This article explores a new model of Islamic boarding schools in the modern era. Various innovations appear to be made as an urgent change to Indonesia’s educational system. “Pesantren entrepreneur” is, among other, a new way (manhaj) of Indonesia’s contemporary education to reduce unemployment and overcome poverty. The concept is that students (santri) are not merely taught such religious lesson (tafaqquh fî al-dîn) but they also trained to be able to understand and possess ability within economics aspect (tafaqquh fî al-tijârah). It is assumed that the more pesantren entrepreneur are established the stronger the nation’s economy will be. It has been undeniable fact that Indonesia’s independent and its development have been strongly supported by Islamic educational system, namely Islamic boarding schools (pesantren) which widely spread across Nusantara. The implementation of pesantren entrepreneur has been initiated from a strong desire to develop pesantren through active, creative, productive and innovative actions which will subsequently provide pesantren chance to independently maintain its existence. The author argues that such an effort will be able to create better future for our next generation.