Also seems this post is in direct response to a question he received at his Q/A. A link to the blog post about his talk was posted by another user just recently (can't seem to find the user atm), http://www.rubyrailways.com/dhh-fuck-the-real-world/
Not sure how I feel about the "Nice guys finish last" bullet, but it was very interesting to read about all his success at a young age.
Edit: He gets very repetitive and sounds quite out of touch as you read. Regardless, I still enjoyed reading about the drive he had when he was young. Must have been hard to teach a student who makes more than you do ;)