There's a Teach me to code screencast which may be helpful 
- http://teachmetocode.com/screencasts/shoulda-on-rails/
And some basic documentation on Rails wiki 
- http://wiki.rubyonrails.org/testing/shoulda

Some of the official documentation here:
https://github.com/thoughtbot/shoulda#readme
https://github.com/thoughtbot/shoulda-context#readme
https://github.com/thoughtbot/shoulda-matchers#readme

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