Date your potential cofounder

Following the launch, everything started going to shit, and a huge number of challenges to the success of the company had arisen. The biggest of these were the lack of traction from launch, that we had lost the faith of our journalists, and because there were communication issues between Nathan (my co-founder) and I. This combination also killed our motivation.

As a result, I made a carefully thought out decision to shutdown the company, and return as much money as we had left (about 40%) to the investors. Nathan believed the best thing to do would be to pivot our company, and so I agreed to step down to allow him do that. After some work, he agreed that it was best to shut it down (hence the email above), and we are currently going through the steps of winding down the company, and returning the remaining money to investors.

I met Paul and Nathan while they were doing YC, and we dined and talked a couple times. While their original idea for a commenting system for newspapers was not good, they changed their idea quickly to NewsTilt, and seemed to be on their way to making stuff happen. I was rooting for them, as I liked the both of them, and they seemed like pretty good guys.

However, I had no idea about any of these problems between them, and I was surprised as anyone. I appreciate the candor that Paul has in writing it, and it’s often valuable to know why you failed, than to look at why people have succeeded. This is because I think we all often fail in the much the same way, but our successes have more to do with the specific markets, situational opportunities, and problem domains that we’re in.

One of the big lesson I got out of reading it is it matters who your cofounder is and how you and your cofounder interact. It’s been said time and time again. It matters who your cofounder is. Think of it as getting married. And herein lies a problem: most of us try to pick a cofounder before we know what we want and need. Knowing how to pick a cofounder (and for that matter your significant other), requires two things in my mind.

One, knowing yourself, what you value, what you need from another, and what you have to give in return. And two, being able to read others and figure out what motivates them. Both are soft-skills that are a far cry from technical matters, and hence hard to convey in words. It’s only won through being in lots of different social situations, and meeting people from all walks of life and backgrounds. Working with all sorts of personalities in close proximity will bring out these traits and you’ll have to deal with them.

And for any one specific person, you won’t know until you’ve worked with them for a while. Given that, if you wouldn’t marry someone you’ve never dated, you shouldn’t be cofounders with someone you’ve never worked with.

And it may not be someone who you’ve been friends with for a long time. Those that have never worked together or fought together (with each other or along side each other) have never really tested their friendship. That said, not all friendships need to be tested in this way–only those that you intend to go to war with or start a startup with[1]. 

I started my startup career with a long-time friend. We’d known each other since sixth grade, and always had a tight bond and connection. However, doing a startup together was the wrong thing to do. Our motivations weren’t aligned, our appetite for risk wasn’t the same, and our skills didn’t complement each other. We’re still good friends, but it’s highly unlikely we’ll ever work together again.

Oddly enough, the guy that did end up being my cofounder was someone I had ended up being roommates with first through craigslist. We didn’t decide to start working together until 2 months after being roommates. We ‘dated’ by working together for a couple weeks first on something, and it ends up we’re quite compatible. As with all relationships, you don’t know where it’s going to go, but for now, we’re both cautiously optimistic and constantly work at having a better relationship with each other. 

I hope you take your time looking around for cofounders that don’t only have the skills, but someone who can communicate with you, and also is honest and has integrity. That last part is quite important.

To quote Warren Buffet about hiring, but I think it applies equally to cofounders:

“Somebody once said that in looking for people to hire, you look for three qualities: integrity, intelligence, and energy. And if they don’t have the first, the other two will kill you. You think about it; it’s true. If you hire somebody without the first, you really want them to be dumb and lazy.” – Warren Buffett

And people show their integrity when they’re faced with difficult decisions and difficult situations. Do they do what’s right? Or do they do what’s easy? Listen for stories from when your potential cofounder faced these situations and see what they did or didn’t do, and you can probably get a pretty good idea of how they’ll behave when you’re in the trenches with them.

So date your potential cofounder. Do small projects together. Build a twitter clone. Build something that can be done in a weekend or a week. Talk to them about their past. How have they failed? What did they do when they failed? Can they communicate to you their thoughts clearly? Do they listen and process what you have to say? The list goes on, but hopefully, it’ll give you a good start.

[1] I’m not trying to imply starting a startup is like going to war. Only that the trust in the guy that’s suppose to have your back in war is the same trust you need in doing a startup.



2 thoughts on “Date your potential cofounder

  1. hey Wil! its my first time reading one of ur blogs. I liked the post a lot! Thanks for the insight! =)- your former camper

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