actually I'd argue he understands the problem pretty well. He talks about needing to offer something SO compelling they cannot help but interface with it, in spite of their desire for things that do not push them.
Has the number of people who want to learn decreased? If so, was it because of iPhones/iPads?
After learning one thing related to the topic I want to learn I still have 99 to learn but I don't even know what those 99 things are. So basically I'm learning through dumb luck. Yes the reason is that I haven't reached the magical "bootstrap knowledge" where you have enough information in your head to just look up the things I don't know.
Those youtube videos are nice and all but they will barely teach you anything, they are easy to consume low quality crap for lazy people. I know that because I'm one of them.
The fundamental problem is still the same. Discoverability sucks. I still have to ask someone who is more knowledgeable than me. So why not let the AI do that task?
My point is that the discoverability today is much better than it was, say, 30 years ago. Back then your options were: go to a library, find and read good books, or find someone knowledgeable, and go talk to him in person, or write him a paper letter with your questions, and hope he responds.
For example, I remember how I was given my first access to a computer, with a command prompt blinking on a black screen, and I had not a slightest idea about what to do with it. Oh, and people nearby were not particularly keen on stopping what they were doing and explaining things to me. I was given a poorly translated DOS manual and a few simple BASIC programs to study. My computer access was limited to one hour, twice a week, and I remember how I thought this was so cool, and that I want to learn.
On the other hand, things can (and probably will) get better organically. The iPad/iPhone is only 10 years old. In that time it has improved both in terms of hardware (e.g. stylus for iPad, 3d touch, extra sensors, slo-mo video recording), and software (voice recognition, Siri, AppStore, multi-tasking, StreetView, even something as simple as cut and paste - none of that was available in iOS 1!). In a few years we will move to smart glasses and virtual/augmented reality. My guess is it will make learning experience better for everyone.