Hiloudaki was born in Sitia on the Greek island of Crete and was named Yiannis Greek for "John" , in honor of her deceased father, who had drowned at sea when attempting to rescue a woman. At an early age, Yiannis identified the need to pursue a gender transition and was able to obtain female hormones at the age of thirteen.
Hiloudaki went on to complete sex reassignment surgery at Charing Cross Hospital , in the United Kingdom, when she was twenty years old. Hiloudaki's affair with District Attorney Giorgos Sakellaropoulos, who met her while inspecting brothels in Rhodes , resulted in a national scandal.
After sex reassignment surgery , Hiloudaki became a top model in Greece, working with many Greek models and doing photoshoots for multiple Greek magazines. Hiloudaki was voted "Greek Woman of the Year" in Hiloudaki has appeared on several Greek television shows. Perhaps one of her most memorable TV appearances is the one on Tatiana Stefanidou's TV show Yalinos Tihos , in , on which she had been invited to talk about her then-newly released book.
During the conversation with Stefanidou, Greek singer Julia Barka , who was also a guest at the show and intended to release her own book after some months, interrupted the conversation when Hiloudaki said that Barka had not even started writing her book. Right after, Barka started talking with Hiloudaki and the new conversation was intense, while profanities were used.
On the show, she complained that residents of Sitia were accusing her of working as a prostitute and organising sexual orgies. Hiloudaki also claimed that many rumours were started by a lesbian student who was attracted to her and who decided to exact her revenge upon discovering that the feeling was not mutual.
