#1HCI Investor Presentation NYSE: HCI | NOVEMBER 2023#2Forward-Looking Statement This presentation includes certain forward-looking statements and information, including statements regarding plans, strategies and expectations of HCI Group, Inc. ("HCI" or the "Company"). When used in this presentation, words such as "believes," "anticipates," "expects," "estimates," or words of similar meaning are generally intended to identify forward-looking statements. All statements other than statements of historical fact included in this presentation are forward-looking statements. These forward-looking statements are subject to risks, uncertainties, assumptions and other factors, many of which are beyond the control of the Company. Important factors that could cause actual results to differ materially from those expressed or implied by the forward-looking statements are described in the Company's filings it makes from time to time with the Securities and Exchange Commission, including within the "Risk Factors" section of the Annual Report on Form 10-K for the year ended December 31, 2022, filed March 10, 2023. HCI 1#3Property & Casualty Insurance Stock Price2 $75.70 Est. Market Capitalization² $650M Insurance Technology Book Value/Share $23.27 Dividend Yield² 2.1% In-Force Premium $773M Debt to Capital³ 51% HCI at a Glance Reinsurance (1) All data as of 9/30/2023 except where noted (2) As of 11/10/23 (3) Excludes preferreds securities HCI Founded/IPO Management Tenure 2006/2008 13 years Real Estate Insider Ownership 21% 2#4Investment Thesis An insurance holding company with operations in Homeowners Insurance, Information Technology Services, Reinsurance, and Real Estate HCI 2006 founded Combining technology and industry knowledge to drive profitable growth 59/64 profitable quarters Allocating capital with purpose and discipline while managing risk Creating value for our shareholders 52 consecutive quarters of dividends 12% 21% TEN-YEAR ROE1 INSIDER OWNERSHIP >$420M capital returned to shareholders since (1) As of 12/31/2022 (2) Includes $269M buybacks and $155M dividends HCI inception² 3#5Growing Through Investment & Innovation CITIZENS PROPERTY INSURANCE CORPORATION Executed first Citizens assumption GREENLEAF CAPITAL, LLC Launched real estate division TypTap Launched Typ Tap insurance business UIHCA HCI transitions polices in 4 Northeast states from UIHC ANCHOR INSURANCE HCI transitions all policies from Anchor Insurance TypTap Typ Tap insurance group raises $100M in capital UIHC HCI agrees to transition policies in 3 Southeast states from UIHC Gulfstream Property & Casualty Insurance HOMEOWNERS CHOICE Incorporated Homeowners Choice in Florida О CLADDAUGH Formed captive reinsurance division Completed initial public offering О EXZEO Started information technology division Home Introduced Typ Tap Homeowners product ○ HCI transitions business from Gulfstream P&C HCI HCI Group premium in force exceeds $700 million TypTap Typ Tap approved in 20 states О 2006 2007 2008 2011 2012 2016 2018 2020 2021 2022 HCI 4#6Overview of HCI Business Divisions HOMEOWNERS CHOICE TypTap CLADDAUGH PROPERTY & CASUALTY INSURANCE TECHNOLOGY REINSURANCE GREENLEAF CAPITAL, LLC REAL ESTATE Homeowners and condominium insurance primarily in Florida Track record of consistent underwriting profitability Strong cash flow helps to fund growth initiatives Growth fueled by opportunistic acquisitions $423M of In-Force Premiums (1) Technology-driven homeowners insurance Nationwide expansion announced in 2020 Differentiated technology yields best-in-class loss ratio $350M of In-Force Premiums (1) Reinsurance captive that participates in the placement of reinsurance for HCI's insurance divisions Licensed Class 3 Bermuda reinsurer Selectively retain margin from our reinsurance tower Provides Reinsurance Flexibility Real estate company with significant investments in Florida Opportunistic strategy focused on maximizing long-term value Returns enhanced by efficient capital allocation and in-house expertise >$100M Real Estate Portfolio (1) (1) As of 9/30/2023 HCI 5#7A Growing Homeowners Business Two Carriers in 13 States With Over $730M (1) in Annual Premium HCI Premium in Force (in $M) HCI Loss Ratio 2 $528 $353 $369 $338 $773 $719 $737 41% 2017 2018 2019 2020 2021 2022 3Q23 32% 3Q22 3Q23 Premium growth... ...with profitability (1) Trailing twelve-months gross premiums earned (2) Losses and loss adjustment expenses divided by gross premiums earned. Loss ratios excludes Hurricane lan losses in 3Q 2022 and Hurricane Idalia losses in 3Q 2023. 00 6#8HOMEOWNERS CHOICE Property & Casualty Insurance#9Florida Focused Insurance Business with Strong Operating Performance Homeowners Choice In-Force Premiums (in $M) $482 $422 $423 $377 $323 $309 2018 2019 2020 2021 Best-in-class Underwriter in the Florida Market Opportunistically Acquiring Profitable Books of Business 2022 3Q23 Proactively Managing Risk and Loss Costs (1) The decline in in-force premium from 2021 to 2022 reflects the transition of business assumed from United Property & Casualty Insurance Company to TypTap Insurance Company. HOMEOWNERS CHOICE Deploying Excess Capital Into Investments & Growth Initiatives 8#10Customer Centric Model Delivers High Customer Retention Strict underwriting, exposure management, and industry-leading claims technology support risk selection, customer retention and loss control >70% (2) of in-force premium retained more than 6 years and counting Average non-cat gross loss ratio below 40% % OF IN-FORCE PREMIUM (1) Anchor Property & Casualty, Gulfstream Property & Casualty, and United Property & Casualty books transitioned in 2020 and 2021 (2) As of 9/30/22 HOMEOWNERS CHOICE High Retention of In-Force Premium Includes Anchor, Gulfstream, and UPC1 26% 74% POLICY <6 YEARS OLD POLICY 6 YEARS AND OLDER 9#11Value-Added Portfolio Acquisitions DECEMBER 2021 HCI Has acquired UIHCA Georgia, North Carolina & South Carolina personal insurance lines AUGUST 2021 HCI Has selected policies of Gulfstream Property & Casualty Insurance ~$300M of in-force premiums acquired for $12M, resulting in earnings accretion Florida insurance policies $87 million of $3.1 million cash annual premiums consideration $25 million of annual premiums $0 upfront consideration Thoughtful acquisition strategy drives profitable growth DECEMBER 2020 HCI Has acquired UIHCA Connecticut, New Jersey, Massachusetts & Rhode Island personal insurance lines $112 million of $5.4 million equity annual premiums consideration APRIL 2020 HCI Has acquired ANCHOR INSURANCE Florida insurance policies $62 million of $3 million cash annual premiums consideration Financial strength and integration capabilities make HCI a preferred acquisition partner Underwriting algorithms and proprietary use of data allows for improved profitability of acquired portfolios HOMEOWNERS CHOICE 10 10#12TypTap Insurance Insurance Technology Bay-19 232333 8324.155 4324 ALL 10:00 Nov-13 STOP#13U.S. Homeowners Insurance is a Massive Opportunity... ...with Attractive Features Homeowners market is large and growing Fragmented with one company > 10% share High average premium and strong retention Incumbents under-investing in technology Opportunity to capture market share $130B Total U.S. market in 2022 Strong customer retention is leading to a subscription-like business model TypTap 12#14TypTap Insurance Technology-Driven Insurance Company Proprietary Technology National Expansion Superior Underwriting Positive Cash Flow Experienced Management 13#15We Use Technology to Underwrite at the Individual Property Level 72% 1 industry average loss ratio TypTap's Differentiated Strategy Individual property level risk evaluation Only write insurance for homes that are expected to be profitable on a standalone basis over the life of the policy Optimizing for profitable growth Source: S&P Market Intelligence (U.S. homeowners insurance industry direct expenses). Excludes reinsurance expense (1) Represents industry average from 2014-2022 TypTap ~25 point decrease in loss ratio Up to 1000 Data Points per Property Individual Property Level Risk Selection Trained Algorithms Track Record of Profitable Underwriting 14#16Individual Level Risk Evaluation Results in TypTap's Lower Loss Ratio > RED PROPERTIES (not approved): Risks that we expect to be unprofitable and will not bind GREEN PROPERTIES (approved): Those that meet our return thresholds based on our underwriting algorithm TypTap Nassau Dr Nassau Dr Alhambra Blvd Biltmore Blvd Blvd 7350 embassy blvd. Property level (Typ Tap) vs. zip code level (industry) TypTap's algorithms can determine "green properties" vs. "red properties" in the same neighborhood Fairway Blvd Island Dr 15#17HCI Developed its Own Technology Exzeo Was Launched in 2012 to Build and Develop TypTap's Entire Technology Stack EXZEO Exzeo founded atlasviewer Launched Atlas Viewer ClaimColony Launched Casaclue and Claim Colony casacue property dossier Started writing flood policies after 4 years of development HARMONY National EXZEO Wholly-owned technology subsidiary A team of over 150 experienced developers and data scientists 100% internally developed technology platform powers every aspect of TypTap's and HCI's day-to-day operations Launched Harmony Launched homeowners refined Al engine expansion 2012 2014 2015 2016 2017 2018 2021 TypTap 16#18Exzeo's Full-stack Tech Platforms Power Typ Tap Simplified Customer Experience... Powered by a Full Suite Solution Intuitive agent interface Enter an address to start a quote, and then answer 4-8 simple questions Intelligent data repository Casaclue, our intelligent data repository, provides the rest of the information needed to complete the quote Real time decisions The information is fed to the Underwriting, Cost and Rating Engines to determine if it is a red or green property Frictionless, automated quote & bind All this is done with no Typ Tap human intervention JUSTEZ Field adjuster management HARMONY Quoting & policy administration 100% Internally Developed O CASACLUE Intelligent data repository TypTap CLAIM COLONY Claims management ATLASVIEWER Mapping & data visualization 17#19Our Data Repository is Curated for Precise Risk Evaluation Data sourced through in-house proprietary research and 3rd party resources Curated and validated data delivered to decision algorithms Information continuously accumulates, creating a perpetual evolution of data IIR Satellite imaging to identify homes with pool cages, which can increase claim and replacement costs considerably Satellite imaging to determine proportion of 'hip' v. 'gable' roofs¹ 1 In Hip roofs, all sides slope downward over the walls of the home; in Gable roofs, there are two sides or peaks that slope downward over the walls of the home Source: Oliver Wyman analysis (from discussions with TypTap management and expert interviews). TypTap High resolution lidar maps and geospatial coordinates to build an accurate elevation dataset Text mining of public litigation history - 18#20Algorithms Transforming Data Into Profit The curated data is fed into our underwriting, cost rating engines Algorithm-enabled engines determine red or green properties Historical trends are applied to underwriting and costs to refine and improve the risk selection algorithms Underwriting algorithms are customized per state Typ Tap uses data to refine & update algorithms How much weight to assign each one Typ Tap has a multi-year track record of improving and refining risk evaluation TypTap Which data points are predictive Which characteristics are reliable 19#21Increased conversion of selected risks through attractive pricing Better underwriting results and profit Typ Tap delivers value for agents and consumers Ability to selectively underwrite best risks TypTap VALUE PROPOSITION Investment in technology Increased "first looks" at Typ Tap policies Ease of use for agents 20 20#22Why Typ Tap Partners with Agents We partner with agents because that's where most policies are written Overwhelming majority of homeowners insurance is bought through the independent agent channel Independent agent model allows us to scale and we do not have to change consumer behavior for our growth plan Direct Written Premium by Distribution Channel 93% The predictability of our customer acquisition cost ("CAC") improves the efficiency to utilize our capital for growth At the same time, we built our technology platform to be distribution agnostic TypTap Agents Source: McKinsey & Company (2020 report) Over 90% of policies still sold through agents 7% Direct 21 21#23Purpose-built technology suite 100% owned by Typ Tap TypTap's Advantages Differentiated data and proprietary analytics creating superior underwriting results Aggregation of profitable properties is enhanced by high customer retention rate TypTap® Ease of use for a frictionless policyholder and agent experience 22 22#24TypTap's Geographic Footprint Current footprint¹ (1) Typ Tap is approved to offer homeowners coverage in 20 states, including Florida. Typ Tap is currently operating in 13 states. TypTap Expanding footprint through nationwide licensing effort 23#25Typ Tap is Operating to Maximize Growth AND Profitability Typ Tap Gross Written Premium (in $M) Typ Tap CAGR: 121% (vs. 7.5% for U.S. homeowners insurance industry)1 $247M $15M $60M $105M $348M $342M 2018 2019 2020 2021 2022 3Q23 LTM Typ Tap Insurance Group Loss Ratio² 48% 39% 3Q22 (1) Direct Premium Written from 2018 - 2022 (2) Losses and loss adjustment expenses divided by gross premiums earned. Loss ratios excludes Hurricane lan losses in 3Q 2022 and Hurricane Idalia losses in 3Q 2023. ТурТар 3Q23 24 24#26CLADDAUGH Reinsurance 25#27Claddaugh Generating Profits for Our Shareholders $160 $140 $120 $100 $80 $60 $40 $20 $0 Cumulative Net Premium Earned Since 2008 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (1) As of 12/31/22. Excludes the impact of intercompany stop loss agreement. CLADDAUGH Claddaugh is used to opportunistically manage reinsurance cycles for HCI's insurance divisions. $ Since its formation in 2008, Claddaugh has contributed $36M in pre-tax income to HCI. 26 26#28GREENLEAF CAPITAL Real Estate 27#29Creating Value in Real Estate Acquire properties with unique value drivers Greenleaf Capital owns and operates HCI's growing real estate portfolio. Its holdings. include a set of premier commercial assets in rapidly growing Florida. Reinvest or harvest GREENLEAF CAPITAL, LLC Optimize capital structure Develop or reposition 28#30Generating Gains from our Real Estate Portfolio Recent Sales Transactions PROPERTY Office Building LOCATION Downtown Tampa DATE PURCHASED GROSS PROCEEDS2 PRE-TAX GAIN 1 2010 $44M $37M Office Building Downtown Tampa 2017 $15M $13M Grocery Anchored Retail Eustis, FL 2016 $13M $5M Grocery Anchored Retail Melbourne, FL 2016 $18M $11M (1) Includes gains associated with bargain purchase (2) Gross proceeds are net of transaction costs and commissions GREENLEAF CAPITAL, LLC $90M $66M GROSS PROCEEDS PRE-TAX GAIN 29 29#31Florida Real Estate Portfolio With Embedded Value UNDER OPERATING DEVELOPMENT PROPERTY Office Portfolio Anchored Retail APPRAISED VALUE (1) BOOK VALUE (3) DEBT ON PROPERTY $25M $18M $4M 28M 17M $12M Waterfront Specialty Use Portfolio 40M 17M Land Under Development (1) Based on appraisals obtained by Fifth Third bank. As of 9/30/2023 (2) Book value is net of depreciation (3) All data as of 9/30/2023 GREENLEAF CAPITAL, LLC 21M 13M $114M1 APPRAISED VALUE $66M BOOK VALUE 30#32Homeowners Choice Investment Portfolio A conservative allocation, positioned for higher rates and opportunistic investments Total invested assets1 $293 million Fixed Income Average 2 Duration 1 year (1) As of 9/30/23 HCI 13% 2% 10% ■ Cash Fixed Income ■Real Estate & Other HOMEOWNERS CHOICE ■ Short Term Investments 75% ■ Equity Limited Partnerships 31#33Typ Tap Investment Portfolio A conservative allocation, positioned for higher rates and opportunistic investments Total invested assets 1 $230 million Fixed Income Average Duration 1 year (1) As of 9/30/23 HCI 12% 1% ■ Cash TypTap 86% Fixed Income ■Real Estate & Other ■ Short Term Investments ■ Equity Limited Partnerships 32#34Experienced & Focused Leadership Team HCI PARESH PATEL Chairman & Chief Executive Officer ☐ Founder; Chairman since 2007 & CEO since 2011 Designed HCI's policy administration systems, leveraging software development experience ■ Founded NorthStar Bank in 2004 and served as Director (2006-2011) MARK HARMSWORTH Chief Financial Officer, HCI Group CFO since 2017; previously SVP of Finance Former senior advisor to Stewart Information Services (NYSE: STC) CFO of First American Title Insurance Company (2006-2011) Senior EVP of First Canadian Title Insurance Company (2002-2006) KARIN COLEMAN President, Homeowners Choice Chief Operating Officer, HCI Group ■ Director since February 2021 Previously, EVP (2017-2019) and VP of Corp. Services (2009-2017) Former VP Strategic Alliances, TSIC, Inc. (2001-2009) Served in various capacities at Florida Progress Corp (NYSE: FPC), a utility holding company, now part of Duke Energy (NYSE: DUK) (1987-2000) ANDREW GRAHAM General Counsel, HCI Group General Counsel since 2008 Served in various capacities, including General Counsel for Trinsic (1999-2007) Served on Internal Audit Committee of Hillsborough County, Florida, since 2011 Hillsborough Community College trustee (2007-2011) KEVIN MITCHELL President, Typ Tap Insurance Executive Vice President, Typ Tap Insurance Group Previously, SVP and VP of Investor Relations (2013-2019) ■ Former Area Director of Financial Institutions practice at Arthur J. Gallagher (NYSE: AJG) (2008-2013) Previously, employed by Oswald Companies, one of the nation's largest independent insurance brokerage firms (2005-2008) ANTHONY SARAVANOS President, Greenleaf Capital Director since 2007; President of Greenleaf Capital since 2013 ■ Former VP of full-service real estate firm in Palm Harbor, Florida (2005-2013) Managing Partner of 13 commercial CRE entities in Florida and New York since 2001 Director of First Home Bank since 2011; Chairman since 2015 333#35Delivering Shareholder Value HCI capital returned to >$420M shareholders since inception² 21% HOMEOWNERS CHOICE TypTap inside ownership CLADDAUGH GREENLEAF CAPITAL, LLC 12% ROE1 10-year average >1600% Total Shareholder Return since IPO 1) As of December 31, 2022 2) Includes $269M buybacks and $155M dividends HCI 34 =4#36HCI Contact Us INVESTOR RELATIONS CONTACT Matt Glover Gateway Group, Inc. Tel (949) 574-3860 [email protected] HCI GROUP, INC. 3802 Coconut Palm Drive Tampa, FL 33619 Tel (813) 849-9500 www.hcigroup.com [email protected] 35 55