Maybe it's just a case of what he is doing is a dramatically more difficult and challenging than what the majority of us can remotely understand. And that would mean things don't go the way he planned a significant amount of the time (perfectly normal). And that includes the whole spectrum of business operations -> investors, funding/finance, marketing, technology, distribution, supply chains etc.
I know from the comfort of our desk chair (with no risk taken, no relevant experience, no nothing really) and with perfect 20/20 hindsight we can make these criticisms but really they dont mean much.