Ivan Lypa was born in Kerch, Taurida Governorate in a family of retired Imperial Russian army soldier, while his maternal line traces to Poltava region Cossacks who supported Ivan Mazepa.

Ivan Lypa in a church-parochial school at the Greek John the Forerunner Church in Kerch.

[1] Originally being offered to enroll in University of Dorpat Lypa declined[1] and in 1888 enrolled into medical faculty of the Kharkiv University where he became acquainted with number of notable Kharkiv students like Borys Hrinchenko and Mykola Mikhnovskyi.

Under influence from members of local Kharkiv hromada such as Dmytro Bahaliy, Oleksandr Katrenko, families of Rusov and Alchevsky, Lypa changed to purely Ukrainian national positions.

[1] In the summer of 1891 invited by the Russian statistician Aleksandr Rusov to help with a real estate census of the Poltava Governorate, Lypa along with other Kharkiv University students Mykola Baizdrenko and Mykhailo Bazkevych as well as Kyiv student Vitaliy Borovyk visited the Taras Shevchenko Grave (Taras Hill) near Kaniv and created Ukrainian national underground political organization, the Taras Student Fraternity (Brotherhood of Taras).