I preordered their latest book 'It Doesn't Have to Be Crazy at Work'.
A lot of their advice is aimed towards small teams. And often contrary to SV wisdom. We've built a few profitable businesses by following their advice without raising any funding.
The Four Steps to the Epiphany - Steve Blank. This is a MUST read. If you read nothing else, make it this book. Note that there is a 2nd Edition, which changes the title to "The Startup Owner's Manual". There is a lot of overlap in the content, but enough difference to justify reading both, IMO. I would start with the older one.
The Discipline of Market Leaders - Fred Wiersema, Michael Treacy - another crucially important book IMO. Does a great job of explaining how there are many different vectors along which you can compete, and explains how choosing which vector you're going to compete on is fundamental to defining your business and market.
The Art of the Start - Guy Kawasaki. Lots of good basics on startups
Differentiate or Die - Jack Trout, Steve Rivkin. - Title says it all.
It's Not The Big That Eat The Small, It's The Fast That Eat The Slow - Jason Jennings
The 22 Immutable Laws of Marketing - Jack Trout and Al Ries
Positioning: The Battle for Your Mind - Al Ries, Jack Trout, Philip Kotler
Crossing the Chasm - Geoffrey Moore
Mastering The Complex Sale - Jeff Thull - lays out an approach to selling that I believe is one of the best out there for enterprise / B2B. May not be as relevant for B2C or other approaches.
Exceptional Selling - Jeff Thull - more on Thull's selling approach.
The Prime Solution - Jeff Thull - and yet more still on Thull's selling approach.
The Innovator's Dilemma: When New Technologies Cause Great Firms to Fail - Clayton Christensen
Zero to One: Notes on Startups, or How to Build the Future - Peter Thiel, Blake Masters
How To Measure Anything - Douglas Hubbard. - Maybe one of the most important books I've ever read. The ideas in this book can apply in many domains, related to startups or otherwise. I can't recommend this one highly enough.
Repositioning: Marketing in an Era of Competition, Change and Crisis - Jack Trout, Steve Rivkin
Blue Ocean Strategy: How to Create Uncontested Market Space and Make the Competition Irrelevant - W. Chan Kim, Renée A. Mauborgne
Outside Innovation: How Your Customers Will Co-Design Your Company’s Future - Patricia Seybold
Never Split the Difference: Negotiating As If Your Life Depended On It - Chris Voss
The most interesting business book I've ever read was Creativity Inc, by Ed Catmull. He talks in depth about managing a business where creativity is the most important aspect.
The Start-up manual is good too, if a little drawn out.
That being said, a lot of people read it as a way to manipulate people. It shouldn't be read that way. Rather, if you follow the advice, it has to be genuine.
"Apple Computers is a famous example: it was founded by (mostly Republican) computer engineers who broke from IBM in Silicon Valley in the 1980s, forming little democratic circles of twenty to forty people with their laptops in each other's garages."
(Copy/pasted from web, but matches my memory of reading the book, so pretty sure it's accurate.)
Check this review of sorts by Jeff Atwood: https://blog.codinghorror.com/how-to-talk-to-human-beings/
It's probably out of date now but it inspired me to become an entrepreneur in 1994.
Also this is the best book I've ever read on negotiating by Chester Karass https://www.karrass.com/dr-chester-karrass
The readme includes a Google Doc summary by Joe Goldberg. It's like a greatest hits of greatest hits.
If you have build a business and want to do it even better, then “Principles” by Ray Dalio
Both are about mindset and worldview - something I am learning now is much more important in tools and marketing hacks and knowing what to do in every situation.
Hard thing about hard things
(Caution: It was written by gasp Peter Thiel.)
Kidding aside, I think it's a good one because it's a mix of analysis and history. Thiel had a unique vantage point, and he shares it well.
It also challenges you to be ambitious, which is becoming a rare sentiment.