The Five Most Likely Problems You’ll Face As A Startup CEO

“I just want to be able to breathe,” I said to Irwin and Winston, two VCs I was meeting with as I began raising our Series B funding. The second I uttered those words, I wanted them back. I thought my words exposed my inner feelings, but Irwin and Winston just moved on with the conversation.

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Picture: Depositphotos

Every stage of your startup journey is going to have its share of challenges.

I stayed focused during the rest of the meeting, and Irwin and Winston seemed impressed. They’d been following my progress since I pitched them during our Series A (they passed :-)).

Problem Number One: You will likely be your toughest critic.

Actually, my first thought was, “I don’t feel like we’ve accomplished enough.”

Problem Number Two: You’ll likely have to adjust your sales and marketing plans.

One of the advantages we allegedly had, and one of the selling points we sold to potential investors, was the experience of the team. Each of the founders had over 20 years in industry.

Problem Number Three: Some of your co-founders won’t make it.

“’Randy’ and ‘Ken’ are no longer with the company,” I said to Irwin and Winston when I got to the team slide.

Problem Number Four: You’ll be at the bottom of the “J” Curve.

The J curve is the low point in the valuation of a startup. It usually happens in early stages of the company. Visually, it look like this:

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Problem Number Five: The investment climate may change.

Irwin and Winston went down the path to pursue an investment with us. But they weren’t moving as fast as I would like.

You need to learn how to take a punch.

You’re gonna get punched as a startup CEO. In fact, this theme became a mantra for me. So I wrote a book about it.

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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