Michael is speaking from a broad base of experience, one that is not just a hero's epic of one success after another with a token failure before the ultimate victory. From the heroic perspective (PG, Zuck, Gates, etc.), every setback is but a small dip before eventual triumph. These people sincerely believe that anyone can do what they have, and as a result their worldviews are extremely limited and naive. In a way, they cannot know the other side of the story, because they have never experienced any other outcome.
The cold truth is that the situation Michael describes is reality for the vast majority of the working world. The darling VC-fund kids are a tiny minority, selling hopes and dreams to the masses in exchange for their servitude as employees who will never join their ranks.
It is very hard to see the system as a whole when one is so deeply immersed in one side of it. VC startups will not save the common man. If anything, they will put him out of work and ask him to "retrain", putting him in massive debt for an entry level position making far less than his previous job.
All this being said, I am extremely optimistic for the future, but I understand that the US requires significant structural reform if everyone is to benefit from technology. Not everyone can be a successful startup founder or programmer, and as soon as we accept that, we can move onto an earnest conversation about what needs to be done to make a better future for all, elite and commoner alike.