What Will Surprise You Most About Being CEO?


“Are you having fun?” Bob, our one and only angel investor asked me after we got funded.

“I’m having the time of my life,” I told Bob.

And it was true. I was having the time of my life.

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I had been preparing for this moment for most of my professional career. Every position I had built upon the previous position.

So, by the time I became a CEO for the first time, I had about 20 years of preparatory experience. I had worked with great role models like the late Jack Gifford, Maxim’s CEO, and the late Ziya Boyacigiller (also of Maxim).

I learned a ton about being a CEO working with Jack and Ziya. Jack and Ziya taught me how run a company, build an organization, discipline, and so much more.

I also learned a ton about not being CEO from some of the other CEOs I worked with like “Bob”. Bob was the classic Emperor that wore no clothes.

Bob never wanted to know the problems his company had. Eventually not wanting to see reality would cost Bob his company.


In fact, I learned so much about being a CEO that by the time I became a CEO that nothing about the mechanics of being a CEO surprised me.


However, there was one thing that none of the years of working with my mentors (good and bad) could have prepared me for.


I was not prepared for the loneliness of being CEO.


The decision making part was easy. The what do next part was easy. Even the really tough decisions were easy to make. But I quickly realized that you really can’t share your concerns with anyone inside the company.

You have to be so careful what you say to someone, even your fellow cofounders, because that information has a funny way of being distorted and passed to everyone in the company. And then you end up in an endless cycle of damage control.

You can’t go home and share your frustrations with your spouse either. I learned that really fast too.

You’re living with whatever crisis or problem you have all day. And then you unload everything on your spouse. That’s a recipe for divorce.

Okay, well your board will surely want to help you. After all, they have a vested interest in your success.

And it’s true that your board does have a vested interest in your success. However, you can also scare your board if share too much of your concerns with them. That can cause your board to lose faith in you if you’re not careful.


That’s why being a CEO is a lonely job; there is no one you can freely share your concerns with.


I did find two people that did help relieve some of the loneliness of being CEO. The first was my best friend Steve.

Steve and I had known each other since grade school. And even though Steve was in the broadcasting business, just being able to talk to him openly helped.

The other person that helped a lot was my friend and mentor Dave. Dave had been a VC, and Dave had been a CEO, so Dave helped me navigate both worlds.

Dave and I used to speak once a month for about an hour or so. Sometimes all that came from a call was one useful nugget that I could use. Other times, it was just his reassurance that I was on the right path.


Look for someone who only has an interest in your success to share your concerns with.


Find someone like Steve or Dave. Friends or mentors that only care about your success are the best cure for the loneliness of being CEO.

For more, read: What is it Really Like to be a Startup CEO?


Do You Want To Grow Your Business?  Maybe I Can Help.  Click Here.


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