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From the facts that numerous regions with initially similar economic conditions end up with different levels of entrepreneurial agglomeration, this paper constructs a model assuming that the sequential entrants make their career choices based on existing entrepreneurial ratio and describing the dynamics of entrepreneurial agglomeration formation. After mathematical analysis and numerical simulation using NetLogo, it is found that under social selection, a nonlinear Polya process with self-reinforcing and path-dependency characters will emerge, and the repeated entrants’ career choices will lead to the agglomeration of entrepreneurship; the agent’s risk compensation value, the initial population of agents, the number of role models in the early stage and the initial entrepreneurial ratio are determinants to the formation of entrepreneurial agglomeration. The findings confirm that entrepreneurship has “memory” and the entrepreneurial history could have influence on the future. In order to forge the entrepreneurial agglomeration, our suggestions include exerting influence on the determinants from an early age, and improving the individual’s risk-taking abilities.