I generally agree with you about trying to redesign the interface. However, if you exercise some discipline, it can be a worthwhile way to sequence a gradual adoption of Emacs.
This is especially true for users of other programming-style text editors, such as Vi(m). Using Viper or similar can be a good way to ease into Emacs. It's even structured that way -- you can progress through the levels to gradually transition from Vim's way of doing things to the Emacs way. I did this myself.
As I said, it does require the discipline to periodically learn more and more features to progress. Aquamacs offers a similar transition for Mac OS X users.
"As you work your way forward in the venture funding process, the ratio of help to money increases, because earlier stage companies have different needs."
Isn't one of the points of the essay the fact that, as a company progresses, the amount of help from a VC decreases relative to the amount of money received?