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

brett fox
5 min readFeb 8, 2021

“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.

Picture: Depositphotos

However, the reality was I really did just want to breathe. We’d raised our Series A over two years earlier, and, at that point in time, I’d been running the company for over four years.

I kept asking myself, “Would it ever get any easier?”

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 :-)).

Winston said to me, “You’ve done everything you said you’d do.”

I smiled and said, “Thank you.”

“We’re definitely interested in moving forward,” he said. He stood up, and I shook his hand and Irwin’s hand.

As I walked back to my car, I thought about everything I had been through to get to this point. The list was really long, but I’ll…

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brett fox
brett fox

Written by brett fox

I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at https://www.brettjfox.com

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