Christopher Olsen
Insider
First SEC filing: Oct. 27, 2020 · Latest: Oct. 27, 2020
Insider at
Insider transactions
0 buys (P)
0 sells (S)
Net: $0
Price change vs current quote, split-adjusted for corporate actions since the filing — not benchmarked, not annualized, not size-weighted
No open-market trades on record; showing all filings.
| Date | Ticker | Code | Shares | Price | Value | Owned after | Δ own | A/D | vs now |
|---|---|---|---|---|---|---|---|---|---|
| May 21, 2025 | ROOT | C | 1,443,376 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| May 21, 2025 | ROOT | J | 6,869 | · | · | 6,869 Indirect | · | Acquired | (price as of 2026-10-02) |
| May 21, 2025 | ROOT | J | 339,856 | · | · | 339,856 Indirect | · | Acquired | (price as of 2026-10-02) |
| May 21, 2025 | ROOT | J | 1,443,376 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| May 21, 2025 | ROOT | C | 1,443,376 | · | · | 1,443,376 Indirect | · | Acquired | (price as of 2026-10-02) |
| Aug. 31, 2022 | ROOT | C | 1,593 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Aug. 31, 2022 | ROOT | C | 54,382 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Aug. 31, 2022 | ROOT | C | 112,469 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Aug. 31, 2022 | ROOT | C | 1,593 | · | · | 1,593 Indirect | · | Acquired | (price as of 2026-10-02) |
| Aug. 31, 2022 | ROOT | C | 54,382 | · | · | 54,382 Indirect | · | Acquired | (price as of 2026-10-02) |
| Aug. 31, 2022 | ROOT | C | 112,469 | · | · | 112,469 Indirect | · | Acquired | (price as of 2026-10-02) |
| Nov. 23, 2021 | ROOT | C | 10,100,000 | · | · | 25,980,779 Indirect | -27.99% | Disposed | (price as of 2026-10-02) |
| Nov. 23, 2021 | ROOT | J | 10,100,000 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Nov. 23, 2021 | ROOT | C | 10,100,000 | · | · | 10,100,000 Indirect | · | Acquired | (price as of 2026-10-02) |
| Nov. 23, 2021 | ROOT | C | 10,100,000 | · | · | 25,980,779 Indirect | -27.99% | Disposed | (price as of 2026-10-02) |
| Nov. 23, 2021 | ROOT | J | 10,100,000 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Nov. 23, 2021 | ROOT | C | 10,100,000 | · | · | 10,100,000 Indirect | · | Acquired | (price as of 2026-10-02) |
| Nov. 19, 2021 | ROOT | D | 15,290 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| June 10, 2021 | ROOT | J | 5,117,841 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| June 10, 2021 | ROOT | J | 452,721 | · | · | 452,721 Indirect | · | Acquired | (price as of 2026-10-02) |
| June 8, 2021 | ROOT | A | 15,290 | · | · | 15,290 Direct | · | Acquired | (price as of 2026-10-02) |
| May 17, 2021 | ROOT | C | 5,117,841 | · | · | 46,060,569 Indirect | -10.00% | Disposed | (price as of 2026-10-02) |
| May 17, 2021 | ROOT | C | 5,117,841 | · | · | 5,117,841 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 28,683 | · | · | 28,683 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 978,891 | · | · | 978,891 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 2,024,456 | · | · | 2,024,456 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 51,178,410 | · | · | 51,178,410 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 28,683 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 978,891 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 2,024,456 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 12,178,320 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 10,447,860 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 13,602,870 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 14,949,360 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 28,683 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 978,891 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 2,024,456 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 51,178,410 | · | · | 0 Indirect | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 28,683 | · | · | 28,683 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 978,891 | · | · | 978,891 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 2,024,456 | · | · | 2,024,456 Indirect | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | C | 51,178,410 | · | · | 51,178,410 Indirect | · | Acquired | (price as of 2026-10-02) |
P = Open-market purchase · S = Sale · A = Grant/award · M = Option exercise · G = Gift · F = Tax withholding
Insider transactions are not a recommendation; sales are often driven by liquidity or tax reasons.
Derivative holdings (Form 4 Table II) Options, RSUs and convertible securities reported on Form 4 Table II.
| Date | Ticker | Security | Underlying | Exercise price | Expiration | Shares | A/D |
|---|---|---|---|---|---|---|---|
| May 21, 2025 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 1,443,376 | Disposed |
| Aug. 31, 2022 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 1,593 | Disposed |
| Aug. 31, 2022 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 54,382 | Disposed |
| Aug. 31, 2022 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 112,469 | Disposed |
| Nov. 23, 2021 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 10,100,000 | Disposed |
| Nov. 23, 2021 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 10,100,000 | Disposed |
| May 17, 2021 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 5,117,841 | Disposed |
| Oct. 30, 2020 | ROOT | Class B Common Stock [F10,F15] | Class A Common Stock | · | · | 28,683 | Acquired |
| Oct. 30, 2020 | ROOT | Class B Common Stock [F10,F15] | Class A Common Stock | · | · | 978,891 | Acquired |
| Oct. 30, 2020 | ROOT | Class B Common Stock [F10,F15] | Class A Common Stock | · | · | 2,024,456 | Acquired |
| Oct. 30, 2020 | ROOT | Class B Common Stock [F10,F15] | Class A Common Stock | · | · | 51,178,410 | Acquired |
| Oct. 30, 2020 | ROOT | Series E Preferred Stock [F6] | Common Stock | · | · | 28,683 | Disposed |
| Oct. 30, 2020 | ROOT | Series E Preferred Stock [F6] | Common Stock | · | · | 978,891 | Disposed |
| Oct. 30, 2020 | ROOT | Series E Preferred Stock [F6] | Common Stock | · | · | 2,024,456 | Disposed |
| Oct. 30, 2020 | ROOT | Series B Preferred Stock [F4] | Common Stock | · | · | 12,178,320 | Disposed |
| Oct. 30, 2020 | ROOT | Series A-3 Preferred Stock [F3] | Common Stock | · | · | 10,447,860 | Disposed |
| Oct. 30, 2020 | ROOT | Series A-2 Preferred Stock [F2] | Common Stock | · | · | 13,602,870 | Disposed |
| Oct. 30, 2020 | ROOT | Series A-1 Preferred Stock [F1] | Common Stock | · | · | 14,949,360 | Disposed |
Exercise/conversion price is blank when not applicable (e.g. RSUs).
Initial ownership (Form 3) 7 holdings
Securities held when first becoming an insider, per SEC Form 3.
| Date | Ticker | Security | Shares | Ownership |
|---|---|---|---|---|
| Oct. 27, 2020 | ROOT | Series A-1 Preferred Stock | 14,949,360 | Indirect |
| Oct. 27, 2020 | ROOT | Series A-2 Preferred Stock | 13,602,870 | Indirect |
| Oct. 27, 2020 | ROOT | Series A-3 Preferred Stock | 10,447,860 | Indirect |
| Oct. 27, 2020 | ROOT | Series B Preferred Stock | 12,178,320 | Indirect |
| Oct. 27, 2020 | ROOT | Series E Preferred Stock | 2,024,456 | Indirect |
| Oct. 27, 2020 | ROOT | Series E Preferred Stock | 978,891 | Indirect |
| Oct. 27, 2020 | ROOT | Series E Preferred Stock | 28,683 | Indirect |