I'm sure you've heard of the boring company which would revolutionize traffic except it did not and never will. He says "I have this idea make it work". This is the limit of his capability. In that way he's pretty similar to Elizabeth Holmes, except he isn't playing with the health of individuals for monetary gain.
I agree he is not just a 'luck' guy; he work(ed)(s) hard, is very persistent & pushes boundaries; he also knows how to manipulate the world successfully to pursue his goals, like Jobs & Gates & others before him. However, as far as we know, they weren't walking such a fine line close to fraud (although Gates was of course somewhat close to the illegal line with his anti-competitive actions in the EEE times).
Is this actually true? The only air-launched SpaceX project I could find was the cancelled Falcon 9 Air [1], which I don't think actually flew, and was years after the Falcon 1.
Was there some undocumented air-launched SpaceX project going on between 2002 and 2006?
The hyped private project I remember from around that time was SpaceShipOne[2], which won the "X Prize", but that was done by Scaled Composites, not SpaceX.
[1] https://en.wikipedia.org/wiki/SpaceX_launch_vehicles#Falcon_...
Musk is at worst comparable to people like Steve Jobs or Donald Trump: people with a near pathological need to prove that they deserve their wealth by taking stupid risks. Risks that sometimes pay off. For every Trump or Musk, there are probably ten rich sons who took stupid risks and failed so bad they didn't get to take such risks anymore.