How Do You Really Feel As A Startup CEO?

I’d love to sit here telling you that being a CEO was great, and it was great. Truly, truly great. However, I’d be lying if I told you there was only one feeling I had being CEO.

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Picture: Depositphotos

There were times I felt immense pride:

There are two moments that stand out to me:

A. The moment we got funded.

I was in the kitchen of my house on the phone with Marcia, our lawyer. The first chunk of funding from one of our investors was deposited into our account.

B. The moment I knew we had arrived.

I remember that moment like it just happened. I was just finishing a meeting in our large conference room. I walked out of the room with my guest, and I heard this low roar of people talking.

There are the moments when you feel incredibly blessed.

This may not sound like a moment when you feel blessed, so bear with me on this one. Here goes.

And there were times when I felt like crap.

There are almost too many times to count when I felt horrible as CEO. However, there are a couple though that truly stand out.

A. The time a potential investor told me I was the reason they weren’t going to fund our company.

Near the end of our initial fundraising process, we were engaged with a very well known Sand Hill Road fund. We had gone through a cycle of meetings, and all that was left was a final presentation to the whole partnership.

B. The time Raul told me his fund would not support our next round of funding.

The move made no sense at the time. We were doing well. Revenue was up, and we were releasing a string of successful products. Plus we had just received a term sheet that Raul had already agreed to.

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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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