Very good points. The author does try to disambiguate "loser" (though I don't think he does disambiguate "sociopath").

My problem with these terms is that they just can't be disassociated with their common meanings. This is a common rhetorical trick - an author defines the word one way, and sticks to that definition, but inevitably uses the impact of the more common word (while claiming that the earlier disambiguation clears him of the need to defend the more common usage).

In short, I think we need a different word than "loser" to describe the category of workers who 1) make a good salary 2) enjoy their work, and 3) yes, could make more money or get a better deal outside the organization.

I'm also unwilling to accept the use of "sociopath" to describe all start-up founders, no matter how airtight the author has been in locking down a definition that avoids all the negative connotations of the more general use of "sociopath."

I guess that I'm really just saying that some words just can't be disambiguated.

In this case, the ambiguity is in the interest of being humorous and interesting, which is why it doesn't bug me all that much (though in other contexts, it can be infuriating).