Hacker News Books

* Fooled By Randomness (NN Taleb): Taleb is a complicated personality, but this book gave me a heuristic for thinking about long-tails and uncertain events that I could never have derived myself from a probability textbook.

* Designing Data Intensive Applications (M Kleppmann): Provided a first-principles approach for thinking about the design of modern large-scale data infrastructure. It's not just about assembling different technologies -- there are principles behind how data moves and transforms that transcend current technology, and DDIA is an articulation of those principles. After reading this, I began to notice general patterns in data infrastructure, which helped me quickly grasp how new technologies worked. (most are variations on the same principles)

* Introduction to Statistical Learning (James et al) and Applied Predictive Modeling (Kuhn et al). These two books gave me a grand sweep of predictive modeling methods pre-deep learning, methods which continue to be useful and applicable to a wider variety of problem contexts than AI/Deep Learning. (neural networks aren't appropriate for huge classes of problems)

* High Output Management (A Grove): oft-recommended book by former Intel CEO Andy Grove on how middle management in large corporations actually works, from promotions to meetings (as a unit of work). This was my guide to interpreting my experiences when I joined a large corporation and boy was it accurate. It gave me a language and a framework for thinking about what was happening around me. I heard this was 1 of 2 books Tobi Luetke read to understand management when he went from being a technical person to CEO of Shopify. (the other book being Cialdini's Influence). Hard Things about Hard Things (B Horowitz) is a different take that is also worth a read to understand the hidden--but intentional--managerial design of a modern tech company. These some of the very few books written by practitioners--rather than management gurus--that I've found to track pretty closely with my own real life experiences.