Ruby has comparatively crappy documentation (still does, arguably worse now because the Pickaxe is no longer updated), and also had a very weak non-Rails English-language community, but comparison to Python (by rumor, it had a much stronger Japanese language community, but I can't attest to that.)

If you were doing something nontrivial where the interesting part weren't the kind of things Rails/ActiveSupport addressed, those factors alone (before even considering language/library features) made it a lot more of an uphill climb with Ruby.