Are we ready to work with the crazy ones?

We all talk about how many of the best founders are a eccentric, passionate, highly intelligent, opinionated and willing to take a chance they are wrong. 

We want to be around those people and help them with their dreams – whether we are employees or investors. 

We don’t want to work or back clones or incremental ideas. 

We want people daring enough to change the world and put a dent in the universe. That’s why we often toast the crazy ones

Two gems amongst many from this mighty fine summary of Peter Thiels CS183 come to mind as I think about this topic.

PayPal’s founding team was six people. Four of them were born outside of the United States. Five of them were 23 or younger. Four of them built bombs when they were in high school. (Your lecturer was not among them.) Two of these bombmakers did so in communist countries: Max in the Soviet Union, Yu Pan in China. This was not what people normally did in those countries at that time.


We are biased toward the democratic/republican side of the spectrum. That’s what we’re used to from civics classes. But the truth is that startups and founders lean toward the dictatorial side because that structure works better for startups. It is more tyrant than mob because it should be. In some sense, startups can’t be democracies because none are. None are because it doesn’t work. If you try to submit everything to voting processes when you’re trying to do something new, you end up with bad, lowest common denominator type results.

But pure dictatorship is unideal because you can’t attract anyone to come work for you. Other people want some power and control too. So the best arrangement is a quasi-mythological structure where you have a king-like founder who can do more than in a democratic ruler but who remains far from all-powerful.

Somehow the very thing that attracts employees and investors to creative, brilliant founders is same thing which challenges founders keeping their teams/investors engaged and supportive through all the many ups and downs.

It’s usually some combination of heartfelt inspiration, loyalty, friendship and a belief that the founder led company is the best of them all.