Objective: To investigate the association between attention-deficit/hyperactivity disorder (ADHD) symptoms and entrepreneurial profiles and the effects of entrepreneurial characteristics in individuals who screen positive for ADHD and self-identify as entrepreneurs. Methods: We sent 4,341 questionnaires by e-mail to applicants for a career development course for entrepreneurs. We used the propensity score covariate adjustment to balance differences between included and excluded individuals. ADHD symptoms were evaluated with the Adult ADHD Self-Report Scale. The Individual Entrepreneurial Orientation scale was used to assess the entrepreneurial profile of the participants. Impairment from ADHD symptoms was assessed with the Barkley Functional Impairment Scale. Results: Those who screened positive for ADHD had higher risk-taking scores (p-value = 0.016) and lower proactivity (p-value = 0.001) than those who screened negative. Higher inattention scores were related to lower proactivity (p-value < 0.001), while higher hyperactive symptom scores were related to a more generalized entrepreneurial profile (p-value = 0.033). Among ADHD-positive participants, entrepreneurial profile scores were not significantly associated with company profits or impairment. Conclusions: Inattention symptoms were related to less proactivity, whereas hyperactive symptoms were positively associated with a general entrepreneurial orientation. ADHD-positive individuals had a higher risk-taking profile, and these characteristics did not negatively impact their lives.