This essay examines the origins of a managerial class in American business by exploring the dynamic economic and cultural milieu in which merchants and clerks forged apprenticeship and employment relations in eighteenth- and nineteenthcentury northeastern cities. Apprenticeship unraveled as an institution in countinghouses and stores throughout this period, a casualty of the Revolutionary-era narrative touting economic opportunity and independence through the cultivation of character. Increased competition for clerkships in the early republic led to the establishment of waged relationships shorn of traditional obligations. Yet in an uncertain economic climate, apprenticeship endured in idealized form within an antebellum cultural debate about the meanings of success and the ways to achieve it. As clerks' work tasks, social status, and economic prospects changed, many attempted to hitch their hopes for advancement to the coattails of merchants with capital instead of starting their own businesses, decisions that foreshadowed the formation of corporate hierarchies in the late nineteenth century.