March 2022 Investor Presentation

Compelling financial metrics Business model designed to reduce earnings volatility Growth & underwriting outlooks improving Prudent capital management Management and BoD have significant skin in the game . VALUE PROPOSITION Currently trading at significant discount to peers, despite attractive relative ROE and income metrics • Consistent track record of book value growth Vertically integrated structure provides a hedge in catastrophe years, reducing loss retention and further reducing earnings volatility, supporting use of P/E-based valuation for HRTG • Solid reinsurance program, including lowest reinsurance retention in FL peer group as a % of equity; protects against hurricanes and other severe events, reducing earnings volatility • Organic premium growth, fueled by relationships with independent agents and auto carriers Diversification initiatives and recent re-underwriting and de-risking efforts should benefit underwriting margins Commercial residential business serves as an AoB-hedge in Florida and provides us with additional growth opportunities Investment grade debt rating provides easy access to capital, allowing nimble response to market opportunities as they arise Below-peer operating leverage = ample capital to fuel our growth • Track record of capital return via share repurchases and regular dividend . Successful M&A execution provides synergies and access to new markets Significant insider ownership aligns management's and BoD's interests with shareholders Total insider ownership = 9% of outstanding shares March 2022 Investor Presentation 15 H

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