This article considers whether ex-incarceree/convict status favorably conditions the decision to be self-employed—a proxy for entrepreneurship. With data from the U.S. General Social Survey, we estimate the parameters of simple Probit and Bivariate Probit treatment specifications of individual self-employment outcomes as a function of ex-incarceree/convict status, and several measures of individual risk-taking propensities. Parameter estimates reveal that ex-incarceree/convict status has a positive and significant treatment effect on self-employment, particularly for Black Americans, after controlling for various measures of individual risk propensities. Our results suggest that the expansion of entrepreneurship training programs and the elimination of any barriers that restrict access to start-up capital for ex-incarcerees/convicts would reduce crime and recidivism, ameliorate mass incarceration, and complement pro-growth economic policies that induce more self-employment and entrepreneurship. JEL Classification: J01, J24, L26, Z13