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Old George's early milling operations laid the groundwork for the Douglas family's fortunes. Young George watched his father transform Iowa’s grain into prosperity, and after his father's death in 1884, he continued managing the family oatmeal business. In 1891, the family’s share of the Quaker Oats Company was acquired, providing Douglas with substantial wealth and fueling his entrepreneurial ambitions.
Inspired by technological advancements such as railroad expansion and mechanization, George sought to diversify. In 1894, he and his brother Walter founded the Douglas Company, initially producing linseed oil for paints and industrial purposes. Demonstrating a keen business acumen, they sold this venture profitably by 1899 and turned their sights toward corn—a mainstay in Iowa.