Doug Ulman
Insider
First SEC filing: Oct. 27, 2020 · Latest: June 4, 2026
Insider at
Insider transactions
0 buys (P)
1 sells (S)
Net: $-593,287
Price change vs current quote, split-adjusted for corporate actions since the filing — not benchmarked, not annualized, not size-weighted
| Date | Ticker | Code | Shares | Price | Value | Owned after | Δ own | A/D | vs now |
|---|---|---|---|---|---|---|---|---|---|
| June 3, 2026 | ROOT | A | 2,864 | · | · | 3,983 Direct | +255.94% | Acquired | (price as of 2026-10-02) |
| March 9, 2026 | ROOT | C | 33,352 | · | · | 40,672 Direct | +455.63% | Acquired | (price as of 2026-10-02) |
| March 9, 2026 | ROOT | F | 473 | $45.77 | $21,649 | 40,199 Direct | -1.16% | Disposed | 1.1% (price as of 2026-10-02) |
| March 9, 2026 | ROOT | S | 13,152 | $45.11 | $593,287 | 27,047 Direct | -32.72% | Disposed | 2.5% (price as of 2026-10-02) |
| March 9, 2026 | ROOT | M | 33,352 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| March 9, 2026 | ROOT | M | 33,352 | $0.65 | $21,679 | 33,352 Direct | · | Acquired | 7016.9% (price as of 2026-10-02) |
| March 9, 2026 | ROOT | C | 33,352 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| Dec. 1, 2025 | ROOT | G | 2,505 | · | · | 7,896 Indirect | -24.08% | Disposed | (price as of 2026-10-02) |
| June 4, 2025 | ROOT | A | 1,119 | · | · | 7,320 Direct | +18.05% | Acquired | (price as of 2026-10-02) |
| March 24, 2025 | ROOT | C | 2,000 | · | · | 8,201 Direct | +32.25% | Acquired | (price as of 2026-10-02) |
| March 24, 2025 | ROOT | S 10b5-1 | 2,000 | $175.00 | $350,000 | 6,201 Direct | -24.39% | Disposed | -73.6% (price as of 2026-10-02) |
| March 24, 2025 | ROOT | M | 2,000 | · | · | 33,352 Direct | -5.66% | Disposed | (price as of 2026-10-02) |
| March 24, 2025 | ROOT | M | 2,000 | $0.65 | $1,300 | 2,000 Direct | · | Acquired | 7016.9% (price as of 2026-10-02) |
| March 24, 2025 | ROOT | C | 2,000 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| March 13, 2025 | ROOT | C | 4,000 | · | · | 10,201 Direct | +64.51% | Acquired | (price as of 2026-10-02) |
| March 13, 2025 | ROOT | S 10b5-1 | 4,000 | $138.53 | $554,120 | 6,201 Direct | -39.21% | Disposed | -66.6% (price as of 2026-10-02) |
| March 13, 2025 | ROOT | M | 4,000 | · | · | 35,352 Direct | -10.16% | Disposed | (price as of 2026-10-02) |
| March 13, 2025 | ROOT | M | 4,000 | $0.65 | $2,600 | 4,000 Direct | · | Acquired | 7016.9% (price as of 2026-10-02) |
| March 13, 2025 | ROOT | C | 4,000 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| Dec. 12, 2024 | ROOT | G | 1,250 | · | · | 6,201 Direct | -16.78% | Disposed | (price as of 2026-10-02) |
| June 5, 2024 | ROOT | A | 2,305 | · | · | 17,852 Direct | +14.83% | Acquired | (price as of 2026-10-02) |
| Aug. 16, 2023 | ROOT | A | 7,792 | · | · | 15,547 Direct | +100.48% | Acquired | (price as of 2026-10-02) |
| June 7, 2022 | ROOT | A | 115,207 | · | · | 139,609 Direct | +472.12% | Acquired | (price as of 2026-10-02) |
| April 12, 2022 | ROOT | G | 172,911 | · | · | 172,911 Indirect | · | Acquired | (price as of 2026-10-02) |
| April 12, 2022 | ROOT | G | 172,911 | · | · | 24,402 Direct | -87.63% | Disposed | (price as of 2026-10-02) |
| June 30, 2021 | ROOT | A | 9,112 | · | · | 197,313 Direct | +4.84% | Acquired | (price as of 2026-10-02) |
| June 14, 2021 | ROOT | C | 172,911 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| June 14, 2021 | ROOT | C | 172,911 | · | · | 188,201 Direct | +1130.88% | Acquired | (price as of 2026-10-02) |
| June 8, 2021 | ROOT | A | 15,290 | · | · | 15,290 Direct | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 172,911 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 708,340 | · | · | 708,340 Direct | · | Acquired | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 708,340 | · | · | 0 Direct | -100.00% | Disposed | (price as of 2026-10-02) |
| Oct. 30, 2020 | ROOT | J | 172,911 | · | · | 172,911 Direct | · | 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 |
|---|---|---|---|---|---|---|---|
| March 9, 2026 | ROOT | Stock Option (Right to Buy) | Class B Common Stock | $0.65 | Jan. 17, 2027 | 33,352 | Disposed |
| March 9, 2026 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 33,352 | Acquired |
| March 9, 2026 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 33,352 | Disposed |
| March 24, 2025 | ROOT | Stock Option (Right to Buy) | Class B Common Stock | $0.65 | Jan. 17, 2027 | 2,000 | Disposed |
| March 24, 2025 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 2,000 | Acquired |
| March 24, 2025 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 2,000 | Disposed |
| March 13, 2025 | ROOT | Stock Option (Right to Buy) | Class B Common Stock | $0.65 | Jan. 17, 2027 | 4,000 | Disposed |
| March 13, 2025 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 4,000 | Acquired |
| March 13, 2025 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 4,000 | Disposed |
| June 14, 2021 | ROOT | Class B Common Stock | Class A Common Stock | · | · | 172,911 | Disposed |
| Oct. 30, 2020 | ROOT | Stock Option (Right to Buy) | Class B Common Stock [F1,F2] | $0.04 | Jan. 17, 2027 | 708,340 | Acquired |
| Oct. 30, 2020 | ROOT | Stock Option (Right to Buy) | Common Stock [F1] | $0.04 | Jan. 17, 2027 | 708,340 | Disposed |
| Oct. 30, 2020 | ROOT | Class B Common Stock [F1,F2] | Class A Common Stock | · | · | 172,911 | Acquired |
Exercise/conversion price is blank when not applicable (e.g. RSUs).
Initial ownership (Form 3) 2 holdings
Securities held when first becoming an insider, per SEC Form 3.