diff --git a/Guardfile b/Guardfile
new file mode 100644
index 0000000..ae6decc
--- /dev/null
+++ b/Guardfile
@@ -0,0 +1,20 @@
+# A sample Guardfile
+# More info at https://github.com/guard/guard#readme
+
+guard 'rspec', :version => 2 do
+  watch(%r{^spec/.+_spec\.rb$})
+  watch(%r{^lib/(.+)\.rb$})     { |m| "spec/lib/#{m[1]}_spec.rb" }
+  watch('spec/spec_helper.rb')  { "spec" }
+
+  # Rails example
+  watch(%r{^spec/.+_spec\.rb$})
+  watch(%r{^app/(.+)\.rb$})                           { |m| "spec/#{m[1]}_spec.rb" }
+  watch(%r{^lib/(.+)\.rb$})                           { |m| "spec/lib/#{m[1]}_spec.rb" }
+  watch(%r{^app/controllers/(.+)_(controller)\.rb$})  { |m| ["spec/routing/#{m[1]}_routing_spec.rb", "spec/#{m[2]}s/#{m[1]}_#{m[2]}_spec.rb", "spec/acceptance/#{m[1]}_spec.rb"] }
+  watch(%r{^spec/support/(.+)\.rb$})                  { "spec" }
+  watch('spec/spec_helper.rb')                        { "spec" }
+  watch('config/routes.rb')                           { "spec/routing" }
+  watch('app/controllers/application_controller.rb')  { "spec/controllers" }
+  # Capybara request specs
+  watch(%r{^app/views/(.+)/.*\.(erb|haml)$})          { |m| "spec/requests/#{m[1]}_spec.rb" }
+end
diff --git a/spec/lib/penchant_spec.rb b/spec/lib/penchant_spec.rb
new file mode 100644
index 0000000..e69de29
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
new file mode 100644
index 0000000..e69de29
diff --git a/template/script/initialize-environment b/template/script/initialize-environment
index a702166..222c8f1 100755
--- a/template/script/initialize-environment
+++ b/template/script/initialize-environment
@@ -22,8 +22,14 @@ end
 puts "Installing git hooks"
 system %{script/install-git-hooks}
 
-puts "Trying to run rake bootstrap..."
-system %{rake bootstrap}
+bundle = File.file?('Gemfile') ? 'bundle exec' : ''
+
+command = [ bundle, 'rake', '-s', '-T', 'bootstrap' ]
+
+if !(%x{#{command.join(' ')}}).empty?
+  puts "Trying to run rake bootstrap..."
+  system %{#{bundle} rake bootstrap}
+end
 
 puts "Done!"