This study examines the problems of entrepreneurship education at Vocational High School based on the perspective of teachers and school management characteristics related to the implementation of the curriculum in 2013 and trials of character-based education model. The research and development survey was conducted on a Vocational High Schools in East Java. Analysis description, experimental and entrepreneurial attitude tests were used to assess the findings of the field. The study was conducted for 2 (two) years. The results showed that more entrepreneurial teachers teach "the theory of entrepreneurship" than forming values and skills, related curriculum in 2013 (K-13). The teachers have difficulty in implementation, the experience of teachers to business practices and network with minimal business world. K-13 tends to lower and decrease the entrepreneurial spirit of students because of the lack of material changes in attitude, the school management does not undertake any major policy changes related to the implementation of this new curriculum. Model of learning by giving the module containing the business motivations of character-based and case studies are structured through the guidance of teachers can improve attitudes related aspects of confidence and motivation for entrepreneurship. Aspects of creativity, attitudes towards risk, initiative, responsibility and leadership is still low.