 In January 2014, on "The Lang and O'Leary Exchange", O'Leary remarked, 

O'Leary later clarified these statements, saying, 

O'Leary has produced and hosted his own reality show, "Redemption Inc.", in which he tries to help ex-convicts start and develop their own businesses.Having also been a co-host of "SqueezePlay" on Bell Media's Business News Network (BNN), he returned to the Discovery Channel on 1 September 2014 to join as a contributor for its radio and television stations such as CTV.On 5 May 2015, O'Leary made an appearance on the game show "Celebrity Jeopardy" and received $10,000 for his charity despite finishing 3rd and in negative points after both Double Jeopardy and Final Jeopardy rounds.