I think the glaring omission in Gruber's article, though, is Apple's lost advantage in Steve Jobs. It could be argued in the 11 years Steve Jobs was away from Apple that Mac hardware and software more or less coasted in terms of innovation.
The simple unibody design splintered into a dozen different beige boxes stacked on top of each other shortly after Job's departure in 1985. Mac OS gained color, cooperative threading, and a few peripheral updates until Steve Jobs came back in 1996. I'm not saying it was worse. I'm just saying it was uninspired incremental refinement. The design language at Apple didn't change from the day he left in 1985 until he finally came back in 1996.
And almost immediately after Steve comes back we've got OS 8 with its first UI facelift in years. System 9 quickly led into OS X. On the hardware front we got the bondi blue iMac. Then the iPod. Then the desk lamp-esque iMac G4. Not to mention the short lived G4 cube. Apple was alive again.
Now that Steve's involvement has once again diminished, what will Apple look like over the next decade? Will iOS 9 look that much different from iOS 5? Will the MacBook Pro evolve beyond a giant sized MacBook Air? Will Apple successfully branch out beyond phones, tablets and computers?
Tim Cook will keep Apple in fine shape. Apple will at worst be like Dell in its heyday. Delivering products people want at prices nobody could compete against, disrupting the traditional manufacturing process. But will Apple continue to successfully innovate? Companies tend to change to reflect the current leadership. HP was once a company that Steve Wozniak wanted to work at forever. In less than a decade after the founders were gone the the HP Way was gone and the company was never the same.
EDIT: I want to add this is mostly a counterpoint to Gruber who is clearly trying to diminish Jobs and glorify Cook. His brief treatment of the subject is to say Jobs brings "beautiful, elegant, innovative, and fun" before seemingly dismissing Jobs as merely a designer whose designs are something that get copied by other firms anyway therefore implying he is not a real competitive advantage unlike the "can't-be-copied" Cook operational competitive advantage.