I think the most interesting part of this is that he starts the painting very differently than I (a non-artistic person) would. Instead of starting with an outline of the head and filling it in, he starts with the large patches of color, gradually adding more detail. Very cool.
Most of art school is unlearning the "natural" way one might draw and paint and relearning ways to look at things and build up paintings and drawings in a much more iterative and incremental manor.
What made people masters in the past was the triumph over fear. Much like typing on a computer when you think of the words that you are typing you type slower than if you just let your hands work the keyboard. The great artists of history overcame their fear and let their body and mind create. When you bypass the fear there is not the same struggle to master the medium. If there is no longer a barrier, you will get good media but everyone will be able to do it and it will no longer be great.