On a Mac the best way to upgrade ruby and install the latest version of libusb, as well as many other useful command line tools is with Mac Homebrew. In a terminal enter each of these lines:
ruby -e \"$(curl -fsSkL raw.github.com/mxcl/homebrew/go)\"
brew install libusb libusb-compat ruby
You\'ll need an administrator account to install homebrew initially. This will download and compile the needed programs. I recommend against using those odd installer applications as they inject the software deep in to the heart of OS X and can potentially cause instability, and usually do not offer any simple means of uninstallation. Homebrew keeps all it\'s stuff in it\'s own directory and just uses shell paths to have things look there first, leaving it very easy to uninstall stuff and leaving system software using the libraries which came with the operating system.