I can't imagine myself not being "with it" and having some knowledge about current technology.. Do you think any of the early modern Internet pioneers know about LLMs? (Besides John Nagle)? Or does the brain biologically give up on processing new information?
I met and worked with alot of the early internet pioneers and they were some of the most clever and insightful people that I've ever met. I assure you that barring a serious medical condition they all maintain at least a basic awareness about the state of computing.
To make a blanket anecdotal statement, personally they seem to be fairly with it on new technologies. Not the most in depth understanding but definitely above the average person.