This study examines how race and generational status shape self‐employment propensities and industry‐sector prestige among the self‐employed in the U.S. It draws on theories of assimilation, racialization, and a combined framework, racialized incorporation, to guide the analysis and interpret the results. It uses data from the U.S. March Current Population Survey (2000–2010) offering the first nationally representative examination of second‐generation self‐employment in the U.S. This study investigates three questions. First, do the odds of being self‐employed decline in the second and third generations? Second, do generational patterns in self‐employment propensities vary by race? And finally, do race and generational status affect the odds of being self‐employed in low‐, medium‐, and high‐prestige industry sectors? Results offer some support for the assimilation perspective: Immigrants are generally more likely than third‐generation groups to be self‐employed with the exception of Asians, where second‐generation Asians have the greatest odds of being self‐employed. However, results also reveal that generational patterns in self‐employment propensities vary by race and industry‐sector prestige. Accordingly, first‐ and second‐generation Whites have the greatest odds of being self‐employed (across all levels of industry‐sector prestige), and third‐generation Whites are more likely than all generations of Blacks and Hispanics to be engaged in high‐prestige self‐employment. These findings suggest that immigrants, their offspring, and native‐born groups undergo a racialized incorporation in which self‐employment is organized along hierarchical and racial lines associated with uneven levels of prestige.