gistfile1.txt

$ruby -v
ruby 2.4.1p111 (2017-03-22 revision 58053) [x86_64-darwin14]

$rvm osx-ssl-certs status all
Selected SSL certs for: ruby-1.9.2-p290
cURL certificate bundle /usr/share/curl/curl-ca-bundle.crt not found
Certificates bundle /usr/local/etc/openssl/cert.pem is up to date.
Certificates bundle /etc/openssl/cert.pem is up to date.
Certificates bundle  is old.

$gem install bundler
ERROR:  While executing gem ... (Gem::Exception)
    Unable to require openssl, install OpenSSL and rebuild ruby (preferred) or use non-HTTPS sources

$rvm osx-ssl-certs update all
Selected SSL certs for: ruby-1.9.2-p290
cURL certificate bundle /usr/share/curl/curl-ca-bundle.crt not found
Updating certificates bundle /usr/local/etc/openssl/cert.pem: Already up to date.
Updating certificates bundle /etc/openssl/cert.pem: Already up to date.
Updating certificates bundle : Empty path passed to certificates update, functions stack: requirements_osx_update_openssl_cert_run __rvm_osx_ssl_certs_update_for_path __rvm_osx_ssl_certs_run_filter_and_run __rvm_osx_ssl_certs_run __rvm_osx_ssl_certs_update __rvm_osx_ssl_certs source __rvm_run_wrapper rvm
Failed.