While the study of personality differences is a traditional psychological approach in entrepreneurship research, economic research directs attention towards the entrepreneurial ecosystems in which entrepreneurial activity are embedded. We combine both approaches and quantify the interplay between the individual personality make-up of entrepreneurs and the local personality composition of ecosystems, with a special focus on person–city personality fit. Specifically, we analyse personality data from N = 26,405 Chinese residents across 42 major Chinese cities, including N = 1091 Chinese entrepreneurs. Multi-level polynomial regression and response surface plots revealed that: (a) individual-level conscientiousness had a positive effect and individual-level agreeableness and neuroticism had a negative effect on entrepreneurial success, (b) city-level conscientiousness had a positive, and city-level neuroticism had a negative effect on entrepreneurial success, and (c) additional person–city personality fit effects existed for agreeableness, conscientiousness and neuroticism. For example, entrepreneurs who are high in agreeableness and conduct their business in a city with a low agreeableness level show the lowest entrepreneurial success. In contrast, entrepreneurs who are low in agreeableness and conduct their business in a city with a high agreeableness level show relatively high entrepreneurial success. Implications for research and practice are discussed.