Why Entrepreneurs Struggle Raising Their First Round of Venture Capital

Aaron Dinin, PhD
The Startup
Published in
7 min readJun 25, 2020

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Photo by Christian Erfurt on Unsplash

“That was one of the best presentations I’ve heard in a while,” the VC said. “You’ve clearly got something special here.”

“Thanks!” I responded. My first company was participating in a startup accelerator, and I was wrapping up a meeting with a VC I’d been connected to through the program. I’d never raised capital before, and, to that point, I’d been unsuccessfully fundraising for a while. But my skills were improving, and I felt like I was getting closer to success. I was hunting for my lead investor (back when I thought that was a real thing), knew I’d just nailed my pitch, and I was feeling increasingly confident this guy might be it. It was time for the big “ask.”

“So,” I continued, “We’re looking to raise about $1.5 million. How much would you want to invest and what kind of terms are you looking for?”

“Oh, I’m sorry,” he replied. “I’m going to have to pass. The company isn’t a good fit for me.”

“I don’t understand,” I said. “You literally just told me it was one of the best presentations you’d seen and that we’re clearly working on something special. What more could you possibly want from an investment? Isn’t your goal to find great founders working on great companies?”

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Aaron Dinin, PhD
The Startup

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @ aarondinin.com