Root, Inc. SEC Filings

Root, Inc. reporting person Forish Ryan, identified as the company's Chief Accounting Officer, reported a transaction on 09/15/2025 related to Class A common stock. The Form 4 shows 499 shares were disposed of (transaction code F) at a price of $100.20 per share. The filing explains these shares were withheld by the issuer to satisfy tax withholding arising from the vesting of restricted stock units. After the withholding, Mr. Ryan beneficially owned 21,772 shares directly. The form is signed on behalf of the reporting person by an attorney-in-fact on 09/16/2025.

Root, Inc. (ROOT) Form 4 reports insider sales by Timm Alexander E., the company's Chief Executive Officer, Director and 10% owner. The filing shows four separate dispositions on 09/02/2025 executed pursuant to a 10b5-1 trading plan, totaling 10,861 shares of Class A common stock. Reported sale prices ranged across four tranches from approximately $87.875 to $90.39. After these transactions the reporting person beneficially owned 157,748 shares of Class A common stock. The filing was signed by an attorney-in-fact on behalf of the reporting person.

Mahtiyar Bonakdarpour, President and CTO of Root, Inc. (ROOT), reported a sale of 5,750 Class A common shares on 09/02/2025 at $89.74 per share executed pursuant to a 10b5-1 trading plan. Following the reported transaction, the filing shows 274,226 Class A shares beneficially owned directly and 149,294 held indirectly. The indirect holdings are attributable to three Drive Capital Overdrive funds with specific share counts disclosed in the footnote. The form is signed by an attorney-in-fact on behalf of the reporting person on 09/04/2025.

Amendment No. 11 to the Schedule 13D reports that Carvana Group, LLC and related reporting persons beneficially own an aggregate of 2,216,547 shares of Root, Inc. Class A common stock, representing approximately 14.0% of outstanding Class A shares (and ~12.5% on a fully-diluted, as-converted basis). The reported position includes 780,727 shares issuable upon conversion of Preferred Stock (14,053,096 preferred shares) and 1,435,820 shares issuable upon exercise of Exercisable Warrants. Short-term warrants expired September 1, 2025; one tranche of long-term warrants became exercisable September 1, 2025, with remaining warrants subject to milestone-based vesting and expirations through September 1, 2027. No other transactions in the prior 60 days were reported.

Root, Inc. (ROOT) filing a Form 144 notifies the market that 10,861 Class A shares will be offered for sale through Fidelity Brokerage Services on NASDAQ with an aggregate market value of $974,666.14. The shares were acquired by the seller on 04/01/2025 as restricted stock vesting and were granted as compensation. The filing also discloses a sale within the past three months: 8,290 Class A shares sold on 06/02/2025 for gross proceeds of $1,082,674.00. The filer represents compliance with Rule 144 and certifies no undisclosed material adverse information.

Root, Inc. (ROOT) insider sale notice: A holder intends to sell 5,750 Class A shares on the NASDAQ with an aggregate market value of $516,005 and lists approximately 13,618,876 Class A shares outstanding. The securities being offered were acquired through restricted stock vesting: 5,277 shares vested on 04/02/2024 and 473 shares vested on 05/01/2024, both received as compensation. The filer also disclosed a prior sale on 06/02/2025 of 5,256 Class A shares generating $686,433.60 in gross proceeds. The broker named for the proposed sale is Fidelity Brokerage Services LLC.

Drive Capital-related entities and Christopher Olsen filed an amended Schedule 13G reporting collective beneficial ownership of 307,732 shares of Root, Inc. Class A common stock, representing 2.3% of the outstanding Class A shares based on 13,618,876 shares outstanding. Ownership is held across multiple Delaware and Ohio entities: Drive Capital Overdrive Fund I, Drive Capital Overdrive Fund I (TE), Drive Capital Overdrive Ignition Fund I, Drive Capital Overdrive Fund I (GP), Drive Capital, DC I Investment, Purple Dot, and the Dwight H. Hibbard Family Trust. The filing details sole voting and dispositive power attributed to various entities and notes Christopher Olsen may be deemed to have voting and dispositive power through his roles. The document is an amendment executed and signed by Olsen on 08/14/2025.

Ribbit Capital and related entities disclosed beneficial ownership in Root, Inc.'s Class A common stock. Ribbit Capital IV, L.P. directly holds 503,800 Class A shares and 492,983 Class B shares, totaling 996,783 shares, reported as 7.1% on an equivalent Class A basis when conversion is assumed. RT-E Ribbit Opportunity IV, LLC holds 235,824 Class B shares, reported as 1.7%. Combined through Ribbit GP entities and Meyer Malka, the Reporting Persons are shown with aggregate beneficial ownership of 1,232,607 shares, or 8.7% of the Class A equivalent, based on 13.6 million Class A shares reported outstanding. The filing states each Class B share is convertible at the holder's option into one Class A share and that GP/UGP entities and Meyer Malka may be deemed to have sole voting and dispositive power over these shares. Bullfrog entities reported 0 shares.

Amendment No. 10 to Schedule 13D reports that Carvana-related reporting persons collectively hold beneficial interests equal to 7,952,386 shares of Root, Inc. Class A common stock, representing approximately 36.9% of outstanding Class A on the basis described in the filing. The reported position comprises 780,727 shares issuable on conversion of 14,053,096 shares of Preferred Stock and 7,171,659 shares issuable upon exercise of exercisable warrants directly held by Carvana Group, LLC.

The filing specifies the exercisable warrant tranches that underlie a portion of this stake: Tranche 1 (2,365,841 shares, $180 exercise), Tranche 2 (3,210,784 shares, $198 exercise) and Tranche 3 (1,595,034 shares, $216 exercise), with short-term warrants' exercise prices and expirations described and certain remaining tranches subject to milestone conditions. The filing also discloses conversion mechanics (Conversion Rate = Liquidation Preference / Conversion Price), that conversion/exercise prices were adjusted for a prior reverse split, and that the reporting persons report shared voting and dispositive power over the disclosed shares.