As for today, only a minimum part of the ICT potential for supporting innovative pedagogical developments and acquisition of key competences has been implemented in the lifelong learning sector. The STARTUP project aims at developing and analysing an innovative pedagogy and assessment approach, based on Open Educational Resources (OER), to support the diverse individual learning pathways and to better assess all types of learning outcomes and future learning needs related to entrepreneurship competences. The main project objective is the setting up of an innovative method for evaluating individual users learning needs to develop entrepreneurship, providing effective resources and setting up a peer review and sharing community to ensure the quality of the contents. Entrepreneurship is considered by the European Commission a very important key competence, especially in these times of economic downturns. From a practical point of view, it is a multilingual online environment where the individual learning needs of users meet selected and specifically contents, learning objects, collected from the available Open Education Resources repositories in a easy, effective and quickly way. The environment merges different existing technologies such as expert systems and open source software to set up a WEB community with the aim to provide the users with customized training path, based on their own learning style, specific needs, learning outcomes and the most effective digitised materials offered freely. The online peer to peer community is the place where all users could evaluate the Open Education Resources, share info and opinion about how to use, customize and finally re-use the contents. Our target is composed by educators, students and self-learners without any restriction in terms of sector, school, higher education and vocational education, in terms of user’s ages, young and adult people and role, learners/teachers/researchers.