Carollo was born in Caccamo Sicily and lived in Chicago before he moved to Florida. During his time in Chicago he was a reputed associate of the Chicago Outfit. He is the cousin of imprisoned Philadelphia crime family boss John Stanfa, and related to the New Jersey faction of the Sicilian Gambino Family. He allegedly became a soldier in the Tampa crime family in the 1980s, he was reportedly brought into the family by Vincent LoScalzo. His legitimate activities include that of a property developer in Pasco County, Florida and he once served as the manager for the Quail Hollow Country Club, which is now owned by one of his sons, Andre Carollo.