Skaat has been singing and performing in public since he was a child. At the age of six, he won a children's song festival competition. While still in elementary school he appeared on national television and as a teenager, he was the lead singer for both his city's and high school's bands. During his mandatory duty with the Israeli Defense Forces, he sang in the Communication Corps Band. Skaat's professional breakthrough came when he was a contestant on the second season of "Kochav Nolad" ("כוכב נולד", "A Star is Born"), a reality competition television show similar in format to "American Idol", and finished in second place. After the show ended, he signed a recording contract with Hed Arzi, one of the largest music companies in Israel.