Born in Brooklyn, New York and raised in Cleveland, Ohio, Bobish was an all-state wrestler and played football at Maple Heights High School before competing at Cuyahoga Community College, where he was a NCJAA All-American.
"[5] Bobish became interested in mixed martial arts by suggestions of friends in the bar where he bounced, The Flats, in which Ultimate Fighting Championships events were commonly ordered.
The American would find another wrestler and UFC veteran in the second round, Dave Beneteau, but Bobish controlled the bout with a guillotine choke with several strikes, eventually getting the win by a cut.
[6] He then fought yet another wrestler and UFC veteran, fellow NCAA collegiate champion Kevin Randleman from Team Hammer House, for the final.
[5] After the defeat, he returned to United States and joined Severn's team full-time, training with him, Don Frye and shootfighting teacher Becky Levi.
[6] Bobish returned at Vale Tudo Fighting 6 tournament, knocking out Ucimar Hypolito in six seconds in order to meet regarded Carlson Gracie's trainee Carlos Barreto in the semifinals.
In any case, minutes later Bobish started to show fatigue, and when he dove again in Barreto's guard to continue his ground and pound assault, he fell to a triangle choke submission.
Bobish advanced round and met another Hammer House fighter, fellow former NCAA Division I champion Mark Kerr, who opened their match with effective leg kicks and a takedown scored.
The American scored an early takedown and mounted Vovchanchyn, initially looking for a neck crank and later seeking a keylock, while applying ground and pound during the process.
Bobish scored a takedown and forced Hunt to turtle up, landing hammerfists and knee strikes and at one point even attempting a crossface hold on the kickboxer.
Bobish made his professional wrestling debut in March 2003 for Japanese promotion Fighting World of Japan, where he teamed up with his MMA training partner Don Frye to unsuccessfully face Kensuke Sasaki and Hiroshi Hase in their first match.