Don't Work With Assholes

There's a wealth of literature out there about this, but it can never be said enough. Too many people work with assholes.

You see them everywhere.

The cafe owner that takes a shortcut by hiring an asshole barista? The barista plays shit music at your cafe and nobody wants to go there.

The startup founder who values talent over attitude? The asshole co-founder or top exec, no matter how good they are at their jobs, is going to screw you over.

Eventually you realize that you're losing money and that nobody wants to talk to you at industry events anymore. Or perhaps investors or future team members take you aside to say they want to be a part of your dream team, but… that guy is an asshole.

Assholes don't inspire trust.

Assholes can sometimes be nice, too.

People often make the mistake of assuming that the opposite of an asshole is a push-over. It is not. The opposite of an asshole is a decent business-person or partner who brings net positives to the table. An asshole, no matter how occasionally nice, perhaps to certain people, or to most people, has certain characteristics which breed mistrust and disdain.

At my first startup, I worked with a guy who was a really nice person, and very good at his job-to me.

I was new to the scene. I had no idea.

He had ideas, he got things done, he was a good person-to me.

But he was not a good person to people who could not give him something.

There will always be people like that.

I'm talking to a handful of investors at the moment and what I do for each one is to see who has worked with said people before. I call them, no matter how tenuous the link, and say: "What do you think of ____?"

You don't really have to get more specific than that.

You can, of course, to clarify some of the assumptions that people might have made, or to get more details on deals gone sour, etc, so that you can make up your own mind.

But I've found most often that if I am going to be met with silence or awkwardness or worse, with hemming and hawing which can seem unjustified, it's a red flag for me.

This applies to people I hire and to people I date, too.

You need to be sure that this person doesn't kick old ladies or torture pets when you're not looking. A good way is to see how they treat waiters and how they respond to the homeless or the poor.

I don't need you to be a bleeding heart old lady hugger (please don't), but life's too short for anything that isn't "fuck yes, yes and yes".

No amount of money is ever worth it. That's not idealistic-it's the most practical advice I was ever given.