Design thinking (DT) is expanding its horizons across a variety of different domains. One of the early and debated contributions regarding DT addressed its relationship with the entrepreneurial field. Today, there are numerous contributions that design thinking can offer in the creation of new ventures. However, there are few examples in the literature that discuss the concrete impacts and benefits of adopting DT in this field, demonstrating it through entrepreneurial projects. This paper aims to explore practitioners’ experiences with the application of theories from design thinking inside an entrepreneurial context. The impacts of the learning and the relative application of the main design thinking principles are evaluated via a sample of 50 participants in an international summer academy that offered education on DT concepts and practices. Through this research, a deep understanding of how design thinking can contribute to entrepreneurship is provided, highlighting which specific DT abilities enable the development of entrepreneurial activity.