How much does a CEO’s personality impact the performanceof their company? Management theory posits a great influence, but it is difficult to show empirically—there is a lack of publicly available self-reported personality data of top managers. Instead, we propose a text-based personality regressor based on crowd-sourced Myers–Briggs Type Indicator (MBTI) assessments. The ratings have a high internal and external validity and can be predicted with moderate to strong correlations for three out of four dimensions. Providing evidence for the upper echelons theory, we demonstrate that the predicted CEO personalities have explanatory power of financial risk.