He is basically arguing that information cannot be free in the future because of the need for an information economy to replace the economy of goods and services that will soon be produced by AI/ML and automatons.

He argues that AI/ML create successful business (e.g. insurance providers which can use algorithms to ensure they only provide their service to those least likely to need it) that essentially radiate the risk out to society and, ultimately, society cannot absorb the risk.

I found this part about democracy and spying interesting:

    And so you can’t have democracy in a highly evolved 
    information society if information is free. You just   
    can’t. I mean, because you’ll be giving the government 
    an infinite spying license. And it might sound like an 
    odd idea, but I hope once you roll it over in your 
    brain, you’ll start to see that it’s just a very simple 
    and sensible idea.

While the ideas he presents are interesting, that may be all they are. It is difficult to imagine them being played out in real life.