Skin In The Game

Sticking with the Antifragile theme, Taleb (and Gordon Livingston) write that honor flows from demonstrating courage when exposed to risk due to one’s beliefs. Taleb uses the example of enduring ridicule, and financial risk, for being true to his beliefs. 

Last summer, I listened to elites hammer on about the underclass not having skin in the game. This discussion seemed to lack justice but I wasn’t able to put my finger on an exact reason.

Having worked alongside the wealthy, I have experience with the problems of the rich. My move to the US gave me a chance to dig deeper into tax policy and I’ll be sharing some observations about that in future articles.

At the top of society, what does an honest person risk?

  • Size of main residence
  • Frequency, location and duration of vacations 
  • Number of years until retirement
  • Proportion of personal budget dedicated to luxury spending
  • Amount of capital passed to the next generation

Facing the above doesn’t require courage – no wonder extreme activities become popular in societies with wide income differentials.


In Taleb’s worldview, meaning comes from exercising courage with regard to one’s beliefs. I tend to derive meaning from the pursuit of excellence, working on my goals and meeting my obligations to my family. There’s not much personal risk in the way I roll through life, but it seems to work for me.

I enjoyed the Antifragile book, so I’ve been considering how I might be fooling myself. I’ve come up with a few areas.

As a 4th generation, first born, white male… the world has been skewed in my favor since birth. Listening, to my peers complain about the burdens of sharing society with their fellow citizens, demonstrates an ignorance of my reality. Seeing older versions of myself complain offends something inside me – my time in Asia taught me that I rarely have anything to complain about.

There is a disconnect between my reality and what the public is told about people like me. My effective (US) tax rate is similar to what I paid in Hong Kong. Having lived in Europe, Oceania and Asia – America is a low-cost, and very attractive, place to live and work.

Taleb makes the point that seeking to change the human condition is folly and warns against seeking to remove greed. He advises regulation to protect our societies from the effects of greed. Examples would be getting rid of banks that are too big to fail and applying criminal sanctions for white collar criminals. There have been a lot of examples in the news recently. HSBC banking drug cartels and Barclays fixing global interest rates. If a small institution took these actions then their directors would be going to jail, or at least losing their banking license.

Remember that we only see a portion of the corruption in our societies.

  • What do the financial scandals tell us about that society?
  • What does the USADA report tell us about endurance sport?
  • What lessons can we learn from these real-life dramas to make better decisions in our own lives?
  • When faced with an ethical choice, do we take the money or remain true to ourselves? 
  • Is it possible to do both?

I’ve spent a lot of time considering the above and my latest book shared a road map for how I live.

Before we publish on Amazon, my editor asked me to include the human side of how I arrived at my framework. Over the next few months, I’ll be sharing the stories that created my way of living.

Two Virtues

Last week a friend sent me an article about preparing heirs and I asked myself, ‘what virtues do I want to pass to my kids?’

Kindness and honesty immediately came to mind.

Why do these stand out and how does my life demonstrate these traits to my kids?

I have very few regrets in my life but those that stand out are due to a lack of kindness at the end of relationships. The other errors that I’ve made had to do with excess drinking.

I can’t teach my kids about how to treat ex-girlfriends nicely anymore. However, I have better avenues for leading by example. How do I treat the most important person in their life, their mother.

The other area, that’s often overlooked, is how I treat people that can be mistreated with little personal downside, service people and strangers. There’s no better prevention for entitlement than working on humility with strangers. This trait has brought goodness, and good business, to my life.

Thursday’s blog will focus on having skin in the game and touches on the decisions that have brought me the most enduring satisfaction. As you can tell from my most recent book, I’ve received psychic benefit from not “taking the money.” This trait runs deeper than finance and has been tested many different ways.

Rather than tell my kids “don’t lie” I’ve been implanting a mantra of “it’s better to tell the truth.”

Cycling gave me an opportunity to explain why and I’m waiting for when they ask me about my own life.

What am I teaching my family by the way I live my life?