From what I read in The Dream Machine, Shannon sounded like a super cool guy. I love the fact that he talked down the overhype of his own field: https://news.ycombinator.com/item?id=41972922
That was an interesting (and short!) read. Most of what he wrote is applicable to ML/AI today. A direct link to the pdf for those too lazy to click twice: https://ieeexplore.ieee.org/stamp/stamp.jsp?arnumber=1056774
I'm still reading it, but apparently he stopped talking to his own mother forever after she refused to give him a cookie intended for guests.