Research indicates that individuals’ digital footprints, for example in Twitter and Facebook, can reveal remarkably valid information about their personality characteristics. In this study, we use digital footprints to gain insights into the personality of superstar entrepreneurs and managers, a largely understudied population in entrepreneurship research. Specifically, we compare the personality characteristics of 106 of the most influential business leaders employing a computerized text analysis tool based on the individuals’ Twitter messages (Receptiviti). Our findings are surprising and indicate that superstar managers are more entrepreneurial in many personality characteristics than superstar entrepreneurs. However, we also found some indications that superstar entrepreneurs seem to show features of a classic “Schumpeterian” entrepreneurial personality with respect to being creative, independent rule-breakers.