The problem of cultivating students’ innovative and entrepreneurial ability is a non-negligible problem in the new era. This paper establishes a big data analysis model using a decision tree algorithm, assesses the entrepreneurial ability of higher vocational graduates based on the model as well as analyzes the differences in the entrepreneurial ability of students of different genders, then explores the influencing factors of graduates’ entrepreneurial ability, and carries out a correlation test of the influencing factors at each level. Finally, the entrepreneurial situation of higher vocational graduates was simulated and optimized, and the dilemma and breakthrough method of graduates’ entrepreneurial ability cultivation were analyzed. The simulation and optimization of vocational graduate entrepreneurship scenarios were carried out to analyze the dilemma and breakthrough methods in the cultivation of graduate entrepreneurship ability. According to the results, there is a correlation coefficient of 0.675, 0.695, and 0.876 between entrepreneurial ability at the national, social, and individual levels. From 2015 to 2022, when the investment of entrepreneurial capital, entrepreneurial resources, and entrepreneurial practice education is improved by 5%, the number of successful entrepreneurs will increase by 2, 1, and 5, respectively. This study helps to further enrich the theoretical system of innovation and entrepreneurship education in higher vocational colleges, and has significant theoretical significance in exploring the way of cultivating graduates’ entrepreneurial ability talents.