Oh come on, the dude has autism. You can't expect to use an autistic person as an example of what normal skill acquisition is like. No, I don't expect the handicapped to be capable of the same things as fit. I don't expect a paraplegic to ever run in the Olympics, no matter how hard they try. On the other hand, I don't expect a blind man to become a painter, but it does happen.
I know someone who is clinically diagnosed with asperger's syndrome and I'm going to tell you now he was completely unable to detect when I was becoming annoyed with him. I eventually locked him in the other room and ignored him for 2 hours until his dad came to pick him up. Yet even after that he never picked up on my irritation towards him and suggested that we hang out more often. He actually is very smart as well but he is completely unable to pick up on what others are thinking. If you are suggesting that he could become normal or above normal through training I'm seriously doubtful...
So what are you saying? Henry in your original scenario has a mental deficiency of some kind, rather than a skill deficiency? If that is the case, how does that at all prove that persuasive skills are somehow more "powerful" than academic skills? And you still haven't addressed the fact that your own arbitrary scenario tries to make John out to be a dolt, and yet he still manages to get shit done and change the world.
"[John] reaches out to his talented friends and co-workers who admire him and he persuades a few of them to join his company." -- That's just good management! A successful company depends on more than just the efforts of one person. Get over this fantasy that you can live in your head and all by your lonesome become a millionaire.
"Over the next few years John is able to make a profit..." -- yeah, because he's a good manager.
"...despite making many blunders..." -- that happens to everyone, nobody knows exactly what to do all the time. Henry blundered on how to get funding and how to manage people. A much bigger blunder than "didn't make the thing right the first time".
"...he was always able to find the necessary funding to cover them." -- now you're contradicting your own scenario. If the funding is covering up the losses, then he never made a profit. So which way do you want your contrived scenario to go?