Why You Can’t Be Friends with Your Co-Founders

Startup co-founders often describe their relationships as “being like a marriage.” They spend countless hours together working, eating meals, and traveling. They learn to deal with each other’s weird eccentricities. They learn to be comfortable around each other in ways normal friends aren’t. And, just like in marriages, they get into big fights they’re forced to resolve because their lives and wellbeing are intimately entwined. Given such close, personal, longterm relationships, you’d think finding a co-founder among your friends would be a good strategy. But choosing a friend as a co-founder is a bad idea. Do you know why?

Before I explain why you shouldn’t look for co-founders among your friends, I feel obligated to admit that my co-founder of nearly 15 years in three separate companies began as my childhood best friend. We met when we were 10 years old, and we didn’t launch our first company together until we were in our early 20s.

I realize I seem like a hypocrite for not following my own advice, but the reverse is closer to the truth. I used to think building companies with my best friend was what enabled us to succeed, but it was the opposite. It was something we had to overcome. In fact, here are four of the biggest challenges we faced as friends building businesses together.

Challenge #1: You’ll have too much fun being friends

My initial hint that being best friends and co-founders wasn’t a good combination came within the first year of working on our first company together. Don’t get me wrong — I enjoyed being co-founders with my best friend, but that was also part of the problem. We had trouble separating the “work time” from the “hanging out” time. After growing up together, watching movies, playing video games, and getting into general mischief of the teenage boy variety, it was difficult to “turn off” those tendencies in favor of working. Why spend hours doing dull sales prospecting work or building developer APIs when you could spend the same hours goofing around with your BFF? In other words, our first few years working together didn’t result in as much work as it should have, and, because of that, our first attempt at launching a company didn’t get far.

Challenge #2: You’re not as investable as you think you are

Once my friend and I realized we needed to get more serious about business if we hoped to build anything of consequence, our second attempt to launch a startup went smoother in terms of product and customers. However, we struggled to raise funding, and we couldn’t figure out why. Our metrics were good, our growth was strong, we were in a “hot” industry, and we felt like our team had the right combination of credentials and complimentary skills to impress investors.

Unfortunately, the investors didn’t agree. We’d stroll into pitch meetings believing we’d impress VCs with our company, and then our strong founding team, with its long history of being close friends, would seal the deal. After all, how could investors not feel great about investing in a team that had been collaborating since before puberty? Hadn’t we proven a willingness to stick together through exactly the kinds of tough times we were guaranteed to face while building a startup?

But the investors didn’t see things the same way. Our decade of prior friendship created a big gap in the proof we needed to demonstrate our potential for success. For investors, successfully finding co-founders reveals important aspects of a team’s hiring, management, and operational capabilities. Can they find other highly qualified people to work with? Can they learn to communicate well with those people? Can they develop trust? And so on.

In contrast, as best friends prior to becoming co-founders, we didn’t have to “talent search.” We didn’t have to learn how to communicate. And we didn’t have to learn how to trust. It’s not that we weren’t capable of those things, but being friends before being co-founders meant we had to work harder to prove it.

Challenge #3: You’ll think too much alike

Despite our pre-existing friendship being a flaw in the eyes of investors, my co-founder and I spent years positioning our longtime friendship as a selling point. This inability to identify the problem was a symptom of being close friends.

Having grown up together, my co-founder and I saw the world in similar ways. While this made us compatible as friends, it created challenges in our ability to think critically about the problems we were facing. Rather than leverage different perspectives and life experiences to troubleshoot our problems, we tended to have more of a “we’re right and they’re just idiots” mentality. As you can probably guess, that wasn’t a helpful way of seeing the world. We were our own echo chamber.

This problem extended beyond fundraising to every other aspect of the business — sales, hiring, product roadmap, marketing, and so on. For example, imagine trying to get useful feedback on a new advertising campaign from someone who thinks like you. In some ways, it’s like asking for feedback from yourself.

Challenge #4: You’ll struggle to add new team members

Eventually, my co-founder and I did learn to overcome the challenges I’ve described. We raised significant capital for our third company and grew our user base so large we got beyond our ability to run the company ourselves. We needed to add senior management.

In a startup, senior managers — C-suite execs and VPs — aren’t much different from co-founders. We’d be spending long hours together, working hard together, traveling together, eating together, arguing together, and making tough decisions together. But, as co-founders who’d, by that time, spent 20 years as best friends, we struggled to bring new partners into our working relationship. Everyone, no matter how qualified for the job, struggled to overcome the gap in familiarity that gets established during two decades of friendship.

Yes, we did hire people. And yes, we all worked well together and accomplished great things. But, when I look back on those times, I think about how, no matter the team members we added, my co-founder and I always separated ourselves from everyone else. In some ways, I suppose that’s natural. It was, after all, our company. But it might have also limited our potential.

As with every decision in life, we’ll never know whether the outcomes would have been different had we taken another path. And, to be fair, the path we chose wasn’t terrible. After all, I got to spend 15 years (and counting!) working side-by-side with my best friend. How many people can say that? But building companies with friends has drawbacks, too, and you should know what they are before you do it. If nothing else, you’ll at least be better prepared than we were to deal with the challenges.

Aaron Dinin teaches entrepreneurship at Duke University. A version of this article originally appeared in Medium, where he frequently posts about startups, sales, and marketing. For more from Aaron, you can also follow him on Twitter.