Should I Work With My Best Friend As A Cofounder?

I had a very close friend who was a co-founder of my company.  Here's what happened:

“You have an EQ of zero!” Ken yelled at me.

“What the hell is an EQ?” I asked.

“Perfect!” Ken screamed back. Then he hung up the phone. Those were the last words Ken ever said to me.

Just like that a twenty-year friendship and business relationship ended forever.

Ken was a co-founder of my company. More importantly I considered him a close friend.

I had lunch with Ken the day before to have our weekly 1:1. I pushed him pretty hard at lunch because he wasn’t performing well.

I looked down at Ken’s feet and he wasn’t wearing socks.

It triggered a memory of when we were raising money. We were in a diligence meeting with a VC and I vividly remembered the VC looking disapprovingly at Ken’s sockless feet.

I told Ken that day with the VC that he needed to wear socks.

At lunch I said nothing. But I was a little pissed off.

Over lunch, I went point-by-point with Ken about my concerns. Ken listened without saying a word.

I ended our lunch conversation saying, “Make life easier for us.”

Ken didn’t say a word as we drove back to the office.

The next morning at 9AM, I received an email from Ken. The title was “Resignation”:


I’ve decided to make your life easier by resigning. I will no longer come into the office, but I will make my last day May 30th, so I can vest one more month of stock.”

I immediately got on the phone and called Ken.

That’s when Ken yelled at me, “You have an EQ of zero!”

I haven't spoken to Ken since that day.  (For more on the story of what happened with Ken read:

You are correct in being concerned about what will happen to your friendship if your friend joins the company because the friendship may go away.

It seems, based on what you wrote, that your friend doesn't belong in your company. 

I would have a friend to friend talk and honestly tell your friend that he is not a fit.  I would add that you value his friendship too much to mislead him.

It may sting for a bit, but, if you deliver the message with true empathy, you likely will still have a close friend.

For more, read:

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