InsiderTrades

Form 4 for ROOT Root, Inc.

Accepted 2025-05-23 00:00:00 ET · period of report 2025-05-21 · accession 0001104659-25-052560 · SEC index · Original document

Summary rows

Aggregated the way they appear in lists: one row per insider, transaction code and security table.

X Filed Traded Ticker Insider Title Type Price Qty Owned ΔOwn Value
DMI 2025-05-23 2025-05-21 ROOT Olsen Christopher 10% J - Other $0.00 -1.10M 339.9K -76% $0
DI 2025-05-23 2025-05-21 ROOT Olsen Christopher 10% C - Cnv Deriv — +1.44M 1.44M New —
DI 2025-05-23 2025-05-21 ROOT Olsen Christopher 10% C - Cnv Deriv $0.00 -1.44M 0 -100% $0

Purchase Sale Sale after option exercise All abbreviations

Every reported transaction

#TableSecurityDateCodeA/DSharesPriceOwned afterOwnExercise / expiryUnderlyingFootnotes
1 Common Class A Common Stock 2025-05-21 J A 6,869 $0.00 6,869 I See 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.
2 Common Class A Common Stock 2025-05-21 J D 1,443,376 $0.00 0 I See 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.
3 Common Class A Common Stock 2025-05-21 J A 339,856 $0.00 339,856 I See 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.
4 Common Class A Common Stock 2025-05-21 C A 1,443,376 — 1,443,376 I See 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. (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.
5 Derivative Class B Common Stock 2025-05-21 C D 1,443,376 $0.00 0 I See Footnote — · — to — 1,443,376 Class A Common Stock (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. (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.