What Are The Pros And Cons Of Working With Your Friends?

Successful businessman being thowing up by his teamwork or colleague. Feeling and emotion concept in success and team work.

One of my closest friends was a cofounder of my company. Another friend was a cofounder of the company too.

And he recommended we bring on another friend as a founder. The only person who wasn’t a friend before we started was our VP Engineering.


You have to be prepared to lose your friendship if you go into business with a friend.

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“Ken” and I had know each other for over 20 years when we started the company together. We had vacationed together. Our wives were friends too.

In fact, I don’t even know if I would have, or could have, started the company without Ken’s help and support. Ken was critical to our getting our first investor.


That being said, I haven’t spoken to Ken since the day he quit with no notice.


Ken had to go. His performance wasn’t up to what it needed to be. I had been pushing him to improve for months.

I got to the point where I was willing to push him one more time, knowing that he might quit. So I pushed and Ken quit with no notice.


I don’t regret hiring my friend even though he failed.


Ken was the best sales executive I have ever worked with. He was, in his prime, a sales machine.

Ken knew how to manage and build a solid team. We agreed on the same sales methodology. There wasn’t even a question that Ken was the right person, and the best person, to run sales.

It was a coup to have Ken as part of our team.

That’s what made his downfall such a bummer.

I envisioned us working together for years building the company. We would have a great time, and we would get to live out our dream.

But it was not to be.


You’re the CEO. And that means you’re going to have to do some really unpleasant things.


Pushing on Ken to improve which resulted in him quitting was one of the saddest moments of my time as CEO. But I had to do it.

The company deserved a great VP of Sales, and Ken wasn’t capable anymore of being that person. So he had to go. I’m still sad about it to this day.

For more, read: How Do You Fire Your Cofounder?


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