Abstract: This study aims to analyze characterpreneurship leadership in strengthening pesantren-based entrepreneurship at Pesantren Al Haramain and Pesantren Darul Hikmah, West Lombok. Characterpreneurship is understood as a leadership practice that integrates character values, Islamic spirituality, and concrete entrepreneurial action through leader exemplarity. This study employed a qualitative approach using a collective case study design with an ethnographic orientation. Data were collected through semi-structured interviews, limited participatory observation, and document analysis related to pesantren business units. Data analysis involved data reduction, thematic coding, data display, cross-case synthesis, and conclusion drawing. The findings reveal four main themes: perseverance, humility, responsibility, and fighting spirit form the foundation of leadership; value internalization occurs through leader exemplarity in productive activities; business units such as agribusiness, Mini Bank, Haramain Bakery, NH-Mart, handicrafts, and herbal production function as experiential entrepreneurship learning spaces; and these practices contribute to students’ independence, work discipline, and responsibility. The study confirms that pesantren entrepreneurship should not be understood merely as an economic activity but also as an experiential character education process. The findings imply the need to strengthen pesantren entrepreneurship curricula by integrating leader exemplarity, business practice, and Islamic value reflection. Abstrak: Penelitian ini bertujuan menganalisis kepemimpinan characterpreneurship dalam penguatan kewirausahaan pesantren di Pesantren Al Haramain dan Pesantren Darul Hikmah, Lombok Barat. Characterpreneurship dipahami sebagai praktik kepemimpinan yang mengintegrasikan nilai karakter, spiritualitas Islam, dan tindakan kewirausahaan konkret melalui keteladanan pimpinan. Penelitian menggunakan pendekatan kualitatif dengan desain studi kasus kolektif dan orientasi etnografi. Data dikumpulkan melalui wawancara semiterstruktur, observasi partisipatif terbatas, dan analisis dokumen terkait unit usaha pesantren. Analisis data dilakukan melalui reduksi data, pengodean tematik, penyajian data, sintesis lintas kasus, dan penarikan kesimpulan. Hasil penelitian menunjukkan empat temuan utama: nilai ketekunan, kerendahan hati, tanggung jawab, dan semangat juang menjadi fondasi kepemimpinan; internalisasi nilai berlangsung melalui keteladanan pimpinan dalam aktivitas produktif; unit usaha seperti agrobisnis, Mini Bank, Haramain Bakery, NH-Mart, kerajinan, dan produksi herbal menjadi ruang belajar kewirausahaan; serta praktik tersebut berkontribusi pada pembentukan kemandirian, disiplin kerja, dan tanggung jawab santri. Penelitian ini menegaskan bahwa kewirausahaan pesantren tidak hanya dapat dipahami sebagai kegiatan ekonomi, tetapi juga sebagai proses pendidikan karakter berbasis pengalaman. Temuan ini berimplikasi pada perlunya penguatan kurikulum kewirausahaan pesantren yang menggabungkan keteladanan, praktik usaha, dan refleksi nilai Islam.
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