He later attended live events at the Nassau Coliseum and Madison Square Garden as well as a rare American Wrestling Association card at Ward Melville High School, where wrestler Mick Foley graduated from.
Sullivan eventually made his debut with his brother as the Freedom Ryders facing his future tag team partner Emory Hale and another wrestler in Bradenton, Florida.
He continued using the Freedom Ryder gimmick during his early career and eventually made his debut in IPW Hardcore for promoter Ron Niemi.
Returning to the independent circuit the following year, he participated in the 2001 ECWA Super 8 Tournament losing to Reckless Youth in the opening rounds.
Three months later, he and Buck Quartermain lost their titles to Scoot Andrews who became a triple crown winner with the IPW, FOW and NWA Florida Heavyweight Championships.
[3][4] Forming Naturally Marvelous, they joined Buck Quartermain and Pepi Prado in the Tampa Clique which would dominate the promotion during the next year.
Sullivan was unable to compete due to a family emergency, however, and he was replaced by referee turned wrestler Mikey Tenderfoot and lost the unified titles to the Shane Twins.
Defeated Rod Steel to become the number one contender for the NWA Southern Heavyweight Championship, he also won a five-way match between Sedrick Strong, David Babylon, Lex Lovett and Danny Doring on February 28, 2004.
Later that year, he defeated Lex Lovett, Buck Quartermain and Bruce Steel in a four-way match at an IPW Hardcore show on September 17.