$ bundle exec rails s
Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib (LoadError)

$ brew install https://raw.githubusercontent.com/Homebrew/homebrew-core/64555220bfbf4a25598523c2e4d3a232560eaad7/Formula/openssl.rb -f

The Ruby openssl extension was not compiled.

$ brew install rbenv/tap/[email protected]
Updating Homebrew...
==> Auto-updated Homebrew!
Updated 3 taps (homebrew/core, homebrew/cask and caskroom/cask).
==> Updated Formulae
Updated 13 formulae.
==> Updated Casks
inkscape                                                            inkscape

==> Tapping rbenv/tap
Cloning into '/usr/local/Homebrew/Library/Taps/rbenv/homebrew-tap'...
remote: Enumerating objects: 5, done.
remote: Counting objects: 100% (5/5), done.
remote: Compressing objects: 100% (4/4), done.
remote: Total 5 (delta 0), reused 5 (delta 0), pack-reused 0
Unpacking objects: 100% (5/5), done.
Tapped 1 formula (29 files, 28.6KB).
==> Installing [email protected] from rbenv/tap
==> Downloading https://www.openssl.org/source/openssl-1.0.2t.tar.gz
Warning: Your Xcode (11.0) is outdated.
Please update to Xcode 11.3.1 (or delete it).
Xcode can be updated from the App Store.

==> perl ./Configure --prefix=/usr/local/Cellar/[email protected]/1.0.2t --openssldir=/usr/local/etc/openssl no-ssl2 no-ssl3 no-zlib shared e
==> make depend
==> make
==> make test
==> make install MANDIR=/usr/local/Cellar/[email protected]/1.0.2t/share/man MANSUFFIX=ssl
==> Caveats
A CA file has been bootstrapped using certificates from the SystemRoots
keychain. To add additional certificates (e.g. the certificates added in
the System keychain), place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/[email protected]/bin/c_rehash

[email protected] is keg-only, which means it was not symlinked into /usr/local,
because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries.

If you need to have [email protected] first in your PATH run:
  echo 'export PATH="/usr/local/opt/[email protected]/bin:$PATH"' >> ~/.bash_profile

For compilers to find [email protected] you may need to set:
  export LDFLAGS="-L/usr/local/opt/[email protected]/lib"
  export CPPFLAGS="-I/usr/local/opt/[email protected]/include"

For pkg-config to find [email protected] you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/[email protected]/lib/pkgconfig"

==> Summary
🍺  /usr/local/Cellar/[email protected]/1.0.2t: 1,787 files, 12.0MB, built in 8 minutes 8 seconds

openssl -> ../Cellar/[email protected]/1.1.1g

$ RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/[email protected]" rbenv install 2.0.0-p648 
Downloading ruby-2.0.0-p648.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.0/ruby-2.0.0-p648.tar.bz2
Installing ruby-2.0.0-p648...

WARNING: ruby-2.0.0-p648 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: use readline from homebrew
Installed ruby-2.0.0-p648 to ~/.rbenv/versions/2.0.0-p648

rbenv: cannot rehash: ~/.rbenv/shims/.rbenv-shim exists

$ gem install bundler
Fetching: bundler-2.1.4.gem (100%)
ERROR:  Error installing bundler:
        bundler requires Ruby version >= 2.3.0.

$ gem install bundler -v "1.17.2"

$ bundle exec rails s
...
~/vendor/bundle/ruby/2.0.0/gems/activesupport-4.0.0/lib/active_support/dependencies.rb:228:in `require': dlopen(~/vendor/bundle/ruby/2.0.0/gems/mysql2-0.3.20/lib/mysql2/mysql2.bundle, 9): Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib (LoadError)
...

---
BUNDLE_PATH: "vendor/bundle"
BUNDLE_BUILD__LIBV8: "--with-system-v8"
BUNDLE_BUILD__THERUBYRACER: "--with-v8-dir=/usr/local/opt/[email protected]"
- BUNDLE_BUILD__MYSQL2: "--with-ldflags=-L/usr/local/opt/openssl/lib"
+ BUNDLE_BUILD__MYSQL2: "--with-ldflags=-L/usr/local/opt/[email protected]/lib"

However, your system version of v8 could not be located. 

Please make sure your system version of v8 that is compatible 
with 3.16.14.15 installed. You may need to use the 
--with-v8-dir option if it is installed in a non-standard location
        from ~/workspace/project/vendor/bundle/ruby/2.0.0/gems/libv8-3.16.14.15/lib/libv8.rb:7:in `configure_makefile'
        from extconf.rb:32:in `<main>'

$ bundle update libv8
...
Fetching libv8 3.16.14.19 (x86_64-darwin-18) (was 3.16.14.15)
Installing libv8 3.16.14.19 (x86_64-darwin-18) (was 3.16.14.15)
...
Fetching therubyracer 0.12.2
Installing therubyracer 0.12.2 with native extensions
...
Bundle updated!