Gregory is reported to have been a student of the Aromanian philosopher Ioannis Chalkeus, a significant figure in the Greek Enlightenment.

[5] As a budding scholar, Gregory first arrived in Moscopole some time before 1730, according to historical author Robert Elsie.

It is not proven where he did his training for printing, though the Venetian printmaker Nikolaos Glykys in Venice is sometimes mentioned in this regard.

In the printing establishment of Voskopoja are known at least 14 acolytes published, mostly portraying local saints, used for liturgical purposes.

An edition from 1769, though considered by most scholars to be from Moscopole, it lack the name of the city, thus can not be attributed with certainty.

[11] Later in life, Gregory donated books to the local library, which was most probably destroyed in 1769 when Voskopoja was sacked.

[13] In 1932 the Bulgarian historian Ivan Snegarov was one of the first to propose the idea of two different Gregories living and working in Moscopole at the same time from 1731 to 1744.

[18] Furthermore, an engraving of his portrait from 1742 (see above) has his name written as "the Ieromonach Gregory of Moscopole and Printer",[19] revealing all of his occupancies, and proving this identity.

Gregory published his first work, Life of Saint Nikodemos in 1741, just a few years before he was given a new position at the New Academy in Moscopole.