Skin in the Game


The Book in Summary

  • This book is about risk and simplicity in a complicated world. Taleb highlights an imbalance between those who are making decisions and those who are paying the price for them.
  • It explores: 1) The reliability of knowledge, both practical and scientific, 2) risk imbalances, 3) information and transparency, and 4) rationality in complex systems.
  • It highlights the principal-agent problem and how it feeds off unnecessary complications, risk transferal and smart people who think they know what they're doing.


  • It's a pretty heavy book in terms of philosophical ideas but Taleb breaks them down in a "no-bullshit" manner. I really loved the use of ancient quotes and stories to explain modern problems.  

How I discovered it

My Top Quotes

  • Beware of the person who gives advice, telling you that a certain action on your part is “good for you” while it is also good for him, while the harm to you doesn’t directly affect him
  • He speaks of “equality of races” and “economic equality,” but never goes out drinking with a minority cab driver
  • Products or companies that bear the owner’s name convey very valuable messages. They are shouting that they have something to lose
  • If your private life conflicts with your intellectual opinion, it cancels your intellectual ideas, not your private life.


  • This book helped me understand a link between my love extreme sports and business. In both settings, a person willing to own their risks and there is something really pure in that. It also helps to drive performance with acute and tactile feedback (read broken bones and bankruptcy).
  • In my role I am regularly involved in investment fundraising, so one of my biggest links for this book was on the agency problem in finance industry settings. It helped explain why most of the conversations I have are about mitigating (their) risk.
  • Something I have been thinking about for a while is the rise in online courses, advisors and how-to videos. Taleb cautions to avoid taking advice from someone who gives advice for a living, unless there is a penalty for their advice.
  • I'm usually not impressed when someone has a great track record of safe-bets. Now I know why.