From most to least recently read, highly recommended books have a (+1) at the start.
(+1) Crossing the Chasm
Superior tech -> Strategic advantage -> “Whole product” -> Brand/reputation
I probably need to read this again, I didn’t quite understand how the model fits for products targeting existing markets. I liked the brief mention of intuition vs data in decision making, wish the author spent more time there, as I have some thoughts of my own brewing about what I like to call “cargo cult data driven decision making”.
(+1) Hackers & Painters: Big Ideas from the Computer Age
Paul Graham is good at writing. His takes on strict/dynamic typing won’t age well. He articulates really well why business-driven engineering produces shitty results, though I wish more of the book was about that rather than cryptic Lisp evangelism.
Obnoxiously terse. Very much “preaching to the choir”. I enjoyed it but I have similar philosophies around work/business.
The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It
Basically “don’t be a craftsman”. Good if your only reasons for going into business are to make money and dominate others.
Designing Data Intensive Applications
Second read-through of this. A good overview of various topics around backend engineering, though I wish it was more opinionated.
When to Rob a Bank: …And 131 More Warped Suggestions and Well-Intended Rants
Fun beach reading.
The Gervais Principle repackaged for bitter software nerds. I wish I could buy The Gervais Principle as a paperback.