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Proprietary & Confidential Information Not for Further Dissemination March 3, 2025
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Proprietary & Confidential Information Not for Further Dissemination This is a “Safe Harbor” Statement under the Private Securities Litigation Reform Act of 1995. Any forward-looking statements contained herein, including statements related to our outlook for the industry and for our performance for the year 2025 and beyond, are based upon the Company’s historical performance and on current plans, estimates and expectations. The inclusion of this forward-looking information should not be regarded as a representation by us or any other person that the future plans, estimates or expectations contemplated by us will be achieved. They are subject to various risks and uncertainties, including but not limited to: the cyclical nature of the property casualty industry; the impact of significant competition, including new entrants to the industry; the long-tail and potentially volatile nature of the insurance and reinsurance business; product demand and pricing; claims development and the process of estimating reserves; investment risks, including those of our portfolio of fixed maturity securities and investments in equity securities, including investments in financial institutions, municipal bonds, mortgage-backed securities, loans receivable, investment funds, including real estate, merger arbitrage, energy related and private equity investments; the effects of emerging claim and coverage issues; the uncertain nature of damage the ories and loss amounts, including claims for cyber security-related risks; natural and man-made catastrophic losses, including as a result of terrorist activities; the ongoing effects of the COVID-19 pandemic, or other epidemics and pandemics; the impact of climate change, which may alter the frequency and increase the severity of catastrophe events; general economic and market activities, including inflation, interest rates, and volatility in the credit and capital markets; the impact of the conditions in the financial markets and the global economy, and the potential effect of legislative, regulatory, accounting or other initiatives taken in response to such conditions, on our results and financial condition; foreign currency and political risks relating to our international operations; our ability to attract and retain key personnel and qualified employees; continued availability of capital and financing; the success of our new ventures or acquisitions and the availability of other opportunities; the availability of reinsurance; our retention under the Terrorism Risk Insurance Program Reauthorization Act of 2019; the ability or willingness of our reinsurers to pay reinsurance recoverables owed to us; other legislative and regulatory developments, including those related to business practices in the insurance industry; credi t risk related to our policyholders, independent agents and brokers; changes in the ratings assigned to us or our insurance company subsidiaries by rating agencies; the availability of dividends from our insurance company subsidiaries; cyber security breaches of our information technology systems and the information technology systems of our vendors and other third parties, or related processes and systems; the effectiveness of our controls to ensure compliance with guidelines, policies and legal and regulatory standards; and other risks detailed from time to time in the Company’s filings with the Securities and Exchange Commission. These risks and uncertainties could cause our actual results for the year 2025 and beyond to differ materially from those expressed in any forward- looking statement we make. Any projections of growth in our revenues would not necessarily result in commensurate levels of earnings. Forward- looking statements speak only as of the date on which they are made, and the Company undertakes no obligation to update publi cly or revise any forward-looking statement, whether as a result of new information, future developments or otherwise. 2 FORWARD-LOOKING INFORMATION
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Proprietary & Confidential Information Not for Further Dissemination 3 COMPETITIVE ADVANTAGES Knowledge and Expertise Decentralization Focus on Long Term Risk-Adjusted Return UNIQUE COMPETITIVE ADVANTAGES DRIVE SUSTAINABLE GROWTH AND PROFITABILITY Industry Product Geography Close to Customer Specialized Expertise Speed in Responding to Changing Market Conditions Cycle Management Exposure and Volatility Management Total Investment Return Superior Long-Term Risk-Adjusted Return on Equity and Shareholder Value Creation
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Proprietary & Confidential Information Not for Further Dissemination4 DELIVERING BEST IN CLASS ROEs AND GROWTH IN NET INCOME 0.00% 5.00% 10.00% 15.00% 20.00% 25.00% RETURN ON BEGINNING EQUITY $0 $200 $400 $600 $800 $1,000 $1,200 $1,400 $1,600 $1,800 $2,000 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 NET INCOME
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Proprietary & Confidential Information Not for Further Dissemination5 DELIVERING ON SUCCESSFUL LONG-TERM STRATEGY AS A DECENTRALIZED SPECIALIST UNDERWRITER $0 $2 $4 $6 $8 $10 $12 $14 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 $ Billions NET PREMIUMS WRITTEN 20% 25% 30% 35% 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 IMPROVING EXPENSE RATIO 0% 10% 20% 30% 40% 50% 60% 70% 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 CONSISTENT LOSS RATIO Average 62.0% $0 $200 $400 $600 $800 $1,000 $1,200 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 $ Millions UNDERWRITING INCOME
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Proprietary & Confidential Information Not for Further Dissemination6 MANAGING THE INSURANCE CYCLE FOR LONG-TERM SUCCESS High Profitability Price Reductions Low Profitability Reduced Competition Price Increases WRB: Write as much good business as possible WRB: Be willing to sacrifice volume for profitability WRB: Focus on retention; maintain disciplined underwriting WRB: Slower growth and more selective underwriting WRB: Capitalize on market dislocations Create new units/divisions to position for market turn WRB: Accelerate growth as price adequacy returns to various market segments Lines of business no longer move in lockstep * * * * * * * Workers’ Compensation * D&O * Property * Other Liability * Commercial Auto *Casualty Re Increased Competition
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Proprietary & Confidential Information Not for Further Dissemination7 DECENTRALIZATION FACILITATES GROWTH IN PARTS OF BUSINESS WITH BEST MARGIN POTENTIAL Certain lines of business have been reclassified to conform to current presentation 32% 15% 18% 12% 10% 8% 2% 3% 2020 $7.3B NPW Other liability Workers' compensation Short-tail lines Auto Professional liability Casualty reinsurance Monoline excess Property reinsurance 36% 10% 20% 13% 9% 6% 4% 2% 2024 $12.0B NPW Other liability Workers' compensation Short-tail lines Auto Professional liability Casualty reinsurance Monoline excess Property reinsurance 64.8% Growth
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Proprietary & Confidential Information Not for Further Dissemination8 E&S AND SPECIALTY MARKETS CONTINUE TO PROVIDE AMPLE OPPORTUNITIES 0% 2% 4% 6% 8% 10% 12% 14% 2000 2005 2010 2015 2020 % of P/C DPW Hundreds Surplus Lines % of Total P/C DPW Source: AM Best data and research Increases in E&S as a percentage of total DPW in hard markets have demonstrated staying power Unprecedented growth in the specialty insurance segment over the past few years is forecast to continue over the next several years U.S. SPECIALTY INSURANCE MARKET 10 YEAR 10.6% CAGR Source: Deloitte, Turbocharging the specialty insurance market, April 2024 126.8% 84.5% 0% 20% 40% 60% 80% 100% 120% 140% 2018 2019 2020 2021 2022 2023 2024 WRB CUMULATIVE GPW GROWTH SINCE 2018 Admitted Non-Admitted Total -10% -5% 0% 5% 10% 15% 20% 25% 30% 35% 4Q19 1Q20 2Q20 3Q20 4Q20 1Q21 2Q21 3Q21 4Q21 1Q22 2Q22 3Q22 4Q22 1Q23 2Q23 3Q23 4Q23 1Q24 2Q24 3Q24 4Q24 Jan-25 Quarterly Industry E&S Premium Growth Aggregate CA, FL, TX Stamping Office Data
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Proprietary & Confidential Information Not for Further Dissemination QUARTERLY RATE CHANGE 2018-2024 9 75% CUMULATIVE ANNUAL RATE INCREASE EXCLUDING WORKERS’ COMPENSATION SINCE YE 2017 74.8% 0.0% 10.0% 20.0% 30.0% 40.0% 50.0% 60.0% 70.0% 80.0% 2017 2018 2019 2020 2021 2022 2023 2024 CUMULATIVE ANNUAL RATE INCREASE EXCLUDING WORKERS’ COMPENSATION SINCE 2017 Quarter Rate Increase Excluding Workers’ Compensation Quarter Rate Increase Excluding Workers’ Compensation Q1 2018 5.0% Q3 2021 10.0% Q2 2018 3.1% Q4 2021 9.3% Q3 2018 3.9% Q1 2022 8.7% Q4 2018 3.9% Q2 2022 7.5% Q1 2019 6.2% Q3 2022 7.4% Q2 2019 5.4% Q4 2022 6.9% Q3 2019 7.0% Q1 2023 8.3% Q4 2019 8.8% Q2 2023 8.2% Q1 2020 11.9% Q3 2023 8.5% Q2 2020 12.9% Q4 2023 8.0% Q3 2020 14.2% Q1 2024 7.8% Q4 2020 15.2% Q2 2024 8.3% Q1 2021 12.9% Q3 2024 8.4% Q2 2021 9.6% Q4 2024 7.9%
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Proprietary & Confidential Information Not for Further Dissemination 9.6% 6.9% 10.9% 13.8% 16.2% 3.0% 4.3% 11.4% 3.9% 5.0% 3.8% 5.4% 3.6% 4.3% 1.1% 2.4% 0.9% 0.0% 1.7% 0.9% 1.9% 0.8% 2.8% 1.1% 1.4% 1.5% 0% 2% 4% 6% 8% 10% 12% 14% 16% 18% 6/30/1992 Hurricane Andrew 12/31/1993 Northridge Earthquake 6/30/2001 Sept. 11 Attacks 6/30/2005 Hurricane Katrina Financial Crisis as of 3/31/2009(1) 3/31/2011 2Q11 Storms 9/30/2012 Storm Sandy 6/30/2017 3Q2017 Events 9/30/2018 4Q2018 Events 12/31/2019 COVID-19 2020 (2) 6/30/2021 Hurricane Ida (3) 6/30/2022 Hurricane Ian (4) 6/30/24 Hurricanes Helene & Milton (5) Industry Event Loss/Surplus WRB Event Loss/Surplus SIGNIFICANTLY LESS VOLATILITY FROM CATASTROPHES 10 RATIO OF EVENT LOSS TO SURPLUS FOR LARGEST EVENTS SINCE 1992* * Ratio is for end-of-quarter surplus immediately prior to event. (1) Change in surplus from 12/31/2007 peak to date of maximum capital erosion at 3/31/09. Reflects losses offset by earnings. (2) Howden estimate > $44B (3) Swiss Re industry estimate $30-32B. WRB includes all 3Q21 catastrophe losses. (4) Aon industry estimate $50-55B. WRB includes all 3Q22 catastrophe losses. (5) Gallagher Re 2025 Natural Catastrophe Report Sources: PCS; Insurance Information Institute; A.M. Best; WRB
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Proprietary & Confidential Information Not for Further Dissemination Average 20-year Standard Deviation = 7.6 Loss Ratio Points SIGNIFICANTLY LESS VOLATILITY OVERALL 11 Source: S&P Capital IQ Pro 0.0 2.0 4.0 6.0 8.0 10.0 12.0 14.0 16.0 405060708090 Standard Deviation of Loss Ratio over 20 Years (In Loss Ratio Points) 20-Year Average Loss Ratio Higher Volatility, Worse Loss Ratio Average 20-year Average Loss Ratio = 61.4% WRB Lower Volatility, Better Loss Ratio Higher Volatility, Better Loss Ratio Lower Volatility, Worse Loss Ratio 2004-2023
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Proprietary & Confidential Information Not for Further Dissemination QUARTERLY RESERVE REVIEW PROCESS Peer reviewed by Corporate actuary - independent work and view Senior executive review Annual Third-party independent review Full reserve analysis completed by- line at each business 12 COMPETITIVE ADVANTAGES: LOWER EARNINGS VOLATILITY ▪ Results in frequent small movements that reduce the likelihood of large periodic adjustments ▪ Reduces systemic reserving risk within the enterprise ▪ Provides greater accuracy and accountability BETTER POSITIONING ▪ Frequency and granularity allow us quickly to see and react to trends in both reserving and underwriting ▪ Creates a real-time feed back loop between reserving and business decision makers, which facilitates better pricing and risk selection REFLECTS LONG-TERM VIEW ROBUST QUARTERLY RESERVE PROCESS MINIMIZES VOLATILITY AND POSITIONS BUSINESS FOR FUTURE PROFITABILITY
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Proprietary & Confidential Information Not for Further Dissemination13 FIRST MENTION First mentioned potentially early signs of an uptick in activity amongst the plaintiff bar on 2Q16 earnings call 2016 ISSUE RECOGNITION Began increasing reserves for long-tailed liability lines and IBNR % of NPE based on early indications Rate increases began in earnest 2018 PROACTIVE MEASURES Began adding an “X-factor” to observed loss trend for the uncertainty of future social inflation 2019 CYCLE MANAGEMENT Leveraged decentralized structure to lean into areas with best profit opportunity while deemphasizing others as lines of business ceased to move in lockstep 2022 TARGETING EXCESS Took further action on excess and umbrella business to lower limits and increase attachment points, as well as reduce participations in larger towers 2023 MANAGING SOCIAL INFLATION UNDERWRITING ACTION In addition to significant rate increases in excess of loss costs, tightened terms and conditions and increased use of non-admitted paper. Focus on insurance to value 2020 CLOSURE Performed claims reviews at select businesses. Many large excess and umbrella business claims settled or reserved to limits. 2024 HOLDING THE LINE Maintained Ex-Cat AYLR despite investment community preference for companies who “did the math” and lowered it based on rate increases 2021
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Proprietary & Confidential Information Not for Further Dissemination14 IMPROVEMENT IN KEY LOSS RESERVE METRICS 30.0% 35.0% 40.0% 45.0% Accident Year At 12 Months INITIAL IBNR AS A PERCENT OF NET PREMIUMS EARNED 30.0% 35.0% 40.0% 45.0% 50.0% 55.0% 60.0% Calendar Year PAID LOSS RATIO 48.0% 50.0% 52.0% 54.0% 56.0% 58.0% 60.0% 62.0% Calendar Year IBNR % OF TOTAL RESERVES 1.00 1.10 1.20 1.30 1.40 1.50 1.60 1.70 Calendar Year IBNR / CASE RESERVES
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Proprietary & Confidential Information Not for Further Dissemination15 RESERVE RISK HAS DECLINED AS CARRIED RESERVE POSITION HAS IMPROVED TO 69TH PERCENTILE OF ACTUARIAL RANGE Carried Reserves @12/31/2024 $17.14B 69th PERCENTILE Carried Reserves @ 12/31/2019 $10.76B 53rd PERCENTILE 53% 69% 0 1 0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 100%
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Proprietary & Confidential Information Not for Further Dissemination16 INVESTMENT INCOME CONTINUES TO BENEFIT FROM INCREASING INVESTED ASSETS AND HIGHER INTEREST RATES $0 $500 $1,000 $1,500 $2,000 $2,500 $3,000 $3,500 $4,000 2018 2019 2020 2021 2022 2023 2024 CASH FLOW FROM OPERATIONS($000) $11,000 $13,000 $15,000 $17,000 $19,000 $21,000 $23,000 2018 2019 2020 2021 2022 2023 2024 INVESTMENTS IN FIXED MATURITY SECURITIES At December 31 ($000) 0.0% 1.0% 2.0% 3.0% 4.0% 5.0% 6.0% $0 $300 $600 $900 $1,200 $1,500 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 Yield % Investment Income ($ Million) INVESTMENT INCOME Fixed Maturity Non-Fixed Maturity Average Annualized Yield on Fixed Maturity IMPLICATIONS OF FED MOVES ▪ New money rates remain higher than the roll-off from the existing portfolio ▪ Since the Fed cut, the rest of the yield curve has moved up modestly ▪ The Federal deficit, combined with Treasury supply and declining foreign demand, may put upward pressure on the long end of the yield curve ▪ Our short duration provides the opportunity to extend if yield curve continues to move to be more normal and positively shaped
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Proprietary & Confidential Information Not for Further Dissemination $ Millions Growth in Net Premiums Earned 5.0% 7.5% 10.0% 12.5% 15.0% New Money Rate 4.50% 10.4% 12.0% 13.7% 15.4% 17.0% 4.75% 11.0% 12.7% 14.4% 16.0% 18.0% 5.00% 11.7% 13.4% 15.0% 16.7% 18.4% 5.25% 12.3% 14.0% 15.7% 17.4% 19.1% 5.50% 13.0% 14.7% 16.4% 18.1% 20.1% $192 $222 $253 $284 $315 $204 $234 $265 $296 $327 $215 $246 $278 $309 $340 $227 $259 $290 $321 $352 $239 $271 $302 $333 $365 17 GROWTH IN NET INCOME SENSITIVITY (%) Represents % increase over annualized 9-month 2024 net income adjusted for additional income from Argentine Inflation –linked securities. Dollar figures represent incremental pretax income annualized 9-month 2024 pretax income adjusted for additional income from Argentine inflation-linked securities. Incremental investment income based on estimated 12 -month cash flow, roll-off investments and related income received reinvested at New Money Rate for 12 months Assumes constant combined ratio of 90.3% Tax Rate = 21% Not a projection. For illustrative purposes only.
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Proprietary & Confidential Information Not for Further Dissemination 1973 1976 1979 1982 1985 1988 1991 1994 1997 2000 2003 2006 2009 2012 2015 2018 2021 2024 Note: W. R. Berkley Corporation’s book value per share has been adjusted for stock dividends paid from 1975 to 1983. Stock dividends were 6% in each year from 1975 to 1978, 14% in 1979, and 7% in each year from 1980 to 1983. The Company has paid cash dividends each year since 1975. 5,929% W. R. Berkley Corporation S&P 500 ® RELATIVE STOCK PRICE PERFORMANCE W. R. Berkley Corporation vs. S&P 500® Cumulative Growth: 65,735% LONG-TERM VALUE CREATION 18 OVERALL GAIN IN BOOK VALUE PER SHARE WITH DIVIDENDS COMPOUNDED W. R. Berkley Corporation vs. S&P 500® 122,151% % 25,000% 50,000% 75,000% 100,000% 125,000% 1973 1976 1979 1982 1985 1988 1991 1994 1997 2000 2003 2006 2009 2012 2015 2018 2021 2024
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203-629-3040 www.berkley.com “Always do right. This will gratify some people, and astonish the rest.” - Mark Twain - Karen Horvath khorvath@wrberkley.com