PRHI Conifer Holdings, Inc. Insider Trading

Director Smith James Grant buys 24,772 shares at blended average $0.74 for $18,397.28

Director Smith James Grant executed 2 separate purchases totaling 24,772 shares (24.8K shares) for $18,397.28 at an average price of $0.74 per share on April 6 and April 13, 2026, increasing his stake by 68.5% from 36,150 shares to 60,922 shares post-transaction. The purchases occurred while the stock is trading at $4.13, which is 67.9% below its 52-week high of $12.88, and come amid deteriorating fundamentals: the company reported negative net income of $-3,970,000.00 ($-4.0M) in the latest quarter and full-year net income was negative, with annual revenue declining 35.6% year-over-year. His cross-ticker track record shows 2 prior open-market buys with an average 90-day return of +9.9% and a 100.00% win rate, though this historical performance cannot be assumed to predict outcomes at this specific ticker where he has not established a measurable buy-and-hold track record.

CEO Brian Roney buys 100,000 shares of PRHI at $0.72; stock -35.6% YoY revenue, -$4.0M net income

CEO Brian Roney purchased 100,000 shares (100.0K shares) at $0.72 on 2026-04-01, raising his holdings by 24.4% to 510,232 shares (510.2K shares). The transaction occurs amid material operational headwinds: annual revenue contracted -35.6% and the company reported a full-year net loss of $3,970,000.00 ($-4.0M). The stock currently trades at $5.40, representing a -58.1% decline from its 52-week high of $12.88, though it has recovered +15.1% over the prior 30 days. The scale of the CEO's buy—representing a significant addition to his personal stake during a period of revenue collapse and operating losses—stands in contrast to the company's deteriorating financial position and should prompt examination of his stated rationale and confidence horizon.

10% owner Clarkston Companies acquires 9,066,960 shares ($17.1M) across 2 transactions; stock down 63.6% from 52-week high amid revenue decline.

Clarkston Companies, a 10% stakeholder, executed 2 separate purchases totaling 9,066,960 shares for $17,065,360.00 at a blended average price of $1.88 per share. The first purchase involved 1,600 shares at $5,000.00 on 2025-12-23, followed by a significantly larger acquisition of 9,065,360 shares at $1.00 on 2026-02-27. This activity occurs as the company's stock trades at $4.69, down 63.6% from its 52-week high of $12.88 and down 26.0% over the past 90 days. Presurance Holdings faces material operational headwinds: annual revenue declined 31.9% year-over-year with the latest quarter showing only $6,679,000.00 in revenue against a net loss of $3,970,000.00. The substantial dollar commitment by an existing major shareholder warrants examination of whether this reflects a belief in turnaround potential or responses to specific company developments not disclosed in the filing.

Director Hakala acquires 101,500 shares at blended $75.86 vs current $0.81, 3 separate purchases totaling $7.7M across 3 months.

Hakala Jeffrey Anthony, a Director at Conifer Holdings, executed 3 separate purchases totaling 101,500 shares for $7,700,000.00 over a three-month period (December 2024 through March 2025). His prior buy at this ticker on 2023-12-20 declined 100.0% by both the 30-day and 90-day marks, establishing a pattern of poor timing outcomes at CNFR. The current stock price of $0.81 now trades 56.4% below the 52-week high and reflects a dramatic collapse from his transaction prices, which ranged from $2.00 to $5,000.00 per share. Conifer's fundamentals show deteriorating performance: annual revenue declined 31.9% year-over-year, and the blended transaction price of $75.86 far exceeds current valuation context, suggesting a severe and sustained disconnect between the purchase valuations and current market reality.

10% Owner Clarkston Ventures buys 100,000 shares of CNFR at $2.00; stock now trades at $0.81, down 56.4% from 52-week high.

Clarkston Ventures purchased 100,000 shares at $2.00 per share on 2024-12-12, increasing its holdings from 3,635,769 shares to 3,735,769 shares. The transaction occurred at a significant premium to the current price of $0.81, suggesting either the purchase was made when the stock traded higher or market conditions have deteriorated materially since the transaction date. The company's financial backdrop is mixed: revenue declined 31.9% year-over-year, and the stock is down 56.4% from its 52-week high of $1.86, though it trades at an exceptionally low P/E of 0.33 with a market cap of $9,900,533.61. The 10% owner's continued accumulation despite recent price weakness and revenue contraction warrants examination of the timing and motivation behind the purchase relative to when the transaction was executed and what has occurred in the interim.

10% owner Clarkston 91 West LLC bought 500 shares of CNFR at $5,000.00 total ($2.5M), raising stake 50% amid revenue decline.

Clarkston 91 West LLC, a 10% owner, purchased 500 shares for $2,500,000.00 on 2025-03-03, increasing holdings from 1,000 shares to 1,500 shares (+50.0%). This substantial investment occurs as CNFR faces significant headwinds: annual revenue growth is -31.9%, and the stock trades at $0.81, down 56.4% from its 52-week high of $1.86. The transaction price of $5,000.00 per share far exceeds the current market price of $0.81, suggesting either a private placement at a premium valuation or a structured transaction distinct from open-market trading. The company maintains positive fundamentals with net income of $2,051,000.00 on quarterly revenue of $16,134,000.00, but the sharp revenue contraction and steep mark-down from transaction price to current market price warrant careful scrutiny of the transaction structure and underlying company dynamics.

10% Owner Hakala purchases 101,500 shares across 3 transactions totaling $7,700,000.00 at blended average $75.86; stock now trades at $0.81.

Hakala Gerald W, a 10% owner of Conifer Holdings, executed 3 separate purchases totaling 101,500 shares for $7,700,000.00 between December 2024 and March 2025, with transaction prices ranging from $2.00 to $5,000.00 per share and a blended average price of $75.86. The current stock price of $0.81 is dramatically below the blended average purchase price, representing a massive unrealized loss on the aggregate position. Hakala's cross-ticker track record shows 1 prior buy with an average 90-day return of -100.0%, and his single prior purchase at CNFR (2023-12-20) also posted a 90-day return of -100.0%, meaning the prior buy was entirely underwater by the 90-day mark. The company's fundamentals show revenue contraction of -31.9% year-over-year with a P/E of 0.33 and market cap of $9,900,533.61, indicating significant operational and valuation stress. This filing merits scrutiny for the extreme disparity between historical purchase prices and current market levels, combined with the insider's poor historical timing across both this ticker and other securities.

Director Smith James Grant bought 20,150 shares of CNFR at $0.67 on 2025-04-10; holdings up 125.9%; cluster of 2 other insiders buying.

Director Smith James Grant purchased 20,150 shares at $0.67 on 2025-04-10, increasing his holdings from 16,000 to 36,150 shares—a 125.9% increase. This transaction occurs as part of a cluster pattern, with 2 other insiders also buying within the past 14 days, suggesting coordinated accumulation at a company whose stock has declined 44.6% over 90 days and trades at only 66.7% below its 52-week high. The timing is notable given the sharp recent weakness: the insider's prior buy at this ticker occurred just one day earlier (2025-04-09), and the company reports an extraordinary P/E of 0.09 alongside net income of $52,788,000.00 against revenue of only $16,017,000.00—a financially anomalous profile that merits scrutiny. The stock is currently $0.05 below the purchase price, and annual revenue has contracted 31.9% year-over-year, leaving open questions about earnings quality and sustainability.

Director Smith James Grant bought 16,000 shares of CNFR at $0.68; stock down 63.4% from 52-week high with cluster buy pattern underway

Smith James Grant, a director at Conifer Holdings, purchased 16,000 shares at $0.68 on 2025-04-09, establishing a new position. The stock is trading 63.4% below its 52-week high of $1.86 and has declined 19.0% over the past 30 days and 39.3% over the past 90 days. The company's fundamentals show significant deterioration: annual revenue declined 31.9% year-over-year, and while the latest quarter posted $16.0M in revenue and $52.8M in net income, the stock trades at a P/E of 0.10 with a market cap of $8.3M. This purchase occurs within a cluster pattern, as 2 other insiders also bought within the past 14 days. The convergence of depressed price action, material revenue contraction, and coordinated insider buying within a two-week window warrants close observation to determine whether the cluster represents informed conviction or coincidental timing.

Director SARAFA JOSEPH D bought 100,000 shares of CNFR at $0.53 (+40.0% increase in holdings)

SARAFA JOSEPH D purchased 100,000 shares at $0.53 on 2025-04-07, expanding his stake from 250,000 to 350,000 shares (+40.0%). The transaction occurred while the stock was trading at $0.60 (current), down -67.7% from its 52-week high of $1.86 and down -35.4% over the prior 30 days. The company reports a P/E of 0.09 and positive net income of $52.8M on quarterly revenue of $16.0M, but annual revenue growth shows -31.9% contraction year-over-year. This purchase by a director at a depressed price level—substantially below the 52-week range—occurs amid deteriorating revenue trajectory and significant recent price weakness, creating tension between the fundamentals (profitable, low valuation multiple) and the operational trend (declining sales). Investors should examine whether the purchase reflects confidence in stabilization or an opportunistic accumulation at a marked-down price amid operational headwinds.