"The Virtue of Selfishness" "Capitalism: The Unknown Ideal" "Philosophy: Who Needs It" "Introduction to Objectivist Epistemology" All by Ayn Rand. Whether you end up agreeing with her or not, she will definitely will make you think.
He had to overcome a lot of bad thinking habits to gain a genuine understanding of Objectivism and he is in a good position to help others get past those roadblocks.
Objectivism: The Philosophy of Ayn Rand is useful to help you integrate Rand's philosophy into a mental hierarchy, and his courses Understanding Objectivism and Objectivism Through Induction are useful to help you prove Objectivism to yourself, so you can see how Rand's philosophy really is connected to reality and pertains to your life.