Three Qualities Every CEO Should Have

These Questions originally appeared on Quora - the knowledge sharing network where compelling questions are answered by people with unique insights.

Answers by Tony Stubblebine, behavior designer, startup founder, CEO of, on Quora.

A: Yes, I think there are three. But I want to give a caveat about the point of being a CEO. It's kind of a crummy job unless you have some greater mission. That's putting it lightly.
It's hard. You work a lot.

Plus, you end up being isolated from your team because your experience is different than theirs. You're the boss and there's always at least one thing you can't tell them. The most obvious example of that is if you are going to fire someone or have fired someone. That's a traumatic event that you can't talk about honestly with most of your coworkers.

Some people become CEOs because they can't help themselves. They're just wired to think more ambition is good, but there's no real purpose to it. I think those people are wasting their lives.

#1. Mission.

Given all the above, you have to have a mission that you're trying to achieve. You really need to believe that what you're doing is making the world better or it just isn't worthwhile.

Having a mission makes you better at your job too. But I think that's secondary.

#2. Persistence

Most of work is failure. Ideally, not many people see it. But your job is to be constantly improving yourself, the products and the team.

You're in a job that's basically impossible to do well. Most of your decisions come with a lot of uncertainty.

So, when you make mistakes, you need to be able to learn and try again.

A lot of times nothing seems to be working but you know you need to find an answer eventually. So you need to not let go.

#3. Be the heat seeking missile

There's a motto that I tell myself all the time, "progress is progress." I'm not sure if it works with other people, but the key corollary is most things aren't progress.

Before you're a CEO you can get away with merely getting your work done. But as the CEO you're responsible for making sure all work matters.

Most people don't notice when their work doesn't matter (I find this infuriating, but it's obviously true). It's fine for work to fail. But not noticing is a serious problem because then you can't adjust.

So, the key quality that I try to hone for myself is in getting better at making sure the work we do pans out.

I have a little anecdote about this. A CEO friend from me presented this problem.

His investor had introduced him to a top engineer. The engineer was supposedly the #12 best Rails engineer in the world (I don't know how you'd measure that). My CEO friend managed to hire this engineer and was initially very happy. Mission accomplished, right?

But later, the CEO told me that this engineer didn't like the product and never checked in any code. What should this CEO do?

And that's my point, that hiring a top engineer isn't progress. Progress is when you hire an engineer that gets stuff done. That's an important distinction and I fall into traps like that all the time.


A:There's two things that I think young entrepreneurs should hear more often. To me, they're both about getting unstuck and making sure you actually start a company.

Starting companies are hard, everyone knows that. But they're also very rewarding. you grow a ton. You get to make an impact on the world. Both of these are more valuable than the money you're making or giving up.

So, the two things that I'd lead with are:

#1. You don't need funding.

Just because you read about 22-year-olds getting into YCombinator or getting venture funding doesn't mean you need to go that route.

This is important to point out because not everyone is going to find investors. So don't let this stop you.

In fact, don't let anything stop you. Your job is to find creative ways to get around hurdles. Not having money is a tiny hurdle.

So, first of all, if you want to know if funding is the right path for you, there's a simple way to find out. Try to get it. If you don't get it then adjust to be a bootstrapper.

In many ways, bootstrapping a company is easier. Bootstrapping you forces you to:
  • Build something smaller because you have fewer resources.
  • Build something that makes money right away. Getting paid clarifies a lot of decisions.

Most people with investment money spend a lot of time in fantasy land because they are building something that's too big and that isn't getting any feedback. You avoid both of these problems by bootstrapping.

My first company was bootstrapped. I was 27 when I started it. I'm not sure if you'd consider that young.

I coded the first version of the product myself and hustled for customers. I did unrelated consulting on the side for six months. This paid my bills. Then for three years we also did white-label consulting based on the product we built. That paid even more bills until we had enough volume business to stop doing custom work.

MailChimp was built this way. So was 37Signals. There's a really great conference where bootstrapped software companies gather called
. I'd recommend attending just for the inspirational benefit. There are way more successful, privately owned software companies than you realize. Of course, a lot of people who go down this road do end up getting investors at some point.
. UnderArmour was originally a guy selling clothes out of his trunk. That was 1995.
. I find that most people who are frustrated that they can't raise money are suffering from one of two things:
  • They don't have the skills to build something themselves. I think these people are suffering from too much entitlement. People aren't going to give you money if you have no skills. Dude.
  • They don't actually want to be entrepreneurs. What they really want is to be rich and famous. The gritty part about starting small and building something up over time doesn't appeal.
#2. You don't need to start a startup right now
Every now and then I'll see a young entrepreneur say that they feel like they're behind and have no way of catching up. Yeah, if you're 26 and haven't started a successful company then you're behind where Mark Zuckerberg was. If that's how you feel, I'd strongly consider seeing a therapist instead. There's a hole that you're trying to fill through entrepreneurship. Don't start a company to impress other people. Do it when you just have some idea that you need to prove to the world. It's ok if you're not ready to start a company right now. Here are the things that I did before getting funded for the first time:
  • Fake started two companies in classic wantrepreneur fashion. I talked up the ideas for months but never did anything with them.
  • Got a degree in Computer Science.
  • Worked for three companies and two startups over the course of seven years.
  • Wrote a book on programming.
  • Bootstrapped a company for four years.

* Built a prototype and took that to a rich friend who I'd know for six years. I'd worked with him and he'd watched my growth. He invested based on a coffee meeting. But it took me 15 years of work in order to put myself in a position to get that meeting.

Like a lot of my advice, these two things boil down to "do the work." If your time frame is 20 or 30 years, then entrepreneurship is pretty straight forward.


These questions originally appeared on Quora. - the knowledge sharing network where compelling questions are answered by people with unique insights. You can follow Quora on Twitter, Facebook, and Google+. More questions:​