Christopher Olsen - 21 May 2025 Form 4 Insider Report for Root, Inc. (ROOT)

Role
10%+ Owner
Signature
/s/ Christopher Olsen
Issuer symbol
ROOT
Transactions as of
21 May 2025
Net transactions value
$0
Form type
4
Filing time
23 May 2025, 20:52:00 UTC
Previous filing
02 Sep 2022

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
Olsen Christopher 10%+ Owner 629 N. HIGH STREET, 6TH FLOOR, COLUMBUS /s/ Christopher Olsen 23 May 2025 0001828005

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 +1,443,376 1,443,376 21 May 2025 See Footnote F1, F2
transaction ROOT Class A Common Stock Other $0 -1,443,376 -100% $0.000000 0 21 May 2025 See Footnote F2, F3
transaction ROOT Class A Common Stock Other $0 +339,856 $0.000000 339,856 21 May 2025 See Footnote F4, F5
transaction ROOT Class A Common Stock Other $0 +6,869 $0.000000 6,869 21 May 2025 See Footnote F4, F6
holding ROOT Class A Common Stock 6,288 21 May 2025 See Footnote F7
holding ROOT Class A Common Stock 112,469 21 May 2025 See Footnote F8
holding ROOT Class A Common Stock 54,382 21 May 2025 See Footnote F9
holding ROOT Class A Common Stock 1,593 21 May 2025 See Footnote F10

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

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction ROOT Class B Common Stock Conversion of derivative security $0 -1,443,376 -100% $0.000000 0 21 May 2025 Class A Common Stock 1,443,376 See Footnote F2, F11
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Christopher Olsen is no longer subject to Section 16 filing requirements. Form 4 or Form 5 obligations may continue.

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"). The Reporting Person 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 a pro-rata, in-kind distribution by DC I Investment to its indirect equity holders, without additional consideration. DC I Investment distributed an aggregate of 1,103,520 shares to the limited partners of its two members, Drive Capital Fund I, L.P. ("Fund I") and Drive Capital Ignition Fund I, L.P. ("Ignition Fund I") and 339,856 shares to the general partner of Fund I and Ignition Fund I, Drive Capital I (GP), LLC ("GP I"), on a pro rata basis.
F4 The shares were obtained pursuant to a pro-rata distribution from DC I Investment, for no consideration.
F5 The shares are held of record by GP I. The Reporting Person is the managing member of GP I and has voting and dispositive power with respect to the shares held of record by GP I. The Reporting Person disclaims beneficial ownership of such shares except to the extent of his pecuniary interest therein.
F6 The shares are held of record by Dwight H. Hibbard Family Trust f/b/o Christoper Olsen - Exempt (the "Trust"). The Reporting Person is the Trustee of the Trust and has sole voting and dispositive power with respect to the shares held of record by the Trust.
F7 The shares are held of record by Purple Dot LLC ("Purple Dot"). The Reporting Person is the Managing Member of Purple Dot and has sole voting and dispositive power with respect to the shares held of record by Purple Dot. On February 26, 2024, Purple Dot obtained 12,576 shares pursuant to a pro-rata, in-kind distribution by GP I, and on March 6, 2024, Purple Dot transferred 6,288 shares to the Reporting Person's ex-spouse pursuant to a domestic relations order. These two prior transactions were exempt from reporting under Section 16 and therefore were not included in previous Form 4 filings.
F8 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. The Reporting Person is the managing member of Overdrive GP I and has voting and dispositive power with respect to the shares held of record by Overdrive I. Overdrive GP I and the Reporting Person disclaim beneficial ownership of such shares except to the extent of their pecuniary interests therein.
F9 The shares are held of record by Drive Capital Overdrive Fund I (TE), L.P. ("Overdrive TE I"). Overdrive GP I is the General Partner of Overdrive TE I. The Reporting Person is the managing member of Overdrive GP I and has voting and dispositive power with respect to the shares held of record by Overdrive TE I. Overdrive GP I and the Reporting Person disclaim beneficial ownership of such shares except to the extent of their pecuniary interests therein.
F10 The shares are held of record by Drive Capital Overdrive Ignition Fund I, L.P. ("Overdrive Ignition I"). Overdrive GP I is the General Partner of Overdrive Ignition I. The Reporting Person is the managing member of Overdrive GP I and has voting and dispositive power with respect to the shares held of record by Overdrive Ignition I. Overdrive GP I and the Reporting Person disclaim beneficial ownership of such shares except to the extent of their pecuniary interests therein.
F11 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.

Remarks:

This Form 4 is one of two Form 4s filed on the date hereof with respect to the conversion and distribution of these shares. The Reporting Persons for the other Form 4 are Overdrive I, Overdrive TE I, Overdrive Ignition, GP I and Overdrive GP I.