The
View from Initialized

Co-Founder Conflict & Why I Quit my Startup

How you can avoid the #1 killer of early stage startups

In the weeks before I resigned from my last startup I couldn’t sleep; I couldn’t eat; and my heart rate felt pegged at 120. I had reached a point where I couldn’t agree with my co-founder over the future of the company. I had to step away from the startup for which I shed blood, sweat, and tears. I didn’t want to do it, but I had reached a point, physically and mentally, where I couldn’t handle the stress anymore. This was me at the end of 2010.

Every co-founder situation is different, but one common problem that keeps popping up revolves around how founders engage in conflict — either not enough or far too much. Co-founder disputes are the number one early startup killer, but it doesn’t have to be that way.

How success masks co-founder conflict

When things are going up and to the right, it’s easy to miss things going wrong underneath you. My first startup Posterous grew 10x yearly and became a top 200 site on the web in just about two years. By the end of 2010, our growth had flatlined. And when the business needed me and my co-founder the most, we couldn’t get along. The reality is you can’t count on good times forever. For every startup out there, no matter how big or how small you are, winter is coming.

Too little conflict

My co-founder and I were friends for years. We met in college, but we learned the hard way that history is not enough. You’ve got to keep the lines of communication open just like any relationship. You know what happened? We had too little conflict.

With hindsight, I now realize my rift with my co-founder was entirely preventable. We stopped spending time together because we were avoiding conflict. It was a double-whammy. Right at the moment when we needed to come together, we hadn’t resolved our conflicts for so long that our relationship went out the door too. I had skipped the hard work of embracing conflict and resolving it.

Why did this happen? Well, everyone knows great startups have great co-founder relationships — that’s what I wanted. But what I mistook for the appearance of good was actually avoidant. I was more focused on making it seem like we were good co-founders — so much so that I failed to actually create that situation. And so much of life as a founder is actually about avoiding this kind of situation. Don’t make it look like a good startup or a good co-founder relationship. Instead, spend time actually making it a good startup and actually a good co-founder relationship. And it was my fault. Rather than take the harder road of standing up for what I knew, whether it was about product, personnel or strategy, I buckled; I self-abandoned. I sacrificed what I knew to be right at the altar of this idea that good co-founders don’t fight, and as I did that, my resentment grew.

I think of our brains as sort of separate parts. There’s a narrative prefrontal cortex that is trying to explain everything — what you might view as conscious — and then there’s the rest of your brain —  nonverbal but very much a part of how we think. Those parts speak to us through emotions and feelings. My conscious narrative wanted to keep up the fiction that we were good co-founders for one another. While deep down, large parts of me knew it just wasn’t true. When that tension became too great, it felt like the nonverbal parts of me started going on strike. That’s why I had that super high pulse and wasn’t able to eat, wasn’t able to sleep… I was at war with myself. I was at my breaking point. If you haven’t spent time with your co-founder outside of work, ask yourself why. Actually, are you at a point like that right now? Do you try to keep your interactions at a minimum? That’s a tell. It’s an indicator that something isn’t working.

My first executive coach Cameron Yarbrough of Torch taught me that this is usually the moment the four horsemen of the apocalypse show up: defensiveness, criticism, contempt and stonewalling. When psychologist John Gottman, who’s the author of the four horsemen concept, identifies those behaviors in marital relationships, he’s able to predict relationship failure with amazing accuracy. And the same thing holds true for co-founders. If too little conflict is your problem, here’s what you need to do. If you don’t agree on something, don’t leave the room until you have a resolution. If an hour is not enough, cancel your weekend; go on a hike, even go camping; get out of dodge; have a retreat and decide to do it on the spot. Get back on the same page. Make time for this. Cancel other things — those other things can wait. Some of the best billion dollar company founders I know did exactly that. Those founders are now billionaires many times over. Learn how to communicate exactly what you’re feeling and in the right way. Feedback is actually really key in these scenarios. And that’s one of those things that I didn’t do. You need to err on the side of giving more feedback.

Embrace conflict instead of abandoning yourself. I’ve always valued harmony in my interactions with everyone I’ve worked with, but with time — and again, sometimes the hard way — I’ve learned that you can’t sacrifice what you know to be right in order to get that harmony early. You’ve got to fight. Don’t swallow your words. If you have a point, make sure you are heard.

Too much conflict

On the other hand, there are lots and lots of co-founder situations where there is way too much conflict. Some of you might be saying, “Too little conflict, how is that a problem? We’re fighting absolutely all the time.” Trust me. As often as conflict avoidance happens, it can be as common to have way too much conflict.

Here’s what it feels like when there’s too much conflict on your team:

  • It can be hard to really make decisions. Every proposal or communication ends up being viewed through the lens of “how will the different factions view this.”
  • You might find yourself horsetrading, e.g., I can have this if you can have that.
  • Meetings just end up long and acrimonious.
  • Team members get paralyzed over small decisions, sometimes even just trying to figure out what venue to bring these issues to [in order] to make that decision. And even after a decision is made, the decision is retread and questioned over and over again.
  • Old arguments are renewed, and outcomes of those prior decisions are used as justifications in new conflicts.

The sheer fact that you might be able to identify factions in the first place is a clear warning sign. The worst is if you find yourself blending unrelated decisions due to different wants and desires of different sets of people on the team. If you start seeing that, you’re probably in a bad spot.

When founders are in a situation where they’re fighting about everything all the time, it usually means that their individual roles are not well-defined enough. People actually might not know who’s in charge of what and why.

Here’s what you have to do. Make a list of all the areas needed for your business then figure out who’s best at each part and assign one person to it. At Y Combinator, I remember it was the founders of Heroku who famously did this. They made a list of all the different tasks that the company did, and for every single one, they found exactly one owner, a founder or executive, whose ass was on the line to deliver that thing — that’s accountability.

This is useful for two reasons:

  1. It makes it clear who to talk to. The process becomes obvious to everyone because it’s written down; everyone can see it. The owner makes sure to collect feedback before they make their decision. That’s one of the key parts of being an owner.
  2. It means you can move fast. There’s no question at that point who makes the call. The owner makes the call. And when the call is made, everyone agrees to disagree and commit. That way, you’re not fighting the same battles over and over, and you’re not waiting weeks, months or sometimes, years for a decision. Finally, if you find that your co-founder conflicts are so fundamental [and] you really can’t move forward, you have to start listening.

The loudest person in the room shouldn’t necessarily and automatically be the one who wins. This is actually a conflict avoidance of a different stripe, one that doesn’t give any space to the competing ideas at all. Listen first, and let the other side know you hear them. One of the best ways to think about this is actually a steel man hypothesis: if you can actually listen to the other person and repeat back the strongest version of their argument, that’s a steel man instead of the straw man.

I saw a fantastic thread by Stripe product manager, Shreyas Doshi. [To paraphrase,] he says listening is hard because we fear being wrong; we desire validation; we have a lack of curiosity and an urge to impress; and we have a feeling of superiority.

Below is a clip from the movie “The Darkest Hour.” Do you find yourself interrupting people like this?

(The Darkest Hour, 2017; Paramount. Time: 1:50 - 2:20)

Shreyas points out that even if we don’t speak to people the way Winston Churchill does, we often think that way in our heads. Our internal monologue interrupts what people are saying with what we are thinking. I have to admit I’m terrible at this. I’m often so busy trying to figure out what I want to say that I fail to fully internalize and be present around what is being said by others, especially when those things are counter to my beliefs or convictions I might have. Those are the hardest moments, but those are often the most important moments for you to really, really listen. Some of you watching this have actually been through all of these exercises and more.

Get help

For those of you who feel like you’re coming to the end of your rope, even for the people who are in the middle of it, I have one final piece of advice: get help! It really helps to get outside of your head and talk through what you’re seeing with all kinds of people — other founders and friends, executive coaches or whomever you trust who you can talk to. Don’t be afraid to bring in the pros.

In fact, I recommend people bring them in early. Be open to getting professional help either individually to help you respond to the ongoing conflict or as a group — similar to how a marriage counselor can save a marriage. Hire an exec coach. I can’t recommend it enough for founders, especially when a company killing conflict is on the line. If you’re looking for help, I recommend checking out Torch.io, which is the number one marketplace for coaches that we funded at Initialized. Torch was founded by my first exec coach Cameron Yarbrough. He helped me through so many moments just like the ones we’ve been talking about today.

Revisit: Reprogram your mind with exec coaching – interview with Cameron Yarbrough

Athletes have coaches and trainers who help them get to peak performance. How is knowledge work any different? It can be just as demanding. One thing we got to talk about though is cost. A lot of founders, especially early on, are freaked out about it. Well, of course you shouldn’t go crazy with this, and you should find coaches that are appropriate for your stage of company. You should also know that making the wrong decisions will cost you your company and your vested equity. This is not a place to cheap out. Third-party help when you’re at an intractable state can literally save your startup.

Finally, involve your board, your investors, your advisors, your closest founder friends… You can’t do this alone. When you’re going through this stuff, I know for a fact there’s an embarrassment. You don’t want people to know. You shouldn’t broadcast this to the world, but you do need your most trusted people close to you. They can help you see things through a new perspective and just help you through this really tough time.

Co-founder conflict remains the number one killer of startups. I really hope this was a helpful guide for you as you navigate these tough times. I want you to know if this is your problem right now, you’re not alone. So many people — pretty much all founders I’ve ever talked to — have some form of this.

Know someone who can benefit from my advice? Be sure to check out my YouTube channel and subscribe.