High Roller Technologies's three largest insider shareholders as of September 29, 2026 are Invest Ab Oeh (TenPercentOwner, 2.64Mn shares), Holdings Ltd Cascadia (Director, 1.80Mn shares), Seth Adam Young (Chief Executive Officer, 208.30K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Invest Ab Oeh | TenPercentOwner | 2,638,395 | 0 | 2,638,395 | 50.7% | 25 Oct, 2024 |
| 2 | Holdings Ltd Cascadia | Director | 1,800,748 | 0 | 1,800,748 | 34.6% | 26 May, 2026 |
| 3 | Seth Adam Young | Chief Executive Officer | 208,296 | 0 | 208,296 | 4.0% | 24 Mar, 2026 |
| 4 | Benjamin Michael Clemes | Chief Executive Officer | 160,607 | 0 | 160,607 | 3.1% | 20 Aug, 2025 |
| 5 | Adam Jonathan Felman | Chief Financial Officer | 157,425 | 0 | 157,425 | 3.0% | 21 Aug, 2026 |
| 6 | Brandon Christopher Eachus | Director, TenPercentOwner | 89,968 | 0 | 89,968 | 1.7% | 20 Aug, 2025 |
| 7 | Matthew Evan Teinert | Chief Financial Officer | 57,000 | 0 | 57,000 | 1.1% | 26 Dec, 2024 |
| 8 | Michael Cribari | Director, TenPercentOwner | 46,052 | 0 | 46,052 | 0.9% | 10 Jun, 2025 |
| 9 | Daniel Waldemar Bradtke | Director | 29,979 | 0 | 29,979 | 0.6% | 21 Sep, 2026 |
| 10 | John Milton Iv Francis | Chief Operating Officer | 15,022 | 0 | 15,022 | 0.3% | 17 Mar, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 17 Sep, 2026 | Daniel Waldemar Bradtke | Director | Disposed S | 5,000 | $6.16 | $30.80K | 29,979 | Direct |
| 19 Aug, 2026 | Adam Jonathan Felman | Chief Financial Officer | Disposed S | 3,600 | $5.42 | $19.51K | 157,425 | Direct |
| 28 Apr, 2026 | Holdings Ltd Cascadia | Director | Disposed J | 787,648 | — | — | 1,800,748 | Direct |
| 19 May, 2026 | Brandon Christopher Eachus | Director, TenPercentOwner | Acquired A | 15,000 | $0.00 | $0 | 15,000 | Direct |
| 19 May, 2026 | Kristen Gayle Britt | Director | Acquired A | 15,000 | $0.00 | $0 | 15,000 | Direct |
| 19 May, 2026 | Michael Cribari | Director, TenPercentOwner | Acquired A | 15,000 | $0.00 | $0 | 15,000 | Direct |
| 19 May, 2026 | Daniel Waldemar Bradtke | Director | Acquired A | 15,000 | $0.00 | $0 | 15,000 | Direct |
| 19 May, 2026 | Iv David Weild | Director | Acquired A | 15,000 | $0.00 | $0 | 15,000 | Direct |
| 19 May, 2026 | Jonas Fredrik Martensson | Director | Acquired A | 15,000 | $0.00 | $0 | 15,000 | Direct |
| 17 May, 2026 | Adam Jonathan Felman | Chief Financial Officer | Disposed F | 3,525 | $0.00 | $0 | 161,025 | Direct |
| 20 Mar, 2026 | Seth Adam Young | Chief Executive Officer | Acquired A | 120,500 | $0.00 | $0 | 208,296 | Direct |
| 20 Mar, 2026 | Adam Jonathan Felman | Chief Financial Officer | Acquired A | 100,000 | $0.00 | $0 | 164,550 | Direct |
| 13 Mar, 2026 | John Milton Iv Francis | Chief Operating Officer | Acquired P | 2,277 | $3.95 | $8.99K | 15,022 | Direct |
| 08 Jan, 2026 | John Milton Iv Francis | Chief Operating Officer | Acquired A | 10,000 | $0.00 | $0 | 12,745 | Direct |
| 08 Jan, 2026 | John Milton Iv Francis | Chief Operating Officer | Acquired A | 75,000 | $0.00 | $0 | 75,000 | Direct |
| 19 Dec, 2025 | Adam Jonathan Felman | Chief Financial Officer | Acquired P | 9,500 | $1.36 | $12.92K | 64,550 | Direct |
| 08 Dec, 2025 | John Milton Iv Francis | Chief Operating Officer | Acquired P | 1,424 | $1.76 | $2.51K | 1,424 | Direct |
| 09 Dec, 2025 | John Milton Iv Francis | Chief Operating Officer | Acquired P | 1,321 | $1.89 | $2.50K | 2,745 | Direct |
| 04 Dec, 2025 | Seth Adam Young | Chief Executive Officer | Acquired P | 5,850 | $1.58 | $9.24K | 12,796 | Direct |
| 17 Nov, 2025 | Seth Adam Young | Chief Executive Officer | Acquired P | 3,091 | $2.42 | $7.48K | 5,346 | Direct |