<p>From the innovation among pesantrens, students need not only Islamic religious learning but also entrepreneurial skills. This research explores the entrepreneurship learning model that had been developed by Pondok Pesantren Riyadlul Jannah Pacet and Pondok Pesantren Sidogiri Pasuruan and examines the effectiveness of pesantren entrepreneurs. This study used a descriptive qualitative method. In order to obtain the data validity, the data triangulation method supported by documentation and observation was employed by conducting interviews with kyai, asatidz, santri, and graduate users. The research objects were Pondok Pesantren Riyadlul Jannah and Pondok Pesantren Sidogiri Pasuruan; both are pioneers in developing pesantren entrepreneurs in Indonesia. This study showed that pesantren entrepreneurs are able to equip and encourage students to get careers towards prosperity. By harmonizing the theories of Kasb Asy’ariyah and Locus of Control, the focus of this study was on students who were not only capable as mubaligh, but also as entrepreneurs, particularly if they continued their studies at pesantren.</p>