set the console to pry

template.rb

initializer 'myveryfirstinitializer.rb', <<-CODE
  Rails.application.configure do
    console do
      require "pry"
      config.console = Pry

      require "awesomecompany"
    end
  end
CODE

gem "pry"

file 'app/models/awesomecompany.rb', <<-CODE
  class Awesomecompany
    class << self
      def readme
        binding.pry
        puts "readme"
      end

      def pagerduty
      end

      def contributing
      end

      def help
      end
    end
  end
CODE

after_bundle do
  git :init
  git add: "."
  git commit: %Q{ -m 'Initial commit' }
end

rails new example -m template.rb --api
cd example
bin/rails c
> Awesomecompany.readme