From Amazon’s “2015 Letter to Shareholders“:
To invent you have to experiment, and if you know in advance that it’s going to work, it’s not an experiment. Most large organizations embrace the idea of invention, but are not willing to suffer the string of failed experiments necessary to get there.
Outsized returns often come from betting against conventional wisdom, and conventional wisdom is usually right. Given a ten percent chance of a 100 times payoff, you should take that bet every time. But you’re still going to be wrong nine times out of ten. We all know that if you swing for the fences, you’re going to strike out a lot, but you’re also going to hit some home runs.
The difference between baseball and business, however, is that baseball has a truncated outcome distribution. When you swing, no matter how well you connect with the ball, the most runs you can get is four. In business, every once in a while, when you step up to the plate, you can score 1,000 runs.
This long-tailed distribution of returns is why it’s important to be bold. Big winners pay for so many experiments.
Most if us have so little experience of asymmetric payoffs that we simply havent developed the System 1, “gut feel” for how to respond. It’s counterintuitive mostly because our normal intuitions are crap. In short, our gut has shit-for-brains.