How to tell old-man Ruby to work with the new OpenSSL kids
tldr:
wget https://gist.githubusercontent.com/dbernheisel/82e9bf55d01fe167a815425f77a71cc4/raw/e0af0db1139448e6a32a80d8b94a750644c2d8af/old-jerk-ruby-ssl.patch -O ~/old-jerk-ruby-ssl.patch
RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl)" rbenv install --patch 1.8.7-p375 < ~/old-jerk-ruby-ssl.patchOlder Ruby versions (1.8.7 or older) were built with an old OpenSSL version in mind, so if we try to build old Ruby
