Root, Inc. — Director's Dealing 2020

Oct 28, 2020

SEC Form 3 — Initial Statement of Beneficial Ownership

Issuer: Root, Inc. (ROOT)
CIK: 0001788882
Period of Report: 2020-10-27

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

Holdings (Derivative)

Security	Exercise Price	Expiration	Underlying	Shares	Ownership
Series A-1 Preferred Stock	$		Common Stock (14949360)		Indirect
Series A-2 Preferred Stock	$		Common Stock (13602870)		Indirect
Series A-3 Preferred Stock	$		Common Stock (10447860)		Indirect
Series B Preferred Stock	$		Common Stock (12178320)		Indirect
Series E Preferred Stock	$		Common Stock (2024456)		Indirect
Series E Preferred Stock	$		Common Stock (978891)		Indirect
Series E Preferred Stock	$		Common Stock (28683)		Indirect

Footnotes

F1: Each share of Series A-1 Preferred Stock, Series A-2 Preferred Stock, Series A-3 Preferred Stock, Series B Preferred Stock and Series E Preferred Stock is convertible into Common Stock on a 1:1 basis and has no expiration date. Immediately prior to the completion of the Issuer's initial public offering, all shares of Series A-1 Preferred Stock, Series A-2 Preferred Stock, Series A-3 Preferred Stock, Series B Preferred Stock and Series E Preferred Stock will be converted into shares of Common Stock.

F2: Each share of Common Stock shall be reclassified into one share of Class B Common Stock immediately prior to the completion of the Issuer's initial public offering of Class A Common Stock.

F3: 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.

F4: 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.

F5: 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.

F6: 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.