Working With Your Friends Is Okay…But Firing Them May Be Part Of The Deal

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

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Picture: Depositphotos

And he recommended we bring on another friend of his 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.

“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 our Sales VP, and Ken was critical to our getting our first investor. At the time Ken was living in London running European sales for another company, and he was planning on moving back to California in the next month to join us.

Gill, our first investor, was adamant we have someone with heavy sales experience in the company. I set up a call between Ken and Gill. Gill was impressed with Ken, so he moved forward with the investment.

Working with Ken started out great until he had to start traveling.

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.

For whatever reason I started getting the feeling that Ken thought that running sales was going to be easy. The first clue there was going to be a problem was when Ken decided to live in a very high end condominium in San Francisco. That meant Ken was going to have to drive over an hour to get to our headquarters in Milpitas.

I shrugged it off at the time. After all, Ken was going to be on the road most of time, so it didn’t matter where he lived.

Another mutual friend of ours told me a few months later that Ken was the “mayor” of the complex. “Everyone knows Ken,” he said. I began wondering some more how Ken could be the mayor and be staying at Holiday Inns at the same time?

We announced our first product about nine months after we closed our funding. Before the launch Ken mapped out his travel schedule.

Ken was planning to be on the road about 80% of the time. It made me feel bettter.

Then we announced our first product and Ken was scheduled to be traveling the whole week visiting with customers. Ken was back in the office on Wednesday.

I was traveling that week visiting customers too. When I got back in the office on Monday, we had our weekly 1:1.

You’re likely to lose your friendship if you fire your friend.

I asked Ken what happened. Ken told me his visits for the rest of the week were canceled.

The Ken I worked with years ago would have never allowed that to happen. The Ken I worked with years ago would have had backup visits set up.

I grit my teeth, and I asked Ken about his visits for the next week. Ken told me they were all set up.

Then Ken was back in the office again on Thursday. This time I took Ken out to lunch, so we could talk.

My sense was that Ken was just burned out. So I decided at lunch to ask Ken directly.

Ken told me, “No, I’m not burned out.” Then I said, “You know you’re going to have make each trip count. That means five days, not two days.”

Ken nodded his head in agreement.

The next morning Ken emailed me at 9:00AM. The title of the email was “Resignation.”

Ken was resigning with no notice. I didn’t try and change Ken’s mind.

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.

You can’t let a friendship you have get in the way of doing what’s right for your company. You have an obligation to your team, your investors, and your customers that is bigger than any friendship you have.

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

I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at

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