I will say this for starters. I thought that college was actually one of the most open environments I've ever been in. Moreso than pre-college education. Moreso than working at a VC-backed startups. Moreso than working in corporate America. Probably the only time I had significantly more freedom was taking some time off between jobs.
When I see statements like, "Failure is punished instead of seen as a learning opportunity" -- I see immaturity. He punishes himself for failure. I've seen it as a learning opportunity since junior high at least (I think this something athletics really instils in children, although certainly not exclusive to athletics).
In any case, he sounds like a friend, and I don't want to rant on a friend, especially if he's not here to defend himself. I look forward to what he can do over the years. Maybe he'll prove me wrong.