These are my thoughts after the first 20 minutes. Even though he seems to be much more calm than he used to be, he still is more garrulous than a preacher with Alzheimer's and 20 minutes was all I could really take.. When someone can't keep his answers concise and repeats himself, I get bored.
I'll start off with what I liked. I think he said, to paraphrase Chomsky, a lot of "nice words." That is, things that sounded good, but when you look closer into it, they don't really mean anything in his capitalistic world.
The first thing was that if you get stolen from, it's okay to steal it back. This is a classic Anarchist theory and it's usually expounded when workers take back factories or redistribute land. Since he's obviously hostile to unions and is an avid capitalist who is convinced he is right, I doubt he wants to test Syndicalist values or at the very least Geolibertarian ones against any of his own.
The second was that you should live your values. These, again, are nice words. I totally agree with them. But it's not like he's all that great at applying them. When I posted my email exchanges with him, he asked me to take them down and what I inferred was that he was threatening legal action. Doesn't sound too Anarchistic or Non-Aggressive to me, but oh well. Also, the line about "taking a bullet so you can look in the mirror" didn't really make a lot of sense. How can you look in the mirror if you're dead?
Finally, something I also agreed with: that in a strictly capitalistic society, only rich people could afford to get history degrees. He doesn't seem to have a problem with this, even though for one it is highly inefficient (some great would-be-historians might not realize their potential) and also would warp the historic record towards the rich and powerful's point of view.
On to my criticisms.
First, the kid has obviously been a victim of wage slavery: he can learn, but only if he works for two years to pay off his "debt." Now obviously teachers should be paid but its not like that's where all or even most of the money goes. Years of labor is a heavy price for a little bit of school. I would think he would be all over this, as it would fit into his allegation of institutional academia being a "controlling environment." But of course, this is just sour grapes from his experiences, and not based on any sort of objective analysis.
Second, he compares the Department of Defense to the Mafia which is incredibly accurate to say the least, with one distinction: the Department of Defense has mechanisms (however weak) of popular control. Not only are documents eventually declassified, but it is accountable to other branches of government, and (weakly) to the people, unlike the Mafia. Nobody cares about a Mafia whistleblower!
Third, he compares the state to slavery. Now the state is a lot of things but is not by definition a slave master. Yes there are taxes, but that's not exactly like being forced to work under grueling conditions for no pay. In fact the state can regulate working conditions. (As a side note, did anybody know who he was talking about when he mentioned "free"-market Union members?) And it's not like if you abolish the state you end the "sucking on the teets of power." You just get different teets, namely, corporations- oh wait - same teets.