Can't remember exactly where it was I first saw/heard of Saylor but it was during a live interview, some time right after the MicroStrategy Bitcoin buy move. He seemed to me remarkably less evangelist than I'd taken him for, and to be fair, all the Jesus labeling on him has really not been of his own making. His buying now merely keeps him in line with the strategy he's set on for his company, though I don't follow him or anyone enough to know if he's helping it along.
I'm not criticizing Saylor here, but rather how a large part of this community has turned him into a celebrity. People shouldn't just blindly copy his strategy and buy Bitcoin whenever he tweets that he bought. This basically gives him power to influence the market in short term. We are not gaining anything from it, just creating a risk.