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Business with friends, it’s complicated

Friends should never work together. How many times do we hear that? But who would you want to build a startup with, if not your friends? Who else would you want to spend so much time with? Who else could you convince to do something so crazy?

Ten years ago I had an idea and I was lucky enough to convince two talented guys, Alexander Aghassipour and Morten Primdahl—two of my friends—to start Zendesk with me. (It was an idea for software, not a company, back then. And it was not called Zendesk either; it went by a bunch of truly terrible names.)

I met both Alex and Morten through work. Alex and I both had startups and we socialized together in Copenhagen’s small startup scene. I met Morten after my startup blew up, when I worked for a large corporation and he began working for me as an intern. We had no idea what we were in for when we started working together.

At the beginning, we liked hanging out. But the fun part didn’t last forever. The long hours spent crammed inside Alex’s loft began to wear us down.

Heightening the tension was the fact that we were all working for no money. Nothing like a little financial stress to bring out the best in people! This came to a boiling point when we were trying to raise money.

In late 2008, after some disappointing fundraising mishaps, Charles River Ventures (CRV) sent a term sheet. CRV was a solid firm with a good track record and I thought it was a huge victory. Morten and Alex were not as pleased.

Alex was deeply concerned that I wasn’t looking at it critically, that I was moving too fast. “You are being a 12-year-old,” he told me.

I accused him of getting carried away by his anxieties. I told him he was thinking small, and not being visionary. We were not playing nicely. The fights brewed and I couldn’t take it anymore. Fully frustrated, one day I stormed out yelling, “Let’s forget all about all this shit!”

Obviously that was ridiculous. We couldn’t just forget about it. By that point we had a business to run and decisions to make. The next day I showed up for work, as did Morten and Alex, and we did what had to get done to take care of the company and our customers.

During this time I felt as if Alex, Morten and I, friends and co-founders, were more like parents engaged in an ongoing disagreement—not speaking during the day, sending snarky emails, walking out angry, and lying on opposite sides of the bed at night. That was the awkward undercurrent, but we didn’t let that get in the way of what was most important. Our priority remained ensuring that our kid felt good even if we didn’t. We were united by our baby, even if we didn’t like parenting with one another.

During this time I felt as if Alex, Morten and I, friends and co-founders, were more like parents engaged in an ongoing disagreement.

A good friendship and strong partnership is very powerful for a founding team, but it can also make things harder. You have to work in agreement and nobody has the final vote. Truly, it’s a miracle that we remained together when everything was an unknown and there was no stability and no salary. It’s lucky that we all loved our baby equally, which kept us from giving up.

But we also loved and needed each other. Because of our different personalities and approaches, we were able to contribute different pieces that were all of value. In a way we were like three necessary legs of tripod—dependent on one another and only strong if we were together. I think the fact that we had a history, that we saw something unique in one another, and that we were friends, somehow made a difference.

But that doesn’t mean that the experience didn’t change us. Having once spent every waking moment together, Alex, Morten, and I don’t see each other that often anymore. While Alex and Morten still have critical roles at the company, sometimes weeks can go by and we don’t speak. When we do, it’s kind of like when old soldier buddies meet. You’ve saved each other’s asses, but you also know that you will never want to go through that stuff with them again. Ever.

So maybe it’s violating some cardinal rule to work with friends, but I don’t know of any other way.