Antifragile, by Nassim Nicholas Taleb, presents a truly unique viewpoint about the world. While there are many things here that are far fetched, there is far more that is very sound in its analysis. Even if you disagree with everything in it, this book’s usefulness, in the form of working theories about how to survive in the world, will prove itself very apparent.

Next, by Michael Lewis, is probably my least favorite book my him. Regardless, I’m convinced that he’s in his own league, so Next is still an excellent book.

Behind the Cloud, by Marc Benioff, is his own story about how Salesforce became one of the first software-as-a-subscription services. While it honestly sometimes felt like another marketing ploy for Salesforce, there were many nuggets of wisdom to take out of it.

The Everything Store, by Brad Stone, is a critical and beginning-to-end (well, middle, since they still labor on) look at how Amazon came to be. Unlike many books about technology founders, Stone does not descend into “hero worship,” and instead tries to stick to cold, hard facts.

The New New Thing, by Michael Lewis, is a pseudo biography of Jim Clark, meant to be introspective of the modern day tech industry. While it was written nearly twenty years ago, much of the culture that was unearthed in the 1990s still remains in Silicon Valley, and the attitude of a man who founded three separate billion dollar companies is something to pay very close attention to.

Never Split the Difference, by Chris Voss, is a book about how to negotiate. As opposed to theoreticians in a classroom, Chris Voss spent a great part of his life negotiating in the real world, and with the highest stakes imaginable, as an FBI hostage negotiator.

The topic of this summary in quotes is Skin In the Game. The book’s central argument is that people who don’t participate in both the downside and upside of something don’t know what they are talking about. Simply put, if you haven’t been chastised for failure in the real world and promoted for excellence in that same real world, then you will fail to actually know how the real world works.