Maybe the world also needs people who are not so achievement-driven, who act as a kind of lubricant in the machine of society by making the environment around themselves lighter and more pleasant. And people who are that way should learn to value themselves and not feel guilty for not being as driven as some.
A world where everyone is a nose-to-the-grindstone overachiever seems like a pretty dreary one to live in.
And really is Viaweb that big of a deal? He got rich by selling .com in the .com bubble to another .com company. That wasn't so hard at the time. He wrote a good book on Lisp, and used his riches to invest and get richer. None of this seems particularly extraordinary. Does he somehow imagine Dropbox or Viaweb have transformed human experience? He writes a good essay, but he seems overly impressed by his own success.
A world where everyone is a nose-to-the-grindstone overachiever seems like a pretty dreary one to live in.