Here’s the Real Reason Entrepreneurs Struggle with Fundraising

I couldn’t raise venture capital for 3 years because I kept making the same mistake

Aaron Dinin, PhD
The Startup
Published in
6 min readFeb 11, 2021

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Since you’ve clicked on an article that’s clearly intended to give advice about pitching investors, I’ll wager this isn’t the first time you’ve read an article containing fundraising advice. That’s great! If you’re an entrepreneur thinking about taking investment, you should be researching the fundraising process. You’d be a fool not to.

However, most fundraising articles — including many of my most popular articles — tend to have the same flaw. They often treat “investors” as a monolithic group with the same expectations, ambitions, and strategies. As a result, those same fundraising advice articles usually present their advice as though it’s applicable to all fundraising scenarios.

Not only is that not true, it can be harmful, especially for first time founders who don’t have experience with the fundraising process.

The reason I know this to be true is because it’s exactly what happened to me. As a young founder trying to raise my first round of capital, I researched as much as I could about fundraising. Unfortunately, all the advice that seemed so helpful at the time was actually guaranteeing my fundraising efforts would…

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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