Christopher Olsen - 17 May 2021 Form 4 Insider Report for Root, Inc. (ROOT)

Role: Director, 10%+ Owner
Signature: /s/ Christopher Olsen
Issuer symbol: ROOT
Transactions as of: 17 May 2021
Net transactions value: $0
Form type: 4
Filing time: 09 Jun 2021, 13:18:14 UTC
Next filing: 14 Jun 2021
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ROOT	Class A Common Stock	Conversion of derivative security		+5,117,841			5,117,841	17 May 2021	See Footnote	F1, F2
transaction	ROOT	Class A Common Stock	Award	$0	+15,290		$0.000000	15,290	08 Jun 2021	Direct	F3

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Ownership	Footnotes
transaction	ROOT	Class B Common Stock	Conversion of derivative security	$0	-5,117,841	-10%	$0.000000	46,060,569	17 May 2021	Class A Common Stock	5,117,841	See Footnote	F2, F4
holding	ROOT	Class B Common Stock						2,024,456	17 May 2021	Class A Common Stock	2,024,456	See Footnote	F4, F5
holding	ROOT	Class B Common Stock						978,891	17 May 2021	Class A Common Stock	978,891	See Footnote	F4, F6
holding	ROOT	Class B Common Stock						28,683	17 May 2021	Class A Common Stock	28,683	See Footnote	F4, F7

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	These shares were converted from Class B Common Stock into Class A Common Stock on a one-for-one basis for no consideration.
F2	The 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.
F3	Represents the grant of restricted stock units ("RSUs") to the Reporting Person for no consideration. The shares subject to the RSUs vest on the date of the Issuer's 2022 annual meeting.
F4	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 expiration date.
F5	The 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.
F6	The 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.
F7	The 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.

Remarks:

This Form 4 is one of two Form 4s filed on the date hereof with respect to the conversion of the Class B Common Stock to Class A Common Stock. The Reporting Person for the other Form 4 is Drive Capital Overdrive Fund I, L.P.