I suspect Condé Nast's advertising operations didn't mesh well with Reddit's audience. Within Condé Nast, they were likely just an irritating drain on resource

I suspect Condé Nast's advertising operations didn't mesh well with Reddit's audience. Within Condé Nast, they were likely just an irritating drain on resources. If Reddit's going to monetize effectively (and that's a big 'if'), it needs to be operationally independent so it can get creative.