This is a pretty amazing analysis.
I think a lot of really talented engineers in Silicon Valley fit into a kind of hybrid category I might call 'loser with sociopathic tendencies' (gotta love these terms--hey, I didn't invent them, I'm just following the article). Although they deliberately choose to remain at the 'loser' level in terms of the org chart, they have a
'sociopathic' level of awareness of how the business operates (maybe from being an early employee or founder of previous startups). They're never truly comfortable at the 'loser' level, but maybe not willing or capable of making a move to the 'sociopath' level, and consciously avoid the 'clueless' level (which I think they eventually enter anyway, even if they avoid becoming managers, by entering some kind of 'emeritus' engineering position).
The article suggests that Toby might be in this category, which I didn't think fit at first, but maybe it does--this type of person seemed to me to generally be laconic, cultivated a high degree of irony about the nature of the organization and their role within it, and usually carried an 'escape plan' as a prominent part of their mental outlook (based on either past actual or future fantasized stock option earnings) --all quite similar to the Toby character.
I also think there's a type of person who views anyone at the 'sociopath' level as being inherently morally corrupt, and therefore preemptively excludes him/herself from ever reaching that level, even if they'd otherwise be capable of it. I don't think this is a correct view; the 'sociopath' type may just be the type of person who is more willing to face the full reality of how the business is run and make tough decisions that involve firing and so on. For example, even in the show I don't think the David Wallace character is portrayed as being particularly corrupt. Ryan, on the other hand, is purely selfish and greedy for power--but this actually causes him to fail at the higher levels (which I think often happens in real life as well).
(By the way, in case it's not obvious, I'm trying to use these terms in the sense they're defined in the article--I don't mean them to be truly pejorative to anyone operating at any of these levels.)