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pry and rspec are gems. You had at least 3 rubies (system, rbenv, rvm), and each ruby puts its gems in a different folder. Your rspec might be in a folder for rbenv's ruby. If you switched to rvm's ruby, then bundle exec rspec would fail because rvm's ruby can't find rbenv's gems.
I'm not on a Mac. /usr/bin/ruby might be your Mac's system ruby. If you see the system ruby, it might cause "sudo" problems. You might need to change your PATH to switch rubies; rbenv's README might help.
NOTE:
The number of mentions on this list indicates mentions on common posts plus user suggested alternatives.
Hence, a higher number means a more popular project.