Issues installing OpenSSL with Ruby 2.2.6 on macOS Catalina

Question

Having an issue setup a rails app on my computer. Keep running into this issue with openssl and tried solving on my own but keep running into the same problem. Can anyone let me know what to do / if they have experienced anything similar?

OS: macOS Catalina v10.15.3

Ruby Version:

ruby-2.2.6

Gemfile:

source 'https://rubygems.org'

if RUBY_VERSION =~ /1.9/
  Encoding.default_external = Encoding::UTF_8
  Encoding.default_internal = Encoding::UTF_8
end

gem 'rails', '3.2.13'
gem 'rake', '10.4.2'
gem 'loggable'
gem 'json', '1.8.5'
gem 'gabba'
gem 'rvm-capistrano', require: false
gem 'rolify'
gem 'mysql2', '0.3.17'
gem 'test-unit', '~> 3.0'
gem 'therubyracer', '~> 0.12.1'
gem 'nokogiri', '1.5.9'
gem 'crack'
gem 'sanitize'
gem 'jquery-rails'
gem 'newrelic_rpm', '~> 3.15', '>= 3.15.2.317'
gem 'rsolr', '1.0.9'
gem 'rsolr-ext', '1.0.3'
gem 'capistrano'
gem 'rack-throttle', '0.3.0'
gem 'bcrypt-ruby', '~> 3.0.0' # To use ActiveModel has_secure_password
gem 'dalli'
gem 'delayed_job'
gem 'delayed_job_active_record'
gem 'daemons'
gem 'cobravsmongoose'
# gem 'bullet', group: [ :development, :test ]

group :test do
  gem "factory_girl_rails"
  gem "capybara"
  gem 'rspec'
  gem 'rspec-rails'
  gem 'shoulda-matchers', :require => false
  gem 'json_expressions'
  gem 'faker'
end

group :development do
  gem 'sextant'
  gem 'pry'
end

group :assets do
  gem 'sass-rails',   '~> 3.2.3'
  gem 'coffee-rails', '~> 3.2.1'
  gem 'uglifier', '>= 1.0.3'
end

Running $ bundle install I get this error:

An error occurred while installing libv8 (3.16.14.19), and Bundler cannot continue.
Make sure that `gem install libv8 -v '3.16.14.19' --source 'https://rubygems.org/'` succeeds before bundling.

Running $ gem install libv8 -v '3.16.14.19' --source 'https://rubygems.org/' I get this error:

ERROR:  Loading command: install (LoadError)
        cannot load such file -- openssl
ERROR:  While executing gem ... (NoMethodError)
    undefined method `invoke_with_build_args' for nil:NilClass

I tried following this post ruby 2.0 rails gem install error "cannot load such file -- openssl" .

This is the output when I try to reinstall openssl using 'rvm pkg install openssl' :

Beware, 'rvm pkg ...' is deprecated, read about the new autolibs feature: 'rvm help autolibs'.

Checking requirements for osx.
Certificates bundle '/usr/local/etc/openssl@1.1/cert.pem' is already up to date.
Requirements installation successful.
Fetching openssl-1.0.1i.tar.gz to /Users/username/.rvm/archives
Extracting openssl to /Users/username/.rvm/src/openssl-1.0.1i.....
Configuring openssl in /Users/username/.rvm/src/openssl-1.0.1i.......................
Compiling openssl in /Users/username/.rvm/src/openssl-1.0.1i..........................................................................................................................................................................|
Installing openssl to /Users/username/.rvm/usr..................................................................................................
Error running '__rvm_make install',
please read /Users/username/.rvm/log/1588596933/openssl_make.install.log

Please note that it's required to reinstall all rubies:

    rvm reinstall all --force

Updating openssl certificates....

The contents of /Users/username/.rvm/log/1588596933/openssl_make.install.log

installing man7/des_modes.7
installing man3/dh.3
installing man3/dsa.3
installing man3/ecdsa.3
installing man3/engine.3
installing man3/err.3
installing man3/evp.3
installing man3/hmac.3
/bin/sh: /Users/username/.rvm/usr/ssl/man/man3/hmac.3: Too many levels of symbolic links
make: *** [install_docs] Error 1
+ return 2

Even tried rm -rf /usr/local/ssl/man then rvm pkg install openssl and it produced the same error as above.

...Then I tried following this post: https://medium.com/cmthakur/fix-rvm-and-openssl-issue-2ef6ed47ebc2

$ brew uninstall — ignore-dependencies openssl
Error: No such keg: /usr/local/Cellar/—

$ brew install openssl
Updating Homebrew...
Warning: openssl@1.1 1.1.1g is already installed and up-to-date
To reinstall 1.1.1g, run `brew reinstall openssl@1.1`

$ brew reinstall openssl@1.1
==> Reinstalling openssl@1.1 
==> Downloading https://homebrew.bintray.com/bottles/openssl@1.1-1.1.1g.catalina.bottle.tar.gz
Already downloaded: /Users/alessandravertrees/Library/Caches/Homebrew/downloads/11b0b7c8d792b6abbcc8deefc5896b47e04c1ca541a607c8f73436bb55cf8fc0--openssl@1.1-1.1.1g.catalina.bottle.tar.gz
==> Pouring openssl@1.1-1.1.1g.catalina.bottle.tar.gz
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
  /usr/local/etc/openssl@1.1/certs

and run
  /usr/local/opt/openssl@1.1/bin/c_rehash

openssl@1.1 is keg-only, which means it was not symlinked into /usr/local,
because macOS provides LibreSSL.

If you need to have openssl@1.1 first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"' >> ~/.bash_profile

For compilers to find openssl@1.1 you may need to set:
  export LDFLAGS="-L/usr/local/opt/openssl@1.1/lib"
  export CPPFLAGS="-I/usr/local/opt/openssl@1.1/include"

For pkg-config to find openssl@1.1 you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/openssl@1.1/lib/pkgconfig"

==> Summary
🍺  /usr/local/Cellar/openssl@1.1/1.1.1g: 8,059 files, 18MB

$ export LDFLAGS=-L/usr/local/opt/openssl/lib
$ export CPPFLAGS=-I/usr/local/opt/openssl/include 
$ rvm cleanup all

Cleaning up rvm archives
Cleaning up rvm repos
Cleaning up rvm src
Cleaning up rvm log
Cleaning up rvm tmp
Cleaning up rvm gemsets
Cleaning up rvm links
Cleanup done.

$ rvm get head
Downloading https://get.rvm.io
No GPG software exists to validate rvm-installer, skipping.
Downloading https://github.com/rvm/rvm/archive/master.tar.gz
Upgrading the RVM installation in /Users/username/.rvm/
    RVM PATH line found in /Users/username/.mkshrc /Users/username/.profile /Users/username/.bashrc /Users/username/.zshrc.
    RVM sourcing line found in /Users/username/.profile /Users/username/.bash_profile /Users/username/.zlogin.
    Installing rvm gem in 3 gemsetsError running 'command gem install /Users/username/.rvm/gem-cache/rvm-1.11.3.9.gem --local --no-document',
please read /Users/username/.rvm/log/1588597867_ruby-2.2.4/gem.install.rvm->=1.11.3.9.log
Error running 'command gem install /Users/username/.rvm/gem-cache/rvm-1.11.3.9.gem --local --no-ri --no-rdoc',
please read /Users/username/.rvm/log/1588597870_ruby-2.0.0-p648/gem.install.rvm->=1.11.3.9.log
.
    Installing gem-wrappers gem in 3 gemsetsError running 'command gem install /Users/username/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-document',
please read /Users/username/.rvm/log/1588597873_ruby-2.2.4/gem.install.gem-wrappers->=1.4.0.log
Error running 'command gem install /Users/username/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-ri --no-rdoc',
please read /Users/username/.rvm/log/1588597874_ruby-2.0.0-p648/gem.install.gem-wrappers->=1.4.0.log
.
    Regenerating gem wrappers in 3 rubiesERROR:  While executing gem ... (Gem::CommandLineError)
    Unknown command wrappers
ERROR:  While executing gem ... (Gem::CommandLineError)
    Unknown command wrappers
ERROR:  While executing gem ... (Gem::CommandLineError)
    Unknown command wrappers
ERROR:  While executing gem ... (Gem::CommandLineError)
    Unknown command wrappers
.
Upgrade of RVM in /Users/username/.rvm/ is complete.

Thanks for installing RVM 🙏
Please consider donating to our open collective to help us maintain RVM.

👉  Donate: https://opencollective.com/rvm/donate


RVM reloaded!

Then output from reinstalling all rubies..

$ rvm reinstall all --force
ruby-2.5.7 - #removing rubies/ruby-2.5.7..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-2.5.7.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-2.5.7, this may take a while depending on your cpu(s)...
ruby-2.5.7 - #downloading ruby-2.5.7, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 13.1M  100 13.1M    0     0  2728k      0  0:00:04  0:00:04 --:--:-- 2906k
ruby-2.5.7 - #extracting ruby-2.5.7 to /Users/username/.rvm/src/ruby-2.5.7.....
ruby-2.5.7 - #configuring...................................................................
ruby-2.5.7 - #post-configuration.
ruby-2.5.7 - #compiling................................................................
ruby-2.5.7 - #installing.........
ruby-2.5.7 - #making binaries executable..
ruby-2.5.7 - #downloading rubygems-3.0.8
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100  867k  100  867k    0     0   960k      0 --:--:-- --:--:-- --:--:--  959k
No checksum for downloaded archive, recording checksum in user configuration.
ruby-2.5.7 - #extracting rubygems-3.0.8.....
ruby-2.5.7 - #removing old rubygems........
ruby-2.5.7 - #installing rubygems-3.0.8................................................................
ruby-2.5.7 - #gemset created /Users/username/.rvm/gems/ruby-2.5.7@global
ruby-2.5.7 - #importing gemset /Users/username/.rvm/gemsets/global.gems................................................................................
ruby-2.5.7 - #generating global wrappers................
ruby-2.5.7 - #gemset created /Users/username/.rvm/gems/ruby-2.5.7
ruby-2.5.7 - #importing gemsetfile /Users/username/.rvm/gemsets/default.gems evaluated to empty gem list
ruby-2.5.7 - #generating default wrappers................
ruby-2.5.7 - #adjusting #shebangs for (gem irb erb ri rdoc testrb rake).
Install of ruby-2.5.7 - #complete 
Ruby was built without documentation, to build it run: rvm docs generate-ri
Making gemset ruby-2.5.7 pristine..........................................................................
Making gemset ruby-2.5.7@global pristine.....................................................................
ruby-2.2.6 - #removing rubies/ruby-2.2.6..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-2.2.6.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Installing requirements for osx.
Updating system..........
Installing required packages: openssl.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-2.2.6, this may take a while depending on your cpu(s)...
ruby-2.2.6 - #downloading ruby-2.2.6, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 12.7M  100 12.7M    0     0  4016k      0  0:00:03  0:00:03 --:--:-- 4016k
ruby-2.2.6 - #extracting ruby-2.2.6 to /Users/username/.rvm/src/ruby-2.2.6.....
ruby-2.2.6 - #applying patch /Users/username/.rvm/patches/ruby/2.2.6/fix_installing_bundled_gems.patch.
ruby-2.2.6 - #configuring..........................................................
ruby-2.2.6 - #post-configuration.
ruby-2.2.6 - #compiling............................................................
ruby-2.2.6 - #installing..........
ruby-2.2.6 - #making binaries executable..
ruby-2.2.6 - #downloading rubygems-3.0.8
ruby-2.2.6 - #extracting rubygems-3.0.8......
ruby-2.2.6 - #removing old rubygems........
ruby-2.2.6 - #installing rubygems-3.0.8..
Error running 'env GEM_HOME=/Users/username/.rvm/gems/ruby-2.2.6@global GEM_PATH= /Users/username/.rvm/rubies/ruby-2.2.6/bin/ruby -d /Users/username/.rvm/src/rubygems-3.0.8/setup.rb --no-document',
please read /Users/username/.rvm/log/1588598906_ruby-2.2.6/rubygems.install.log
ruby-2.0.0-p648 - #removing rubies/ruby-2.0.0-p648..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-2.0.0-p648.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Installing requirements for osx.
Updating system..........
Installing required packages: openssl.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-2.0.0-p648, this may take a while depending on your cpu(s)...
ruby-2.0.0-p648 - #downloading ruby-2.0.0-p648, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 10.2M  100 10.2M    0     0  3138k      0  0:00:03  0:00:03 --:--:-- 3137k
ruby-2.0.0-p648 - #extracting ruby-2.0.0-p648 to /Users/username/.rvm/src/ruby-2.0.0-p648.....
ruby-2.0.0-p648 - #applying patch /Users/username/.rvm/patches/ruby/2.0.0/openssl3.patch.
ruby-2.0.0-p648 - #applying patch /Users/username/.rvm/patches/ruby/2.0.0/update-autoconf.patch.
ruby-2.0.0-p648 - #configuring.................................................
ruby-2.0.0-p648 - #post-configuration.
ruby-2.0.0-p648 - #compiling.......................................................................................................
ruby-2.0.0-p648 - #installing..............
ruby-2.0.0-p648 - #making binaries executable..
ruby-2.0.0-p648 - #downloading rubygems-3.0.8
ruby-2.0.0-p648 - #extracting rubygems-3.0.8......
ruby-2.0.0-p648 - #removing old rubygems........
ruby-2.0.0-p648 - #installing rubygems-3.0.8..
Error running 'env GEM_HOME=/Users/username/.rvm/gems/ruby-2.0.0-p648@global GEM_PATH= /Users/username/.rvm/rubies/ruby-2.0.0-p648/bin/ruby -d /Users/username/.rvm/src/rubygems-3.0.8/setup.rb --no-document',
please read /Users/username/.rvm/log/1588599320_ruby-2.0.0-p648/rubygems.install.log
ruby-1.9.3-p551 - #removing rubies/ruby-1.9.3-p551..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-1.9.3-p551.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Installing requirements for osx.
Updating system..........
Installing required packages: openssl.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-1.9.3-p551, this may take a while depending on your cpu(s)...
ruby-1.9.3-p551 - #downloading ruby-1.9.3-p551, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 9813k  100 9813k    0     0  1939k      0  0:00:05  0:00:05 --:--:-- 2100k
ruby-1.9.3-p551 - #extracting ruby-1.9.3-p551 to /Users/username/.rvm/src/ruby-1.9.3-p551.....
ruby-1.9.3-p551 - #applying patch /Users/username/.rvm/patches/ruby/GH-488.patch.
ruby-1.9.3-p551 - #applying patch /Users/username/.rvm/patches/ruby/1.9.3/CVE-2015-1855-p484.patch.
ruby-1.9.3-p551 - #applying patch /Users/username/.rvm/patches/ruby/1.9.3/update-autoconf.patch.
ruby-1.9.3-p551 - #applying patch /Users/username/.rvm/patches/ruby/1.9.3/openssl3.patch.
ruby-1.9.3-p551 - #configuring...............................................
ruby-1.9.3-p551 - #post-configuration.
ruby-1.9.3-p551 - #compiling.......................................................................................................................................
ruby-1.9.3-p551 - #installing...........
ruby-1.9.3-p551 - #making binaries executable..
ruby-1.9.3-p551 - #downloading rubygems-3.0.8
ruby-1.9.3-p551 - #extracting rubygems-3.0.8......
ruby-1.9.3-p551 - #removing old rubygems........
ruby-1.9.3-p551 - #installing rubygems-3.0.8..
Error running 'env GEM_HOME=/Users/username/.rvm/gems/ruby-1.9.3-p551@global GEM_PATH= /Users/username/.rvm/rubies/ruby-1.9.3-p551/bin/ruby -d /Users/username/.rvm/src/rubygems-3.0.8/setup.rb --no-document',
please read /Users/username/.rvm/log/1588599702_ruby-1.9.3-p551/rubygems.install.log
ruby-2.6.2 - #removing rubies/ruby-2.6.2..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-2.6.2.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-2.6.2, this may take a while depending on your cpu(s)...
ruby-2.6.2 - #downloading ruby-2.6.2, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 13.9M  100 13.9M    0     0  4075k      0  0:00:03  0:00:03 --:--:-- 4073k
ruby-2.6.2 - #extracting ruby-2.6.2 to /Users/username/.rvm/src/ruby-2.6.2.....
ruby-2.6.2 - #configuring.......................................................................
ruby-2.6.2 - #post-configuration.
ruby-2.6.2 - #compiling.....................................................................
ruby-2.6.2 - #installing...........
ruby-2.6.2 - #making binaries executable..
ruby-2.6.2 - #downloading rubygems-3.0.8
ruby-2.6.2 - #extracting rubygems-3.0.8......
ruby-2.6.2 - #removing old rubygems........
ruby-2.6.2 - #installing rubygems-3.0.8................................................................
ruby-2.6.2 - #gemset created /Users/username/.rvm/gems/ruby-2.6.2@global
ruby-2.6.2 - #importing gemset /Users/username/.rvm/gemsets/global.gems................................................................................
ruby-2.6.2 - #generating global wrappers................
ruby-2.6.2 - #gemset created /Users/username/.rvm/gems/ruby-2.6.2
ruby-2.6.2 - #importing gemsetfile /Users/username/.rvm/gemsets/default.gems evaluated to empty gem list
ruby-2.6.2 - #generating default wrappers................
ruby-2.6.2 - #adjusting #shebangs for (gem irb erb ri rdoc testrb rake).
Install of ruby-2.6.2 - #complete 
Ruby was built without documentation, to build it run: rvm docs generate-ri
Making gemset ruby-2.6.2 pristine.......................................................................
Making gemset ruby-2.6.2@global pristine.....................................................................
ruby-2.2.4 - #removing rubies/ruby-2.2.4..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-2.2.4.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Installing requirements for osx.
Updating system..........
Installing required packages: openssl.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-2.2.4, this may take a while depending on your cpu(s)...
ruby-2.2.4 - #downloading ruby-2.2.4, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 12.7M  100 12.7M    0     0  3509k      0  0:00:03  0:00:03 --:--:-- 3508k
ruby-2.2.4 - #extracting ruby-2.2.4 to /Users/username/.rvm/src/ruby-2.2.4.....
ruby-2.2.4 - #applying patch /Users/username/.rvm/patches/ruby/2.2.4/fix_installing_bundled_gems.patch.
ruby-2.2.4 - #applying patch /Users/username/.rvm/patches/ruby/2.2.4/openssl3.patch.
ruby-2.2.4 - #configuring..........................................................
ruby-2.2.4 - #post-configuration.
ruby-2.2.4 - #compiling..........................................................
ruby-2.2.4 - #installing..........
ruby-2.2.4 - #making binaries executable..
ruby-2.2.4 - #downloading rubygems-3.0.8
ruby-2.2.4 - #extracting rubygems-3.0.8......
ruby-2.2.4 - #removing old rubygems........
ruby-2.2.4 - #installing rubygems-3.0.8..
Error running 'env GEM_HOME=/Users/username/.rvm/gems/ruby-2.2.4@global GEM_PATH= /Users/username/.rvm/rubies/ruby-2.2.4/bin/ruby -d /Users/username/.rvm/src/rubygems-3.0.8/setup.rb --no-document',
please read /Users/username/.rvm/log/1588600494_ruby-2.2.4/rubygems.install.log
ruby-2.6.3 - #removing rubies/ruby-2.6.3..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.15/x86_64/ruby-2.6.3.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Updating certificates bundle '/usr/local/etc/openssl@1.1/cert.pem'
Requirements installation successful.
Installing Ruby from source to: /Users/username/.rvm/rubies/ruby-2.6.3, this may take a while depending on your cpu(s)...
ruby-2.6.3 - #downloading ruby-2.6.3, this may take a while depending on your connection...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 13.8M  100 13.8M    0     0  4267k      0  0:00:03  0:00:03 --:--:-- 4266k
ruby-2.6.3 - #extracting ruby-2.6.3 to /Users/username/.rvm/src/ruby-2.6.3.....
ruby-2.6.3 - #configuring.......................................................................
ruby-2.6.3 - #post-configuration.
ruby-2.6.3 - #compiling.....................................................................
ruby-2.6.3 - #installing...........
ruby-2.6.3 - #making binaries executable..
ruby-2.6.3 - #downloading rubygems-3.0.8
ruby-2.6.3 - #extracting rubygems-3.0.8......
ruby-2.6.3 - #removing old rubygems........
ruby-2.6.3 - #installing rubygems-3.0.8................................................................
ruby-2.6.3 - #gemset created /Users/username/.rvm/gems/ruby-2.6.3@global
ruby-2.6.3 - #importing gemset /Users/username/.rvm/gemsets/global.gems................................................................................
ruby-2.6.3 - #generating global wrappers................
ruby-2.6.3 - #gemset created /Users/username/.rvm/gems/ruby-2.6.3
ruby-2.6.3 - #importing gemsetfile /Users/username/.rvm/gemsets/default.gems evaluated to empty gem list
ruby-2.6.3 - #generating default wrappers................
ruby-2.6.3 - #adjusting #shebangs for (gem irb erb ri rdoc testrb rake).
Install of ruby-2.6.3 - #complete 
Ruby was built without documentation, to build it run: rvm docs generate-ri
Making gemset ruby-2.6.3 pristine.......................................................................................
Making gemset ruby-2.6.3@global pristine.....................................................................
Making gemset ruby-2.6.3@repo-api pristine............................................................................

Answer 1

I remember a time ago(2 months) I had issues with libv8. I can't quite remember what my issue was. I had a lot of these issues where gems didn't work quite right. Your answers are out there. Just rearrange your questions and focus on what is being said, I know it can get frustrating.

brew uninstall v8@3.15
brew uninstall v8
gem uninstall v8
gem uninstall libv8
brew install v8
brew link v8
gem install libv8 -v '13.16.14.19'
bundle config build.libv8 --with-system-v8

Check it out, it might be with some dependency that libv8 has on another gem. Good luck!