Soft, challenging, and entrepreneurial skills are competencies that cannot be separated from each other in a person's ability to succeed in entrepreneurship. Pesantren Entrepreneur al-Mawaddah is the only boarding school in Kapubaten Kudus that makes the philosophy of gushing the foundation of his education. This research aims to discover pesantren's strategy in cultivating the entrepreneurial spirit of Santri, the wantrepreneur's interpersonal skills, and the application of the gushing philosophy. This research is qualitative research using a case study approach. The data analysis techniques used in this study are documentation, interviews, and observations. The study is based on the CMM (Coordinate Management of Meaning) theory by W. Barnett Pearce and Vernon Cronen. The results of the study showed that: (1) motivation and entrepreneurship training as a way to foster interest and entrepreneurial spirit santri, (2) interpersonal skills possessed by an entrepreneur that is a noble practice, good communication skills, ability to negotiate, able to divide time and solve a business, (3) The application of the philosophical value of gushing is to educate students who are noble practice, good at recite Quran and doing business.
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