Ruby and “You must recompile Ruby with OpenSSL support or change the sources in your Gemfile”

This works for me:

rvm get stable

brew install libyaml

rvm pkg install openssl

rvm install ruby-2.0.0 --with-openssl-dir=$HOME/.rvm/usr

rvm use ruby-2.0.0

All credits go to https://coderwall.com/p/tptocq