30/2020 C 978,891 A 978,891 I See footnote ( 8 ) Common Stock 10/30/2020 C 28,683 A 28,683 I See footnote ( 9 ) Common Stock ( 10 ) 10/30/2020 J 51,178,410 D 0 I See footnote ( 11 ) Common Stock ( 10 ) 10/30/2020 J 2,024,456 D 0 I See footnote ( 12 ) Common Stock ( 10 ) 10/30/2020 J 978,891 D 0 I See footnote ( 13 ) Common Stock ( 10 ) 10/30/2020 J 28,683 D 0 I See footnote ( 14 )

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 A-1 Preferred Stock ( 1 ) ( 1 ) 10/30/2020 C 14,949,360 ( 1 ) ( 1 ) Common Stock 14,949,360 $ 0 0 I See footnote ( 11 ) Series A-2 Preferred Stock ( 2 ) ( 2 ) 10/30/2020 C 13,602,870 ( 2 ) ( 2 ) Common Stock 13,602,870 $ 0 0 I See footnote ( 11 ) Series A-3 Preferred Stock ( 3 ) ( 3 ) 10/30/2020 C 10,447,860 ( 3 ) ( 3 ) Common Stock 10,447,860 $ 0 0 I See footnote ( 11 ) Series B Preferred Stock ( 4 ) ( 4 ) 10/30/2020 C 12,178,320 ( 4 ) ( 4 ) Common Stock 12,178,320 $ 0 0 I See footnote ( 11 ) Series E Preferred Stock ( 6 ) ( 6 ) 10/30/2020 C 2,024,456 ( 6 ) ( 6 ) Common Stock 2,024,456 $ 0 0 I See footnote ( 12 ) Series E Preferred Stock ( 6 ) ( 6 ) 10/30/2020 C 978,891 ( 6 ) ( 6 ) Common Stock 978,891 $ 0 0 I See footnote ( 13 ) Series E Preferred Stock ( 6 ) ( 6 ) 10/30/2020 C 28,683 ( 6 ) ( 6 ) Common Stock 28,683 $ 0 0 I See footnote ( 14 ) Class B Common Stock ( 10 ) ( 15 ) ( 15 ) 10/30/2020 J 51,178,410 ( 15 ) ( 15 ) Class A Common Stock 51,178,410 $ 0 51,178,410 I See footnote ( 5 ) Class B Common Stock ( 10 ) ( 15 ) ( 15 ) 10/30/2020 J 2,024,456 ( 15 ) ( 15 ) Class A Common Stock 2,024,456 $ 0 2,024,456 I See footnote ( 7 ) Class B Common Stock ( 10 ) ( 15 ) ( 15 ) 10/30/2020 J 978,891 ( 15 ) ( 15 ) Class A Common Stock 978,891 $ 0 978,891 I See footnote ( 8 ) Class B Common Stock ( 10 ) ( 15 ) ( 15 ) 10/30/2020 J 28,683 ( 15 ) ( 15 ) Class A Common Stock 28,683 $ 0 28,683 I See footnote ( 9 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Olsen Christopher C/O ROOT, INC. 80 E RICH STREET, SUITE 500 COLUMBUS, OH43215 X X Signatures /s/ Megan Binkley, Attorney-in-fact 11/03/2020 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The Series A-1 Preferred Stock automatically converted into Common Stock on a 1:1 basis immediately prior to the completion of the Issuer'sinitial public offering and had no expiration date. ( 2 )The Series A-2 Preferred Stock automatically converted into Common Stock on a 1:1 basis immediately prior to the completion of the Issuer's initial public offering and had no expiration date. ( 3 )The Series A-3 Preferred Stock automatically converted into Common Stock on a 1:1 basis immediately prior to the completion of the Issuer's initial public offering and had no expiration date. ( 4 )The Series B Preferred Stock automatically converted into Common Stock on a 1:1 basis immediately prior to the completion of the Issuer's initial public offering and had no expiration date. ( 5 )Shares are held of record by DC I Investment LLC ("DC I Investment"). Christopher Olsen is the Managing Director of DC I Investment and has sole voting and dispositive power with respect to the shares held of record by DC I Investment. ( 6 )The Series E Preferred Stock automatically converted into Common Stock on a 1:1 basis immediately prior to the completion of the Issuer's initial public offering and had no expiration date. ( 7 )Shares are held of record by Drive Capital Overdrive Fund I, L.P. ("Overdrive I"). Drive Capital Overdrive Fund I (GP), LLC ("Overdrive GP I") is the General Partner of Overdrive I. Christopher Olsen ("Olsen") and Mark Kvamme ("Kvamme") are the managing members of Overdrive GP I and share voting and dispositive power with respect to the shares held of record by Overdrive I. Overdrive GP I, Olsen and Kvamme disclaim beneficial ownership of such shares except to the extent of their pecuniary interests therein. ( 8 )Shares are held of record by Drive Capital Overdrive Fund I (TE), L.P. ("Overdrive TE I"). Drive Capital Overdrive Fund I (GP), LLC ("Overdrive GP I") is the General Partner of Overdrive TE I. Christopher Olsen ("Olsen") and Mark Kvamme ("Kvamme") are the managing members of Overdrive GP I and share voting and dispositive power with respect to the shares held of record by Overdrive TE I. Overdrive GP I, Olsen and Kvamme disclaim beneficial ownership of such shares except to the extent of their pecuniary interests therein. ( 9 )Shares are held of record by Drive Capital Overdrive Ignition Fund I, L.P. ("Overdrive Ignition I"). Drive Capital Overdrive Fund I (GP), LLC ("Overdrive GP I") is the General Partner of Overdrive Ignition I. Christopher Olsen ("Olsen") and Mark Kvamme ("Kvamme") are the managing members of Overdrive GP I and share voting and dispositive power with respect to the shares held of record by Overdrive Ignition I. Overdrive GP I, Olsen and Kvamme disclaim beneficial ownership of such shares except to the extent of their pecuniary interests therein. ( 10 )Immediately prior to the completion of the Issuer's initial public offering and following the conversion of each series of the Issuer's convertiblepreferred stock into Common Stock, each share of Common Stock was reclassified into one share of Class B Common Stock in an exempttransaction pursuant to Rule 16b-7. ( 11 )The shares were held of record by DC I Investment. ( 12 )The shares were held of record by Overdrive Fund I. ( 13 )The shares were held of record by Overdrive TE I. ( 14 )The shares were held of record by Overdrive Ignition I. ( 15 )Each share of Class B Common Stock is convertible into one share of Class A Common Stock at the option of the holder and has no expirationdate.

Remarks: This Form 4 is one of two Form 4s filed on the date hereof in respect of these transactions. The Designated Filer for the other Form 4 is Drive Capital Overdrive Fund I, L.P.

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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