That sounds like perfectionism run amok, to me. He is maybe thinking that "first" is who he is, and he's doing whatever he needs to do in order to protect that part of his identity.

Involve him in some activities that he WILL fail at-- preferably those that others will be noticeable superior at, too.

MAKE him get used to "losing."

Along with that, involve him in some activities which HAVE no win/lose component, and for which that kind of thing has some negative peer/social pressures.

Schrödinger's cat walks into a bar. And doesn't.