The one thing, though, is O'Leary doesn't have anywhere the same level of charisma that Trump has. Trump has that whole "Cult of Personality" aspect in which people will support him at any turn (Rob Ford had this too). I don't really see that character trait in O'Leary.
That said, the one advantage O'Leary has is he doesn't carry the "-isms" baggage that Trump has. From what I've read and heard, he's been an equal opportunity employer and has never spoken out against any particular group (unlike Kellie Lietch). His only foible might be that he's stated that massive income inequality is a "wonderful thing," but that didn't really deter working class people from voting for Trump either.
The hilarious thing is - I honestly think if he ran provincially, either in Alberta or Ontario (where he's spoken out against the government before), he'd probably win. Nationally, though? Even with a LOT of Trudeau supporters starting to lash out against him for breaking campaign promises, I don't see him carrying an election - especially without Quebec.