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Although it is well established in the academic literature that entrepreneurs share common traits, there has been limited research dedicated to evaluating psychographic profiles of the self-employed. Using the Nominal Group Technique, the authors gleaned insight from a panel of experts in an effort to segment the self-employed based on personality traits and the benefits they receive from an entrepreneurial career. The findings show that self-employed individuals can be classified into four distinct segments: Exemplars, Generals, Moms and Dads, and Altruists. Each group derives different benefits from self-employment. Understanding these benefits can greatly assist entrepreneurship educators and marketers of small business oriented products and services.