[11] Leftfield Pictures initially shot wedding videos while developing its entertainment content and clientele, and eventually sold its first series, The Principal’s Office, in 2008.
[13][11] Ultimately, Montgomery negotiated a deal with Gold & Silver Pawn Shop co-owner Rick Harrison, and pitched the show to the History Channel.
[17] In addition to Pawn Stars, other Leftfield Pictures series and Montgomery credits include Alone,[18] American Restoration and Counting Cars for History;[10] American Grit for Fox;[19] Bethenny & Fredrik for Bravo,[20] and National Geographic Channel’s specials Billy the Kid: The New Evidence (executive produced by Kevin Costner)[21] and Brain Surgery Live.
[10] Collectively, they produce series including FOX's The Four: Battle for Stardom[27] and Hell’s Kitchen; HGTV's Fixer Upper, Netflix's Queer Eye[28] and Girls Incarcerated,[29] A&E's Duck Dynasty and The First 48,[30] History's Pawn Stars, Alone and Forged in Fire.
[31] Bravo's The Real Housewives of New Jersey,[32][33] During Montgomery's tenure as CEO of ITV America, the company made production and talent deals with TV personalities and celebrities Michael Strahan,[34] WWE star John Cena,[35] Bethenny Frankel,[36] Good Morning America co-host Lara Spencer,[37] Grammy award-winner Timbaland and author/actress La La Anthony.
Montgomery was featured on the cover of The Hollywood Reporter on January 30, 2019, focusing on his new business, the Wheelhouse Group, and highlighting his contributions to reality TV.