Monastic Formation and Foundation
Both saints began their monastic life at the Konevets (Konev) monastery, living under the guidance of Saint Arsenius before beginning their own independent work.
Around 1395–1396, in the Pskov diocese at the River Omutch not far from Porkhov, they founded a wilderness monastery in honor of the Dormition of the Most Holy Theotokos. Sources place the hermitage in Demyansk county, approximately 65 versts from Porkhov, with the community formally established about 1412.
According to the tradition, Theophilus was the founder and was highly revered, while Elder Jacob is remembered as the one who set the monastery in order. The monastery took Theophilus's name in his honor.