By default, rubygems on mac installs executables in /usr/bin, rather than under gem dir in /Library/Ruby/Gems. However, these directories have different permissions:
~ $ ls -ld /usr/bin/ /Library/Ruby/Gems/
drwxrwxr-x 4 root admin 136 15 Nov 22:19 /Library/Ruby/Gems/
drwxr-xr-x 1085 root wheel 36890 11 Feb 22:57 /usr/bin/
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$ ruby -rubygems /Library/Ruby/Gems/1.8/gems/heroku-1.18.3/bin/heroku
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$ sudo gem uninstall heroku
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$ sudo gem update bundler
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$ bundle install
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