Here’s To The Crazy Ones

Steve Jobs said,

Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules… You can quote them, disagree with them, glorify or vilify them, but the only thing you can’t do is ignore them because they change things… they push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.

People in general are risk averse.  If you don’t look like what the heuristics or spreadsheet says then you are easy to pass over.  The people that pass you over answer to a boss.  It’s easy for them to justify the pass.  One friend of mine said when selling to corporates, find out what the boss wants.  Sell to those needs and the underlings will buy.

It’s not enough to wear rebel clothing, grow some facial hair, get a tattoo.  What Jobs is talking about is a presence and a state of mind.  It’s a way of looking at the world.  We are conditioned to stay in the box.  Tribes impart norms on us that keep us in the box.

Ben Horowitz in his book The Hard Thing About Hard Things talks about hiring executives.  On page 125, he has a bullet point, “Looking for someone out of central casting”.  He goes on to say, “If I had followed this path I would never have hired Mark Cranney and you probably would not be reading this now.”   Cranney was not an Ivy League grad but went to Southern Utah.  He wasn’t a runway model but an average looking human.  Without him as head of sales, Horowitz company fails.

People want someone out of central casting because it makes them look good immediately.  But, central casting doesn’t send a lot of round pegs in square holes.

Academically, this book proves mathematically why allocating some of your hires as a “risky hire” is a good idea.  It helps a company capture randomness. There are great gains in randomness.  Great losses too, but we aren’t in this game to be standard are we?

Sometimes, it pays to be George Costanza and do the opposite.  If your company is full of risky hires maybe the thing to do is get someone who isn’t to add them to the blend.

One thing I have learned about engineers is this, if it wasn’t built “here”-wherever here might be-it sucks.  My partner Kenny told me about this ethos in HFT firms.  They’d see all kinds of things from the outside and the engineers would rip it up and tear it apart and say they could build it better inside the company.  I think the same can be said for a lot of things.  When you don’t come from central casting, it’s easy to dismiss you.

The deeper I get into the entrepreneurial ecosystem and the deeper I get into much of the operations within it, the more I find people want central casting.  Yet, they crave the other.  They feel like because they work in an innovative industry, they are doing the other.  Many of the leading lights in entrepreneurship are in a box.  They struggle to get out of it.