It's sometimes very good content, other times you can tell he's talking out of his ass and trying to be edgy. A good "expert" should be able to admit that they have blind spots, and refer you to better sources of info.
His physical security video after the CTO of square died was not great. It felt too soon to be using his death to spread a message, and it relies far too heavily on the hypothetical idea that a gun could have saved him from harm. I understand that yes, a gun may have been able to prevent the attack, but it felt sort of ridiculous to insinuate that a gun is necessary to avoid a situation like this.