Root, Inc. — Director's Dealing 2020

Nov 4, 2020

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Root, Inc. (ROOT)
CIK: 0001788882
Period of Report: 2020-10-30

Reporting Person: Olsen Christopher (Director, 10% Owner)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2020-10-30	Common Stock	C	51178410	—	Acquired	51178410	Indirect
2020-10-30	Common Stock	C	2024456	—	Acquired	2024456	Indirect
2020-10-30	Common Stock	C	978891	—	Acquired	978891	Indirect
2020-10-30	Common Stock	C	28683	—	Acquired	28683	Indirect
2020-10-30	Common Stock	J	51178410	—	Disposed	0	Indirect
2020-10-30	Common Stock	J	2024456	—	Disposed	0	Indirect
2020-10-30	Common Stock	J	978891	—	Disposed	0	Indirect
2020-10-30	Common Stock	J	28683	—	Disposed	0	Indirect

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2020-10-30	Series A-1 Preferred Stock	$	C	14949360	Disposed		Common Stock (14949360)	Indirect
2020-10-30	Series A-2 Preferred Stock	$	C	13602870	Disposed		Common Stock (13602870)	Indirect
2020-10-30	Series A-3 Preferred Stock	$	C	10447860	Disposed		Common Stock (10447860)	Indirect
2020-10-30	Series B Preferred Stock	$	C	12178320	Disposed		Common Stock (12178320)	Indirect
2020-10-30	Series E Preferred Stock	$	C	2024456	Disposed		Common Stock (2024456)	Indirect
2020-10-30	Series E Preferred Stock	$	C	978891	Disposed		Common Stock (978891)	Indirect
2020-10-30	Series E Preferred Stock	$	C	28683	Disposed		Common Stock (28683)	Indirect
2020-10-30	Class B Common Stock	$	J	51178410	Acquired		Class A Common Stock (51178410)	Indirect
2020-10-30	Class B Common Stock	$	J	2024456	Acquired		Class A Common Stock (2024456)	Indirect
2020-10-30	Class B Common Stock	$	J	978891	Acquired		Class A Common Stock (978891)	Indirect
2020-10-30	Class B Common Stock	$	J	28683	Acquired		Class A Common Stock (28683)	Indirect

Footnotes

F1: The Series A-1 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.

F2: 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.

F3: 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.

F4: 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.

F5: 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.

F6: 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.

F7: 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.

F8: 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.

F9: 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.

F10: Immediately prior to the completion of the Issuer's initial public offering and following the conversion of each series of the Issuer's convertible
preferred stock into Common Stock, each share of Common Stock was reclassified into one share of Class B Common Stock in an exempt
transaction pursuant to Rule 16b-7.

F11: The shares were held of record by DC I Investment.

F12: The shares were held of record by Overdrive Fund I.

F13: The shares were held of record by Overdrive TE I.

F14: The shares were held of record by Overdrive Ignition I.

F15: 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.