The
View from Initialized

Should you be the CEO?

Just because co-CEO worked for Google doesn’t mean it will for your startup

Picture this… it’s 2010, and me and my co-founder are pitching on Sand Hill Road. We’re sitting in the offices of Andreessen Horowitz, pitching Marc Andreessen and Ben Horowitz.

We thought it was going fun, just like the others. Ben turns to us and asks, “Who’s the CEO?” I looked at my co-founder Sachin, he looked at me, we said both. Guess what? It was the wrong answer. The meeting might as well have ended at that moment.


The most legendary duo that can and did pull off saying “both” to the co-CEO question is Larry Page and Sergei Brin, the founders of Google. You could say that we thought we could be just like that dynamic duo. What was good enough for Google surely could be good enough for us, right?

Whoa, Whoa, no. Look, we had a good hockey stick graph. We had software we had built that we were proud of. But most people are not Google at their series A. I know we weren’t. Ben Horowitz actually wrote a long form article about this in 2013. He said:

“Shared command always seems really attractive to the people at the top of the organization, like the CEO and the board. ‘We have two world-class people. This gives us the best of both worlds. We shouldn’t get caught up in the conventions of years past. We’re all adults, we can get along.’ It looks much less attractive to those who do all the work in the organization. To them it looks like frustration, chaos, and delay.”

That’s the real reason why co-CEO doesn’t work. It’s bad for founders and bad for everyone else.

Everything takes longer. So you have a hard decision to make. You have two co-CEOs. You have to wait for the co-CEOs to agree. That makes every decision you have to make much longer. It becomes life or death at that point. You slow down so much, that your startup will die.

Image for post
Don’t let your startup die because you can’t decide.

Back to sitting in that Andreessen Horowitz conference room. It was 2010. How did I find myself in this position? We didn’t know who the CEO was yet, and yet we were here talking to venture capitalists about raising millions of dollars.


I didn’t think being CEO mattered. And later I discussed it with my co-founder after our series A and he became the CEO. And if I’m being honest with you, I regret that. You may not be interested in authority, but authority is interested in you.

When you’re talking about who’s CEO or trying to divide the pie, there are moments when you and your co-founders are aligned, and there are moments when you aren’t. Moments where you have to divide the pie are the latter. And the best you can do is make sure that you self-advocate. Try to think through what you need.

Image for post
Grab the slice that’s best for you AND the company.

I’m absolutely glad I worked on Posterous and I’m glad I did it with my co-founder at that time. But, it took me too long in my career to realize that I needed to be CEO. And I needed to be CEO for the same reason I wanted to be a founder. If it was broken, I needed to be able to fix it.

If things are broken, are you okay with someone else being in charge of fixing it? If you’re going to be incredibly frustrated that you don’t have the authority and can’t fix it, then maybe you do need to be CEO. And that’s the thing I wish I could have told myself at that moment.

I didn’t know myself well enough. And it took 20 years of my career to realize it. Don’t make my mistake here. It doesn’t have to be an ego thing. It’s just something that you need in your life. It’s okay to need that. It’s okay to need agency. And that was one of the big things I made a mistake on.


I actually really wanted to keep coding. I had to decide whether I wanted to be CEO or if I could keep designing and writing code and shipping product. Writing code and shipping product, those felt really good to me. In the moment, I chose sticking with the things that made me feel good.

One of the things that did give me pause that you should consider if you’re thinking about becoming CEO is that it’s very different from being an individual contributor or director manager of a particular part of the product.

It becomes extremely important, right after product market fit. Early on, it’s all hands on deck, get a product or service off the ground. Later there are a few things that only the CEO can do. And you’ve got to ask yourself, are you willing to drop everything else just to do this?

Can you convince people to follow you? Can you hire, can you manage, can you fundraise and manage investors? Can you drive the vision of the company? Most importantly, can you be the magic that brings all of those things together, to build a great product or service?

Being CEO is a very specific skillset. And unless you are signing up to do those things, and do them to the best of your ability, don’t. Being CEO is not for everyone. But if you want to be CEO, those are the things you need to do. The other jobs are incredibly important, too, but this role is a singular one.

Image for post
A CEO needs to lead a company in concert. Is that you?

Every situation is very different. For some of you, you may never want to be CEO, and that’s fine. For others, you may love doing another thing, but you may need to become CEO to steer the ship. And others still, you knew the day you quit your job that you absolutely have to get that authority. Only you can decide for yourself.

Don’t make my mistakes, don’t delude yourself about whether or not you should be CEO. If you know, you know. Then, it’s on you to acquire the skills, and manifest it. I know you can do it.


Thanks for reading! To watch my full episodes that go into detail about these ideas — and more — head over to my YouTube channel.