Books:
What the Dormouse Said - an intimate account of the personalities and social forces that were running through the counter culture tech scene in the Bay area that produced ARPAnet and its successors.
Blocksize Wars - another account of the personalities, debates and egos that occured around the BCash/segwit time period . Written in a unique style; it doesn't read at all like an "airport business book". My favorite bitcoin book
On the topic of books, The Cuckoo’s Egg, by Cliff Stoll, is a classic. Still a great story, probably best if your old enough to recall technology of that era.
I recently ran across this course (licensed CC) that works from the book to provide an infosec crash course: https://chrissanders.org/training/cuckoosegg/
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