If you are interested in the Truffle backend in JRuby, these videos explain how it all works. It's less theory, and more practical explanation about writing a language using Truffle. Maybe you'd like to write your own Truffle language! A lot of the concepts explained in the video are used almost exactly the same in Ruby.
You don't need any expert knowledge of VMs or compilers to understand them. https://www.youtube.com/watch?v=N_sOxGkZfTg https://www.youtube.com/watch?v=EXzaBTLlS9I Chris