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Wintrust Financial Corp is a financial holding company that provides community-oriented, personal, and commercial banking services to customers generally located in the Chicago metropolitan area, southern Wisconsin, northwest Indiana, and western Michigan. The company provides specialty finance services, including financing for the payment of property and casualty insurance premiums and life insurance premiums, and wealth management services to customers in its market area. Its operations consist of three primary segments: community banking, specialty finance, and wealth management. The company generates the majority of its revenue from the community banking segment.

Berkshire Hathaway is a holding company with a wide array of subsidiaries engaged in diverse activities. The firm's core business segment is insurance, run primarily through Geico, Berkshire Hathaway Reinsurance Group, and Berkshire Hathaway Primary Group. Berkshire has used the excess cash thrown off from its operations to acquire Burlington Northern Santa Fe (railroad), Berkshire Hathaway Energy (utilities and energy distributors), and the companies that make up its manufacturing, service, and retailing operations (which include Precision Castparts, Lubrizol, Clayton Homes, Marmon, and IMC/ISCAR). The conglomerate is unique in that it is run on a completely decentralized basis.