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.

and

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. 

A moment of Solitude

One thing which happens to all CEOs is the number of voices coming at them every day increases.

Their team gives them feedback. So does their board of directors. Other investors weigh in regularly. There are advisors which have opinions as well.

The voices get louder. A connected CEO can fill his/her days with these voices.

To say being a startup CEO is a tough job is quite an understatement.

It happens to VCs as well but at a different level. The voices come at us all the time. Signals and conversations all day long. Every day. Every week.

In addition to these conversations and meetings we read blogs and tweets with suggestions, tips, wrongs and rights. every day. Every week.

One of the most effective things to do in a sea filled with voices is to just stop.

Take some time and get into your own head.

Take comfort in the solitude. In the quiet. It could be an hour. Or two. Or a day. Or two.

In an age of open office collaborative spaces, non stop meetings, hallway discussions, texts, coffee catch ups, we can often miss the creative juices and insights from time alone.

So if children are able to live with mistakes and even failing, why does it drive us crazy? So many parents have said to me, “I can’t stand to see my child unhappy.” If you can’t stand to see your child unhappy, you are in the wrong business. The small challenges that start in infancy (the first whimper that doesn’t bring you running) present the opportunity for “successful failures,” that is, failures your child can live with and grow from. To rush in too quickly, to shield them, to deprive them of those challenges is to deprive them of the tools they will need to handle the inevitable, difficult, challenging and sometimes devastating demands of life.