The 'plunk' you are describing is his ability to just 'get it done' - a trait I think most tech founders greatly underestimate. It's an ability or mental strength that makes a person able to will the project over the goal-line. I'm amazed how hard it is to complete anything - whether it's a startup app I'm working on or a piece of music - finishing it 100% and getting it 'in the can' is no small feet. It's special gift, and one that I would highly recommend anyone searching for a founder look for in their partner(s).
I have to admit I like Jeff, from his articles and such he seems to have a pretty clear way of thinking through big tech issues, and while he may sometimes surprise me with a 'lack of knowledge', I just remind myself that we all have gaps in our knowledge and at the end of the day, he's done some incredible work, and this 'lack' hasn't hurt him much (maybe it caused him to take longer to get to where he is, but he still managed to get it done).
For all we know it's his lack of knowledge that gives him an edge - he runs into something he doesn't get or hasn't been exposed too and dives in, eats it up because he needs to really know it. Compare that to a guy that takes a class on some esoteric aspect of coding, when he/she doesn't have any need to apply it, when they just care about getting a good grade - which person really has learned the material? Does the person that already learned it but didn't need it at the time have a really big advantage? They might work through the problem faster, so maybe that's the advantage - you save some time.
But I like the root of your point - one doesn't grow/learn without trying to hit their own limits and push past them. Good stuff man.
Theres one big difference between real life and (undergrad?) CS classes: the discovery phase. In most classes, the solution is laid out for you or implied in some way. Algorithms classes generally just consist of following a spec outlined by the book/teacher.
But when you run across a problem in real life it doesn't tell you to use a specific algorithm to solve it. Because of this, finding the solution usually requires a deeper level of knowledge.
When I graduated, that was the scariest part for me. Sure, I knew a bunch of algorithms, but I didn't have much practice in discovering when to use them and applying them to problems.
The funny thing is - esp. depending on how old you are - it is incredible how much easier it is to learn/find answers now. Pre-google it was tough - I frequented Barns & Nobles often to see what new books had arrived, or just to go find an answer in a book I knew they had.
But I digress... google/stackoverflow/etc have all made our lives so much easier.
The most important thing I learned in college was accepting/understanding criticism - not algebra or philosophy or how many moons orbit jupiter (all cool/good to know too btw).
Most other skills can be learned on your own. But think about how hard it is to learn to accept and understand criticism. If you receive it from your spouse, it usually causes a fight; or from a close friend or family member - ditto, also not good.
But being hammered in a peer-review style class where it would be somewhat absurd to think 'hey I'm right, my professor with 25+ years experience, not to mention the 15 other smart peers in my class, are all wrong'.
Of course there were always one or two people that really did think they were right and the professor/classmates were all wrong. They wonder why life is always so hard, and why the entire world is against them, never considering that it might be them having the problem, not the rest of us...
The other part of this though is that as a blog author, he has a desire and incentive to write about things that his readership might be interested in; so I have a feeling there is a certain amount of extra explaining, citations, and feigned not-understanding going on in his posts.
However, I would point out that formally trained people also have gaps. Just different ones that everyone is used to. The gaps of autodidatics stand out because they are unusual.
Autodidacts in general also have some strengths that are rare with formally trained people. (I don't have anything particular in mind. Just they spend their time with some different focusses and are bound to pick up some things that people who all follow the same curriculum didn't.)
So, yes autodidacts have some gaps, but this shouldn't be seen as a criticism.