What I took away as the core idea of this book is the following: People should be exposed to the risks of their actions. The world would be a better place for it.
Nassim Taleb draws several related conclusions from this core idea - for example, a disdain for theorists/intellectuals in comparison to people actually applying their knowledge and doing things in the real world. More on that later.
The idea that it is beneficial for everyone to have skin in the game is a good one. An excellent example of what happens when people don't have skin in the game is what Nassim Taleb calls the "Bob Rubin trade."
The Bob Rubin Trade
Robert Rubin is a former Secretary of the United States Treasury who collected more than $120 million in compensation from Citibank in the decade preceding the banking crash of 2008. We now know that the collapse occurred due to the "accumulation of hidden and asymmetric risks in the system" by bankers and people like Bob Rubin. But when the crash happened, and Citibank became insolvent, taxpayer money bailed out Citibank - not Bob Rubin. He collected profits when things were going well, but all of the risk was transferred onto taxpayers. Bob Rubin had no "skin in the game" since he was not exposed to the risks of his actions. Taleb's argument, which I agree with, is that people who have "skin in the game" will probably make better decisions, and those who don't will be wiped out - rightfully so.
Whether or not you agree with this concept, it is compelling - and presenting compelling ideas is what Taleb does very well.
What I Didn't Like
Now that I've presented the good, the bad: The book is not well structured, and the writing feels like rambling. After a strong start explaining this concept, it felt like the book kept spinning around this same (good!) point over and over for far too long. I'm aware that's to be expected for books centered on one idea, but the combination of poor structure, somewhat arrogant tone, and stream-of-consciousness writing made finishing the book feel like it wasn't worth it. I put it down about a third of the way through.
Additionally, I don't think all of Taleb's ideas hold water. For example, theoretical scientists, despite not being exposed to the "real world," have made significant contributions to society.
Do I Recommend This Book: No
Given that I could not finish this book, I would not recommend it to anyone else. It presents interesting ideas, but getting through the book feels like work, rather than an enjoyable experience. Nevertheless, I see why some people really like his books, and I plan on checking out some of Taleb's earlier work in the future.