Despite interest in the historically ambiguous position of small entrepreneurs in the occupational and class structure, there has been little investigation of the lives of small-scale self-employed workers during industrialization. Using data from the 1880 manuscript census, city directories, and R.G. Dun and Company credit reports for Detroit, Michigan, this study explores employment status ― self-employment versus wage employment ― as a basis of occupational stratification. Self-employed workers in industrial Detroit were more likely than wage earners to have possessed social and labor market advantages. While self-employed workers were diverse in the occupations they held, they were more homogeneous than wage earners in their social characteristics and economic circumstances. The majority of self-employed workers were middle-class. Small-scale entrepreneurs formed a lower middle-class stratum in spite of similarities between their occupational experiences and those of manual wage earners.