Ask the Wizard

I received an email the other day asking what books I found useful as an entrepreneur. I realize this is a simple question, but I always find these kinds of things challenging because a) I don't read a lot of business books and b) I think too often people's lists are more about "look how smart I am" than "here are a couple things I found interesting".

I'll mention two books that I think are relevant to entrepreneurs and then one book where I'm making a real stretch, but I quote the book all the time so I might as well include it in the list.

The Places in Between. Summary: Non-Fiction, Scottish dude Rory Stewart walks across Afghanistan from Herat to Kabul in January 2002 in the middle of a war. Relevance to entrepreneurs: Very high. Starting a company is long on improvisation and short on thinking about the odds of success and that sums up this book. As the Afghanistan Security Service tells the author just days before he embarks on his journey - "You are the first tourist in Afghanistan. It is mid-winter - there are three meters of snow on the high passes, there are wolves, and this is a war. You will die, I can guarantee". Taking his journey one step at a time, and always always making the best out of his current situation, The Places in Between is a great parable for entrepreneurs who must approach business the same way - without a security net. Additionally, no matter how hard it gets for you, and it might get pretty hard, you will be able to look back on this book and think "I've got nothing on this guy".

Fooled by Randomness OR The Black Swan. Summary: Philosophy of Randomness. Author Nassim Taleb essentially believes that business people (and the media and historians and everybody else) oversimplify rational explanations of past data, and underestimate the prevalence of unexplainable randomness in that data, which leads them to underestimate the chances of outlying events, which he calls Black Swans. Relevance to entrepreneurs: Very High. Learn to think about potential outcomes more probabilistically and learn to stop thinking that you see simple patterns where luck, chance and other factors probably played roles. Fooled by Randomness is the quicker read. Tip of the hat to FeedBurner investor Brad Feld who recommended Fooled by Randomness to me about a year ago (i think, maybe it was two years ago. Boy, it's all blurring together).

Conversations with my Agent Summary: Mostly fiction. Author Rob Long describes the conversations he has with his Agent as he leaves his highly successful role as writer and coproducer of Cheers and begins to create a new show from scratch. Relevance to entrepreneurs: I'm stretching here, but work with me. The beauty of being reminded that we live in a 'what have you done for me lately' environment in which the people who've been around the block a few times probably aren't as dumb and random as they seem is a great read for entrepreneurs that can't understand why VC's say up when you think down, and why customers say black when you think white.