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

Reporting relationship: 10%+ Owner
Issuer ticker: ROOT
Reported as of: 21 May 2025
Net transaction value: $0
SEC form: 4
Accepted by SEC: 23 May 2025, 20:52:00 UTC
Prior SEC filing: 02 Sep 2022
Source filing: View source filing
Reporting owner signature: /s/ Christopher Olsen

Key filing fact

Christopher Olsen filed Form 4 for Root, Inc. (ROOT) on 23 May 2025.

Key facts

This page summarizes Christopher Olsen's Form 4 filing for Root, Inc. (ROOT).
5 reported transactions and 1 derivative row are listed below.
Accepted by SEC: 23 May 2025, 20:52.

Change

Previous filing in this sequence was filed on 02 Sep 2022.
Current net transaction value: $0.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001828005 Primary reporting owner

Olsen Christopher

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

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

ROOT transaction

Class A Common Stock

Conversion of derivative security

Transaction value
Shares: +1,443,376
Change %
Price
Shares after: 1,443,376
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F1, F2

ROOT transaction

Class A Common Stock

Other

Transaction value: $0
Shares: -1,443,376
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F2, F3

ROOT transaction

Class A Common Stock

Other

Transaction value: $0
Shares: +339,856
Change %
Price: $0.000000
Shares after: 339,856
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F4, F5

ROOT transaction

Class A Common Stock

Other

Transaction value: $0
Shares: +6,869
Change %
Price: $0.000000
Shares after: 6,869
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F4, F6

ROOT holding

Class A Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 6,288
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F7

ROOT holding

Class A Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 112,469
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F8

ROOT holding

Class A Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 54,382
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F9

ROOT holding

Class A Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 1,593
Date: 21 May 2025
Ownership: See Footnote
Footnotes: F10

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

ROOT transaction Derivative

Class B Common Stock

Conversion of derivative security

Transaction value: $0
Shares: -1,443,376
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 21 May 2025
Ownership: See Footnote
Underlying class: Class A Common Stock
Underlying amount: 1,443,376
Exercise price
Footnotes: F2, F11

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Section 16 status

Christopher Olsen is no longer subject to Section 16 filing requirements. Form 4 or Form 5 obligations may still apply in specific circumstances.

Explanation of responses 11 footnotes

Footnote F1

These shares were converted from Class B Common Stock into Class A Common Stock on a one-for-one basis for no consideration.

Footnote 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.

Footnote 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.

Footnote F4

The shares were obtained pursuant to a pro-rata distribution from DC I Investment, for no consideration.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

Footnote 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.

SEC 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.