Effective political leadership demands some ability to get along with others and to conform to rules set by legislation that came before you. The provinces don’t take orders from you and people like O’Leary don’t get to dictate terms. 
If he keeps sending the message that he really couldn’t care about how governance works he won't be the last man standing. When you own your own business, you can do solos, but rogue politicians usually get pushed aside . Trump is learning that governing is not the same as sitting in Trump Tower and giving orders to corporate employees. O'Leary will find out too.