Around nine years ago I read Nicholas Taleb’s seminal texts The Black Swan (2007) and Fooled by Randomness (2001) and I loved them both. For venture investors everywhere The Black Swan suddenly provided a framework and lingua franca for understanding our business – betting on extreme outcomes that have a low probability of occurring, and perhaps more subtly for those working in this world, an understanding role of chance is critical to distinguishing talent from luck (although we all need luck).

But for me the books were about more than these two key takeaways, they were also an amusingly written philosophy of life and a celebration of avoiding the herd mentality and thinking differently.

One small part of that which has stayed with me is Taleb’s oft repeated advice “Don’t run for trains”. I like this advice because running for trains is stressful and it seems to me that we often take on that stress without really thinking it through. There’s a problem, however, which is that sometimes when we miss trains it makes us late, and it’s rude to be late.

When I was riding my bike to work this morning, Taleb’s advice “Don’t run for trains” popped into my mind. That’s happened a fair few times over the years and as I’ve done before I rehearsed the argument made in the previous paragraph. Then, rather than return to thinking about my day as usually would, I pondered the advice a little longer. I wanted to resolve the dichotomy between the good and the bad sides of “not running for trains” and maybe get a better idea of what Taleb was getting at.

For me the answer is that Taleb’s point is to avoid over-valuing short term gains. If you run and get the train it feels good for a short while, but you will have forgotten it before long, so why put yourself through it. Better surely to apply yourself to something that will deliver value over the longer term. This chimes with Taleb’s long term investment strategy. In his books he repeatedly shows his disdain for investors who chase short term gains (he calls them “yield hogs”) whilst not understanding their long term risks. Moreover, running for trains is often a frenzied activity of the type that with hindsight turns out to be ill-advised.

In the startup world, examples of “running for trains” mostly involve chasing short term growth at the expense of long term value:

  • Selling a poor quality product or service which undermines the brand
  • Putting so much advertising on a web page that it destroys the customer experience
  • Tricking people onto a website with a misleading promise



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