[1][2][3] Born around 1843 to the family of the small-time merchant and craftsman Gruyo Hlatev, Benkovski was a native of the bustling sub-Balkan town of Koprivshtitsa and had two sisters, Kuna and Vasilya.

[4] Due to his difficult childhood, Benkovski had to drop out of school after finishing third grade in order to be trained as a tailor by his mother and make a living.

For some ten years Benkovski lived in various cities of the old Ottoman empire, including Istanbul (Tsarigrad), İzmir (Smyrna) and Alexandria, engaging in various professions.

During his travels, Benkovski learned seven foreign languages to the level of basic competency: Arabic, Ottoman Turkish, Greek, Italian, Polish, Romanian and Persian.

His detachment was known as "The Flying Band" (Хвърковата чета, Hvarkovata cheta) because it toured the entire region tirelessly, mobilizing many insurgents and playing an important part in the fighting.

[7] In the wake of the uprising's suppression, Benkovski and the surviving members of the band (Stephen the Dalmatian, Zahari Stoyanov and Father Kiril) headed to the Teteven Balkan Mountains.