Cut him some slack. He's just trying to do the manly thing of teaching what he knows best, the way he was taught it, which of course was the best way
Especially if he felt that he "earned" his rise up to the really good gear by using semi-good stuff first.
I went through a phase of that when I had rock climbed a couple of years - long enough to have learned a lot of stuff and identify myself intensely as a rock climber, not long enough to realize there were other ways of doing it. I was pretty insufferable 
Clipless is not rocket science. You'll be fine!
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett