Karaiskakis was born in the 1880s in Bogdanci, then Ottoman Empire (now North Macedonia). In 1904 he was ranked in "Macedonian Defense" and took action with his body in the areas of Gevgelija, Bogdanci, Strumica and Polykastro against Bulgarian komitadjis. Particularly in the area of Polykastro he became the fear of the komitadjis, who used that area as their hideout. He collaborated with various Greek armed forces as the chieftain of his own team and after he had exterminated the komitadjis in the lakes of Artzanis - Amatotovos (now dried), he acted in the region of Strumica, where he fought against the Bulgarian komitadjis until the revolution of the Young Turks in 1908. After 1908, new Bulgarian armed groups acted in Strumica who came from Bulgaria, so Karaiskakis rejoined the armed actions.