The Best of Charlie Munger - A great collection of articles and transcripts from Charlie Munger, vice chairman of Berkshire Hathaway. Seems particularly relevant to Less Wrong as an example of an individual using applied rationality and an interest in cognitive biases (even before they had a name) in the pursuit of systematized winning.
Note: I'm still quite confused with how to think about subjective experience and sleeping beauty-type scenarios. I don't give this scenario much weight, but find it interesting to think about:
Ordinarily, your future is void of any future-self brain states following your death, so the probability of your subjective experience following a path that leads to death in the near future is low (assuming youth, good health, avoidance of risky sports/habits, etc). However, after signing up for cryonics, you open up new potential future-self brain states that follow...
The Bobiverse Series by Dennis E. Taylor
A fun book series with good pacing that explores a lot of interesting ideas (cryonics, mind uploading, AI, etc). Highly recommended.