In recent history, different design approaches have been entering fields like management and strategy to improve product development and service delivery. Specifically, entrepreneurship has adopted a user-centric mindset in methodologies like the business canvas model and the value proposition canvas which increases the awareness of the users’ needs when developing solutions. What happens when a service design approach is used to understand the entrepreneurs’ experience through the creation of their startups? Recent literature suggests that entrepreneurial activity and success is conditioned by their local entrepreneurship ecosystem. This study investigates the Entrepreneurship Ecosystem of Medellín, Colombia - an ecosystem in constant growth but that lacks qualitative analysis. The sample consists of 12 entrepreneurs in early-stage phase. The data was gathered with two design research methods: Cultural Probes and Semi-structured interviews. The analysis of the information collected facilitated the development of 4 insights about the entrepreneurs and an experience map to visualise and interpret their journey to create a startup. The results of this study reflected the implications of the ecosystem, the explanation of the users’ perceptions and awareness and propose a set of ideas to the local government to improve the experience of undertaking a startup in Medellín.