Life is Too Short to Work with Assholes


Just thinking about the last one you worked with makes your stomach turn. The negative energy you felt in their presence is enough to make you want to throw up and remembering the damage they caused is something you shove so far back into your subconscious, you just hope it goes away.

Unfortunately there are assholes all around you. Enough of them that they find their way into companies, marriages, families, and friendships. A trait everyone can recognize that often goes unchecked for a long time until someone is willing to stand up and say enough, no more assholes.

Dealing with them in the start-up world sucks. They can tear a team apart and if they happen to invest, an entire company. Their quest for power is a zero sum game where their winning means someone else is losing. A game that works in the short term, but never in the long term.

Asshole is a subject so popular there are 154 million results on Google and in the business world interesting enough that Robert Sutton’s book, “The No Asshole Rule” became a best seller, everywhere.

What Motivates Them

“Real power can’t be given. It must be taken” ~ Godfather III

The simple answer is power. Driven by the belief that their winning is all that matters, they are willing to destroy everyone and everything around them to make their quest come true. Their lack of empathy comes through in how they speak, talk, and treat people.

At a more fundamental level, assholes engage in behaviors that intentionally cause emotional harm to others. In their mind, this is winning and the reaction you show or the anger you return only fuels their motivations. Your response is validation that yes, they are winning.

But where does this come from?


Fear of losing control. Fear of being rejected. Fear of opening their heart and being hurt. Fear that if they trust, they will be let down. Fear of the unknown.

Often anchored in past experiences that rocked their soul, assholes use intimidation and manipulation as a defense mechanism. They have a distorted perception that these are the only tools available to them when connecting with others. A false sense of reality they don’t realize until years down the road.

How To Detect Them

“Where there is fear, there is power” ~ unknown

Your gut instinct is the best indicator. Often pathological liars, assholes can be hard to detect, until they are faced with adversity. A loss of control quickly brings out their true self, at which point your detection is pointless because removing them from your company will be incredibly hard.

Outside of your gut instinct, here are a few signs I have found along the way.

  • They talk about themselves first, your problems second. Many assholes are narcissists. They do not have room in their attention span for the concerns of others.
  • The story they tell you is a far cry from what everyone else says. Even people you know will be hesitant to tell you what they experienced, out of fear of being a tattle tale. But when the story the asshole shares is very different from everyone else, there is something wrong.
  • Everything is perfect on the outside, but f’d up on the inside. They work really hard to make it appear as if everything is great, but behind closed doors they make everyone’s life hell.
  • You can’t find people in their past who will recommend them. Assholes either don’t have solid references or references willing to tell you the real truth. Few people will raise their hand and say “stay away at all costs.” And because you took them at face value, you failed to dig deep enough to find the truth.
  • In talking about their past they blame other people. The outcome was the result of mistakes everyone else made, while they avoid talking about their own mistakes and what they learned from them.
  • They dominate the conversation. Being in control is important to them so out talking you or over talking you is a sign that their concerns come before yours.
  • They don’t listen. Even in the interview you can tell they aren’t actively listening and aren’t thoughtful about your company. Instead they will be more focused on their role, salary, budget, and team available to do their job. A faint sign, you will find poor listening will lead to much deeper problems.

What makes this detection so hard is that assholes can be incredibly calculating. The web of manipulation they weave can be so thorough, you don’t even recognize it until you are wrapped up like a fly in a spider’s web.

What They Aren’t
Don’t be confused. People who are opinionated, direct, and assertive are not necessarily assholes. They are a rare breed of people who actually tell you what they think. Something the start-up world doesn’t have enough of.

Just because someone doesn’t agree with you, doesn’t mean they want to see you lose so they can win. Going by you because you go to slow is what successful people do. And since startups are a sink or swim world, you have to paddle fast.

But if you are wondering if someone is an asshole or just assertive, look into their heart.

Non assholes care. They want people around them to succeed. They are obsessed with the joy customers experience with their work. They have principles that don’t change. They want people to love them back. But above all else, when they finally trust you, they will make themselves vulnerable to you. Something assholes will never do.

How to Remove Them
Carefully and Quickly.

Assholes are vindictive and being told no, is not what they want to hear. What will amaze you is that when you do finally cut them out of your company or your life they will act surprised, as if you are mistreating them without any reference to the wake of people they left behind. They will feel wronged and threaten to take down what you have built.

If you founded a company with them, you have to start over or have very understanding investors. If they are an employee it will cost you severance and the threat of a lawsuit. If they are a friend or family member, you will lose people close to you that they managed to manipulate. If they are a customer, they will rant publicly about how poorly you treated them until you offer them something in return. If they are an investor, they aren’t going anywhere until you find a new investor to take them out.

Your best friend in parting ways are legal documents. Assuming you aren’t being physically threatened, finding a mutual understanding that is legally documented is super important. A third party, like your lawyer, can be incredibly helpful in this situation. Especially when the smell of you only further enrages the asshole.

Whatever route you take, do it quickly. Don’t let the feeling in your gut linger. Burying your head in the sand and ignoring the growing evidence is only a recipe for a massive problem down the road. Like a time bomb waiting to go off, the sooner you remove them, the easier it will be.

Navigating through assholes is another superhuman skill you need as an entrepreneur. Avoiding them is worth a lot because learning where they live, how they communicate, and the faint signs they give off will take some painful practice. If left undetected in your company, assholes will become some of your most expensive mistakes.

I wish they didn’t exist. It would make building a company just a little bit easier.

Image Credit: Chuck Evans via Creative Commons