A common aim across many disciplines is to understand why it is that certain individuals attain unusually high levels of performance in their respective fields. The study of expertise in the field of entrepreneurship, however, is still in its infancy, as scholars strive to identify those personal, behavioral, and environmental characteristics that influence skill development. Prior expertise research indicates that the development of expertise is primarily driven by participation in intense, prolonged, and highly focused efforts of deliberate practice. The literature on deliberate practice suggests that individual self-regulatory characteristics are important components of long-term skill development. Consequently, this study seeks to explore the relationship between salient self- regulatory characteristics and the development of overall entrepreneurial skills. We hypothesize that there is a direct positive relationship between three different factors: (1) perseverance, (2) learning goal orientation, and (3) metacognition and entrepreneurial expertise. Additionally, we propose that the relationship between learning goal orientation and expertise is positively moderated by metacognition such that the relationship is more positive when entrepreneurs’ metacognition is high than when it is low.