Clemes Benjamin Michael

CEO buys 5,754 shares of ROLR at $2.53; 2 other insiders also bought within 14 days; stock down -68.0% from 52-week high.

Clemes Benjamin Michael (CEO) purchased 5,754 shares at $2.53 on 2025-08-19, increasing his holdings to 160,607 shares. The transaction coincides with a cluster pattern: 2 other insiders also bought within the past 14 days. However, the company's fundamentals are concerning—it recorded a net income of $-592,000.00 in its latest quarter and was unprofitable over its most recent full fiscal year, while annual revenue contracted -6.0%. The stock is down -68.0% from its 52-week high, trading at a current price of $2.54. Reviewing the CEO's same-ticker history at ROLR, only 2 of his 5 prior purchases resulted in positive 90-day returns; his cross-ticker track record shows an average 90-day return of -21.5% across all holdings. The cluster buy pattern merits attention given the company's negative profitability and revenue decline, though without earnings catalysts or material announcements in the FACTS, the reasons for the coordinated purchases remain unclear.

CEO Clemes bought 2,500 shares of ROLR at $2.12 on 2025-05-22; stock down -69.3% from 52-week high.

CEO Benjamin Michael Clemes purchased 2,500 shares at $2.12, adding 1.6% to his holdings of 154.9K shares. This purchase occurs in a context of significant weakness: the stock trades at $2.44, down -69.3% from its 52-week high of $7.94 and -21.3% over the past 30 days. At the company level, High Roller Technologies posted revenue of $6.8M in its latest quarter against a net loss of $-3.3M, with full-year net income negative and annual revenue declining -6.0% year-over-year. Clemes's prior trades at ROLR have not materialized as gains: of 3 prior buys with measurable 90-day outcomes, all showed negative returns (ranging from -24.5% to -52.9%), with a 0% win rate at the 90-day mark. This purchase also coincides with a cluster pattern: 3 other insiders bought within the same 14-day window, which warrants observation but does not indicate coordinated strategy absent additional evidence.

CEO Clemes Benjamin Michael bought 5,000 shares at $2.34 on 2025-05-19; stock down 74.7% from 52-week high, company unprofitable with -6.0% annual revenue growth.

Clemes Benjamin Michael, CEO, purchased 5,000 shares at $2.34, bringing his holdings to 152,353 shares. The purchase follows a pattern of repeated share acquisitions at High Roller Technologies—he has made 4 prior purchases since October 2024, with none achieving positive returns at the 90-day mark (0 of 3 prior buys were well-timed). His cross-ticker track record across all open-market buys shows an average 90-day return of -44.4% with a 0% win rate, reflecting a consistent pattern of unfavorable timing. The company is materially constrained: most recent quarter revenue of $6,771,000.00 reflects -6.0% annual revenue growth, and the firm posted net income of $-3,276,000.00 and was unprofitable over its most recent full fiscal year. At current price $2.01, the stock has declined -74.7% from its 52-week high of $7.94 and -26.9% over the past 30 days. A cluster of 2 other insiders also bought within the past 14 days, though this represents concurrent activity rather than validation of timing or fundamental outlook.

CEO Clemes Benjamin Michael bought 4,000 shares of ROLR at $3.14 on 2025-03-25; stock now -54.7% from 52-week high despite cluster buy from 3 other insiders.

Clemes Benjamin Michael, CEO, purchased 4,000 shares at $3.14, bringing his holdings to 147,353 shares. The transaction occurs in a deteriorating price environment: the stock is -54.7% from its 52-week high and has declined -5.5% over the past 30 days and -15.9% over 90 days. His prior trades at this ticker show a consistent pattern of poor timing, with all 3 prior buys delivering negative 90-day returns (-45.3%, -33.8%, -24.5%), and his cross-ticker track record shows average 90-day returns of -44.4% with a 0% win rate. The company reported negative net income of $-501,000.00 and annual revenue decline of -6.0%, indicating financial stress. While a cluster of 3 other insiders also bought within the past 14 days, the CEO's personal history of persistently ill-timed purchases at this ticker and the company's deteriorating fundamentals raise questions about transaction rationale separate from the broader insider activity pattern.

CEO Clemes Benjamin Michael bought 4,000 shares in 2 purchases ($6.16, $6.80) for $25,920.00 total, raising stake to 65,353 shares.

Clemes Benjamin Michael, Chief Executive Officer, executed 2 separate purchases totaling 4,000 shares for $25,920.00 between December 6–9, 2024, at prices of $6.16 and $6.80 with a blended average of $6.48. His post-transaction holdings of 65,353 shares represent a 6.5% increase from prior holdings of 61,353 shares. The current price of $6.65 sits 16.2% below the 52-week high of $7.94 but 11.2% above its 30-day average, placing the buys in a recovery context. Notably, his prior open-market purchase at ROLR on 2024-10-23 showed a 30-day loss of 24.5%, and across his cross-ticker track record, his prior buy averaged a negative 30-day return of 24.5%, establishing a pattern of timing challenges in recent transactions. The company's latest quarterly results show revenue of $7,516,000.00 and a net loss of $501,000.00, with market cap at $54,976,215.00, indicating a profitable executive buying into a struggling microcap.

CEO Clemes Benjamin Michael bought 6,250 shares at $8.00 on 2024-10-23; cluster buy pattern with 4 other insiders in 14 days.

CEO Clemes Benjamin Michael purchased 6,250 shares for $50,000.00, increasing his holdings from 55,103 shares to 61,353 shares (+11.3% vs pre-transaction holdings). The transaction occurred at $8.00 per share just three days before the current price of $7.75, indicating a modest price decline post-purchase. The significance is amplified by a cluster pattern: 4 other insiders also bought within the past 14 days, suggesting coordinated or mutually-reinforced conviction across the leadership team at a newly listed company. This synchronized activity across multiple executives warrants investor scrutiny of the company's strategic positioning and near-term operational outlook.