Here are 1-2 brief analogies for White Mountains Insurance (WTM):

• A Berkshire Hathaway of specialty insurance.
• An IAC for insurance companies and programs.

Major Products/Services of White Mountains Insurance (WTM)

• Specialty Insurance and Reinsurance: Provides various niche insurance coverages and reinsurance protection for other insurers through its subsidiary Ark Insurance Holdings.
• Municipal Bond Insurance: Guarantees scheduled principal and interest payments for bonds issued by U.S. states, cities, and other local governments through Build America Mutual (BAM).
• Capital Solutions for Asset Managers: Offers permanent capital solutions to independent asset management firms, often taking minority equity stakes, through its subsidiary Kudu Investment Management.

White Mountains Insurance (WTM) operates as an insurance holding company with a diversified portfolio of businesses. While its subsidiaries serve a mix of customer types, a significant portion of its underlying businesses ultimately serve or directly impact individual customers, particularly through its HG Global segment, which focuses on home warranty and title insurance.

Therefore, focusing on the individual customers and ultimate beneficiaries of its services, the major categories of customers served by White Mountains Insurance are:

1. Homeowners: These individuals purchase home warranty policies, primarily through White Mountains' HG Global subsidiary, to protect their home's major systems and appliances from unexpected repair or replacement costs.

2. Homebuyers and Sellers: Individuals involved in residential real estate transactions who require title insurance, also through HG Global, to ensure clear property ownership and protect against potential defects or challenges to the property's title. This insurance is often a critical component of real estate closings.

3. Retail Investors in Municipal Bonds: While a substantial portion of the municipal bond market is institutional, individual investors who hold municipal bonds can be indirect beneficiaries of the financial guarantee insurance provided by Build America Mutual (BAM), another White Mountains subsidiary. This insurance enhances the credit quality and security of the bonds, providing an added layer of protection to investors against payment defaults by municipal issuers.

G. Manning Rountree, Chief Executive Officer

Manning Rountree joined White Mountains in 2004 and became CEO in March 2017. Prior to his appointment as CEO, he served as President of White Mountains Capital and President of WM Advisors from 2009 to 2014. Before joining White Mountains, Mr. Rountree worked with Putnam Investments as a Senior Vice President for two years and spent three years with McKinsey & Company. He has also served as Chairman of the Board at Build America Mutual Assurance Company since 2020 and as an Independent Non-Executive Director at Admiral Group Plc from 2015 to 2021.

Liam P. Caffrey, President and Chief Financial Officer

Liam Caffrey was appointed Chief Financial Officer of White Mountains on March 1, 2022, and also serves as President since June 2024. He is slated to become the Chief Executive Officer of White Mountains effective January 1, 2026. Before his tenure at White Mountains, Mr. Caffrey spent nine years at Aon plc, where his roles included CEO of Aon Affinity and global CFO of Aon Risk Solutions. Earlier in his career, he was a partner with McKinsey & Company and an Engineer at General Motors.

Giles E. Harrison, Executive Vice President and Chief Strategy Officer

Giles E. Harrison serves as Executive Vice President and Chief Strategy Officer for White Mountains. He is expected to become the President of White Mountains on January 1, 2026.

Robert L. Seelig, Executive Vice President and General Counsel

Robert L. Seelig holds the positions of Executive Vice President and General Counsel, and is also involved with Investor Relations for White Mountains.

Michaela J. Hildreth, Chief Accounting Officer and Managing Director

Michaela J. Hildreth has been the Chief Accounting Officer and Managing Director of White Mountains since May 2021. She previously served as Managing Director and General Auditor of WM Capital and held various accounting and auditing positions within White Mountains after joining the company in 2003. Prior to White Mountains, Ms. Hildreth worked at PricewaterhouseCoopers for approximately 13 years.

Key Risks to White Mountains Insurance (WTM)

1. Investment and Market Volatility: White Mountains Insurance is exposed to significant risks from fluctuations in financial markets and interest rates. The company invests in interest-rate-sensitive securities, and its financial results can be materially impacted by realized and unrealized investment gains and losses. For example, the company reported a substantial loss in Q1 2020 driven by net realized and unrealized investment losses, and more recently, unrealized investment gains have influenced its results. The strategy of managing capital through investments and exits also exposes the company to market timing risks.
2. Catastrophic Events and Underwriting Risk: As an insurance and reinsurance company, White Mountains is inherently vulnerable to claims arising from catastrophic events, including hurricanes, windstorms, earthquakes, floods, wildfires, and other severe weather occurrences. These events can lead to significant losses, as demonstrated by the impact of the January 2025 California wildfires on the company's WM Outrigger Re segment, which experienced a significantly higher combined ratio due to related losses.
3. Competitive Industry and Regulatory Changes: The insurance industry is highly competitive, and White Mountains faces ongoing pressure from both established market participants and new entrants. This intense competition can impact the company's ability to maintain its market share and profitability. Additionally, the insurance sector is heavily regulated, meaning that changes in domestic or foreign laws, regulations, or their interpretation could materially affect White Mountains's operations, financial condition, and business strategy.

White Mountains Insurance Group (WTM) operates in several distinct markets. Here's an overview of the addressable market sizes for its main products and services:

Property and Casualty (P&C) Insurance and Reinsurance

• U.S. Property and Casualty Insurance Market: The U.S. property and casualty insurance market was valued at approximately $1.0 trillion in 2024 and $1.10 trillion in 2025. Some estimates place the market size at $890 billion in 2024, with projections to reach $2.02 trillion by 2034. Another source noted net premiums written in the U.S. totaled $932.5 billion in 2024 for the P/C sector. This market is projected to reach $1.33 trillion by 2030, growing at a 3.96% CAGR.
• Global Property and Casualty Insurance Market: The global property and casualty insurance market was valued at $3.97 trillion in 2024 and is projected to reach $8.81 trillion by 2034, with a compound annual growth rate (CAGR) of 8.30% from 2025 to 2034.
• Global Reinsurance Market: The global reinsurance market was valued at $498.7 billion in 2021, $581.3 billion in 2024, $469.70 billion in 2025, and $711.75 billion in 2024. It is projected to reach $1.34 trillion by 2031, growing at a CAGR of 10.8% from 2022 to 2031. Other forecasts estimate it to reach $1.16 trillion by 2033 (CAGR of 8.04% from 2025-2033), $629.70 billion by 2030 (CAGR of 6.04%), and $2.0 trillion by 2034 (CAGR of 10.88% from 2025-2034).
• U.S. Reinsurance Market: The U.S. reinsurance market size exceeded approximately $109 billion in 2022. The U.S. market was valued at $220.05 billion in 2024 and is expected to reach $630.10 billion by 2034, with a CAGR of 11.09% from 2025 to 2034.

Municipal Bond Insurance

Information on the specific addressable market size for municipal bond insurance was not readily available in the search results, making it difficult to provide a distinct market size for this product line. Therefore, the addressable market size for municipal bond insurance is null.

Capital Solutions for Asset and Wealth Management Firms (Kudu segment)

White Mountains, through its Kudu segment, provides capital solutions to boutique asset and wealth managers. The addressable market size for this specialized service is not quantifiable from the provided search results. Therefore, the addressable market size for capital solutions for asset and wealth management firms is null.

Insurance Solutions for the Travel Industry

White Mountains' "Other Operations" segment offers insurance solutions to the travel industry. Information on the specific addressable market size for insurance solutions for the travel industry was not readily available in the search results, making it difficult to provide a distinct market size for this product line. Therefore, the addressable market size for insurance solutions for the travel industry is null.

• Strategic Acquisitions and Capital Deployment: White Mountains has demonstrated a clear strategy of acquiring and integrating businesses to expand its portfolio. Recent examples include the acquisition of Enterprise Solutions and the agreement to acquire a majority interest in Distinguished Programs. The company also closed its transaction with BroadStreet Partners. Furthermore, the sale of approximately 77% of its equity interest in Bamboo is expected to significantly increase undeployed capital to $1.1 billion, which White Mountains is poised to use for further strategic investments in the near future. This ongoing capital deployment into new businesses is a key driver for future revenue expansion.
• Growth in Existing Operating Businesses: Core segments like Ark, HG Global, and Kudu are consistently contributing to revenue growth. Ark has shown strong performance with growth in gross written premiums and favorable combined ratios. HG Global has also reported growth in gross written premiums and book value. Kudu continues to generate a notable return on equity and grow the fair value of its portfolio of participation contracts, indicating steady revenue contributions from its asset management activities.
• Expansion within Specialty Insurance Platforms: The acquisition of Distinguished Programs is specifically aimed at expanding White Mountains' specialty insurance platform. This move allows for further penetration and growth in niche insurance markets. Additionally, the Ark segment has been expanding its underwriting teams and adding new classes of business in property and specialty lines, contributing to organic growth in these profitable areas.
• Investment Returns from the Consolidated Portfolio: While subject to market conditions, investment income plays a role in White Mountains' overall revenue. The company actively manages its investment portfolio, which contributes to its total revenues. With an increased amount of undeployed capital following the Bamboo transaction, White Mountains has a greater capacity to make strategic investments that can generate further investment returns and, consequently, revenue growth.

Share Repurchases

• White Mountains completed a "modified Dutch auction" self-tender offer in September 2022, repurchasing 327,795 common shares for approximately $461 million.
• In the year ended December 31, 2022, White Mountains repurchased and retired 461,256 common shares for $616 million.
• As of December 31, 2024, the company was authorized to repurchase an additional 301,014 shares under board authorizations that do not have a stated expiration date.

Share Issuance

• Performance share payments for the 2021-2023 and 2020-2022 performance cycles were made in March 2024 and March 2023, respectively.
• During the three months ended March 31, 2024, White Mountains granted 10,405 performance shares for the 2023-2025 performance cycle.

Inbound Investments

• In 2022, White Mountains, along with Massachusetts Mutual Life Insurance Company and Kudu management, participated in Kudu's equity capital raise of $115 million, with Mass Mutual contributing $64 million.

Outbound Investments

• White Mountains launched White Mountains Partners (WTM Partners) in October 2023, with plans to deploy up to $500 million of equity capital over time into businesses in non-insurance sectors such as essential services, light industrial, and specialty consumer.
• In late 2023, White Mountains announced a planned $285 million investment to acquire approximately 70% ownership of Bamboo Ide8 Insurance Services, LLC, specializing in California homeowners' insurance, with the transaction expected to close in early 2024.
• In July 2025, White Mountains agreed to acquire a 51% controlling interest in specialty insurance program manager Distinguished Programs for approximately $230 million in cash, with closing anticipated in the third quarter of 2025.