I think he's trying to say:
In '85 - Jobs couldn't really do any succession planning / future products / directions / etc... So he didn't set anything up for apple (unless you count the fact that long term they bought NeXT etc etc)
In '08 - Jobs will be sorely missed. The WWJD (What would Jobs Do?) question will be asked around apple for years to come
Wasn't NeXT set up by Steve Jobs in 1985, around the time he was removed from Apple?