Darryl Rawlings is CEO & President at TRUPANION, INC. (TRUP). They have made 146 open-market trades across 1 company since 2015, most recently 2026-08-22.
CIK 0001611679
Unrated. We grade insiders only on stock they chose to buy on the open market. Grants, option exercises and vesting say nothing about timing, so they don't count — which is why someone can file often and still have no grade. It isn't a bad sign: unrated buys beat every graded tier below A.
1 open-market purchase totalling $500K since 2024, against 145 sales. Too few scored purchases to measure a record yet.
| Ticker | Shares | Value |
|---|---|---|
| TRUP | 25,151 | $706K |
Shares reported on the most recent Form 4, priced at the 2026-08-26 close.
| Ticker | Type | Traded | Filed | Price | Value | 7d Stock | 30d Stock | 90d Stock |
|---|---|---|---|---|---|---|---|---|
| TRUP | SELL | 2025-09-03 | 2025-09-05 | $44.74 | $4.5M | +2.4% | -4.5% | -15.9% |
| TRUP | BUY | 2024-05-07 | 2024-05-15 | $24.14 | $500K | -13.6% | -18.0% | +26.4% |
| TRUP | SELL · 10b5-1 | 2023-05-08 | 2023-05-10 | $25.30 | $101K | +2.2% | +7.7% | +40.8% |
| TRUP | SELL · 10b5-1 | 2023-04-19 | 2023-04-20 | $35.48 | $142K | +2.8% | -28.7% | -18.5% |
| TRUP | SELL · 10b5-1 | 2023-04-04 | 2023-04-06 | $41.20 | $165K | -12.2% | -37.3% | -46.0% |
| TRUP | SELL · 10b5-1 | 2023-03-16 | 2023-03-20 | $55.17 | $221K | -30.4% | -39.4% | -54.9% |
| TRUP | SELL | 2023-02-28 | 2023-02-28 | $58.10 | $232K | -13.7% | -30.7% | -64.1% |
| TRUP | SELL | 2023-02-13 | 2023-02-15 | $58.50 | $234K | -1.2% | -8.0% | -66.5% |
| TRUP | SELL | 2023-01-26 | 2023-01-30 | $54.33 | $217K | +3.3% | +4.0% | -33.3% |
| TRUP | SELL | 2023-01-09 | 2023-01-11 | $48.54 | $194K | +0.8% | +5.2% | -18.7% |
| TRUP | SELL | 2022-12-23 | 2022-12-28 | $48.96 | $196K | +7.4% | +21.2% | -20.4% |
| TRUP | SELL | 2022-12-07 | 2022-12-09 | $51.03 | $204K | +2.2% | -7.7% | +4.2% |
| TRUP | SELL | 2022-11-18 | 2022-11-22 | $60.41 | $242K | +1.6% | -0.9% | +3.1% |
| TRUP | SELL | 2022-11-03 | 2022-11-07 | $44.16 | $177K | +29.0% | +9.4% | +30.5% |
| TRUP | SELL | 2022-10-17 | 2022-10-19 | $53.94 | $216K | -1.0% | +6.4% | +9.8% |
| TRUP | SELL | 2022-09-30 | 2022-10-19 | $61.38 | $246K | -1.0% | +6.4% | +9.8% |
| TRUP | SELL | 2022-09-14 | 2022-09-16 | $65.57 | $262K | -0.5% | -14.8% | -21.7% |
| TRUP | SELL | 2022-08-29 | 2022-09-01 | $69.34 | $277K | -3.1% | -13.2% | -23.4% |
| TRUP | SELL | 2022-08-10 | 2022-10-19 | $66.86 | $267K | -1.0% | +6.4% | +9.8% |
| TRUP | SELL | 2022-08-08 | 2022-08-11 | $66.86 | $267K | -7.7% | -3.2% | -37.7% |
| TRUP | SELL | 2022-07-26 | 2022-07-28 | $64.21 | $514K | +3.1% | +10.3% | -19.5% |
| TRUP | SELL | 2022-07-07 | 2022-07-11 | $66.11 | $264K | +13.2% | +14.4% | -18.0% |
| TRUP | SELL | 2022-06-21 | 2022-06-24 | $53.10 | $212K | +7.1% | +4.4% | -7.1% |
| TRUP | SELL | 2022-06-02 | 2022-06-06 | $66.52 | $266K | -22.0% | -3.7% | -2.1% |
| TRUP | SELL | 2022-05-17 | 2022-05-19 | $64.90 | $519K | +1.9% | -15.7% | +9.4% |
Grouped by shared companies and similar filing behaviour. This is a similarity measure, not a ranking or a performance signal.