Jack is left liberatarian, Thiel is right liberatarian. I've studied Thiel quite a bit, haven't studied Jack as much. It's also possible that they are both left in pre-2015 era, but the left has moved further out today (likewise, the far right is unrecognizeable today). I consider them all intellectuals and interesting.
I'm not sure being left libertarian is compatible with being a CEO as left libertarianism calls for abolishing private ownership of the means of production... (maybe elected CEO of a coop might be compatible with those views? either way, nothing like what Twitter is doing)
