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Heritage Insurance Holdings, Inc., through its subsidiaries, provides personal and commercial residential insurance products. The company offers personal residential insurance in Alabama, California, Connecticut, Delaware, Florida, Georgia, Hawaii, Maryland, Massachusetts, Mississippi, New Jersey, New York, North Carolina, Rhode Island, South Carolina, and Virginia; commercial residential insurance for properties in Florida, New Jersey, and New York; and licensed in the state of Pennsylvania, as well as personal residential and wind-only property insurance. It also provides restoration, emergency, and recovery services; property management, and reinsurance services; homeowners insurance products, including single-family, homeowners or duplex, and condominium owners; and dwelling fire insurance policies. In addition, the company provides personal line policies through a network of retail independent agents, wholesale agents, and a partnership with a direct agency, as well as distribute indirectly to retail locations through wholesale agency relationships. Further, it offers personal and commercial insurance policies through a network of independent agencies. The company was founded in 2012 and is headquartered in Tampa, Florida.

Kingsway Financial Services Inc., through its subsidiaries, engages in the extended warranty and business services in the United States. The company operates through two segments, Extended Warranty and Kingsway Search Xcelerator. The Extended Warranty segment markets, sells, and administers vehicle service agreements and related products for new and used automobiles, motorcycles, and ATVs. This segment also markets and distributes warranty products to manufacturers, distributors, and installers of heating, ventilation and air conditioning, standby generator, commercial LED lighting, and commercial refrigeration equipment; and provides equipment breakdown and maintenance support services to companies, as well as after-market vehicle protection services. The Kingsway Search Xcelerator offers outsourced finance and human resources consulting services, including operational accounting, such as bookkeeping, accounting, financial reporting, and analysis and strategic finance services; technical accounting comprising initial public offerings, Securities and Exchange Commission reporting, and international consolidation services; human resources, workforce management, and compliance support services; and advisory services. This segment also provides financial executive services for project and interim staffing engagements; search services for permanent placements; healthcare staffing services to acute healthcare facilities for short-term and day-to-day needs of hospitals; software products for the management needs of all types of shared-ownership properties; and fully managed outsourced cardiac telemetry services, as well as provides mobile monitors to the hospitals. The company offers its products and services through credit unions and dealers. Kingsway Financial Services Inc. was incorporated in 1989 and is headquartered in Chicago, Illinois.

Maiden Holdings, Ltd., through its subsidiaries, provides property and casualty insurance and reinsurance solutions to regional and specialty insurers in Europe, North America, and internationally. It operates in two segments, Diversified Reinsurance and AmTrust Reinsurance. The company writes treaties on a quota share basis and excess of loss basis. It also offers auto and credit life insurance products through its insurer partners to retail clients; and underwrites risks on a retroactive basis, which provides a range of legacy services to small insurance entities. Maiden Holdings, Ltd. was founded in 2007 and is headquartered in Pembroke, Bermuda.

Metromile, Inc. provides insurance policies for automobile owners in the United States. It operates through two segments, Insurance Services and Enterprise Business Solutions. The company offers pay-per-mile auto insurance policies. It also provides The Pulse, a device that plugs into the diagnostic port of its customer's car and transmits data, such as miles driven, driving habits, phone use, speeding, hard braking, accelerating, cornering, and location over wireless cellular networks. In addition, the company offers access to its technology under software as a service arrangement, as well as professional services to third-party customers. Metromile, Inc. was founded in 2011 and is headquartered in San Francisco, California.