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In Des Moines, Allen quickly proved his business acumen, establishing a general store and a steam-powered sawmill. His energy and sharp instincts enabled him to seize opportunities in the burgeoning city. By 1855, at merely 26 years old, he diversified into banking and real estate. Allen amassed vast landholdings—at one point spanning over 93 square miles across Iowa—and gained a reputation as a daring investor willing to buy, develop, and finance almost anything. His efforts helped transform Des Moines from a frontier outpost into a thriving city.