Hagerty, Inc.: Insider Activity and Valuation Crossroads

Hagerty, Inc. (NYSE: HGTY), a global leader in vehicle insurance and media services, has recently drawn attention due to significant insider selling activity disclosed in SEC filings. This raises critical questions about near-term valuation opportunities amid mixed signals from corporate insiders and institutional investors. Let us dissect the data to assess whether the stock presents a compelling investment case or a risk-laden proposition.

The Insider Selling Conundrum

The most notable transactions stem from Robert I. Kauffman, a director and 10% shareholder, who executed three major sales of Class A Common Stock in late June 2025. On June 20, he sold 7,747 shares at $9.82, followed by 11,710 shares at $10.02 on June 23, and 31,110 shares at $10.14 on June 24. Cumulatively, this reduced his holdings via Aldel LLC from 3.8 million to 3.74 million shares, a 1.6% decline over four days.

Crucially, these sales were executed under a Rule 10b5-1 trading plan established in August 2024. Such plans allow insiders to pre-schedule trades without needing to react to market conditions, often to diversify holdings or meet financial obligations. While this mitigates concerns about “insider pessimism,” the sheer volume—over 67,000 shares in a week—could spook short-term traders, especially if perceived as a liquidity move.

A Counterbalancing Signal: The Informative Buy

Not all insider activity is bearish. Anthony J. Kuczinski, another director, demonstrated confidence by purchasing 28,630 shares at $9.44–$9.75 on May 14, 2025. This $286,000 direct purchase signals a positive outlook, contrasting Kauffman's prearranged sales. Kuczinski's transaction, classified as “informative,” suggests he views the stock as undervalued at current levels.

Institutional Dynamics and Valuation Metrics

Institutional investors hold 20.51% of Hagerty's stock, with recent adjustments by funds like KLP Kapitalforvaltning and Ancora Advisors. The stock's $9.86 price as of June 24 sits below its 200-day moving average of $9.61, but above the 50-day average of $9.34, indicating short-term resilience.

Financially, Hagerty reported Q1 2025 EPS of $0.08, beating estimates, with revenue rising to $319.59 million. Analysts project annual EPS of $0.22, which, if achieved, would imply a P/E ratio of 49.28—a premium to peers. This high valuation hinges on sustained growth in its core insurance and media segments.

The Crossroads: Risk vs. Reward

The mixed signals from insiders underscore a valuation crossroads. On one hand, Kauffman's sales—though pre-arranged—may reflect a strategic rebalancing of his portfolio, especially given Hagerty's high P/E. On the other, Kuczinski's buy and the company's strong Q1 results suggest fundamentals remain robust.

The stock's $3.37 billion market cap and institutional ownership indicate it is a mid-cap play with limited speculative overhang. However, the revocation of its Municipal Advisor registration (though non-core) adds regulatory uncertainty.

Investment Considerations

• Bull Case: If Hagerty's media arm (Hagerty Media) continues to expand its subscription base and event offerings, and insurance margins stabilize, the stock could rise to $12–$13, aligning with its 52-week highs.
• Bear Case: A slowdown in vehicle insurance demand or regulatory headwinds could push the stock toward its 2023 lows of $8.03.

Conclusion: A Hold with Cautious Optimism

Hagerty's near-term trajectory is ambivalent. While institutional support and Kuczinski's buy provide a floor, the high valuation and Kauffman's selling create a ceiling. Investors should monitor the stock's performance against the $9.61–$10.00 range as a key technical indicator.

For now, a hold rating seems prudent. Aggressive investors might consider a small position if the stock dips below $9.00, leveraging the Q1 earnings beat and Kuczinski's bullish stance. However, the elevated P/E demands flawless execution—any misstep could trigger a sharp correction.

In the Hagerty story, the interplay of insider behavior and valuation metrics will be the key to unlocking the next phase of returns. Stay alert, but remain disciplined.