At this point, Micheal Saylor can afford to say whatever he wants. We are not all on the same level financially, geographically, politically and socially.
It is possible to for him to say that he can I invested what I can not afford to loose but I know I can't do that. If I do so, I'll become homeless and a mockery to people. For me, it is still to invest what I know I can afford to lose together with DCA. We are not on the same level and I do not have rich friends to bail me out if I go broke.
Risk management on a retail level and on a bigger level is a different set of skills and ideas - truly.