5 Mistakes New Entrepreneurs Make When Cold Emailing Prospective Investors, Mentors, and Customers

Aaron Dinin, PhD
7 min readJan 14, 2020

In the startup world, it’s hard to overstate the importance of networking. The old saying about how “It’s not what you know, but who you know” is frustratingly true, particularly for new entrepreneurs. The problem, of course, is that new entrepreneurs don’t yet know enough people. How could they? They’re just getting started.

Once they realize the importance of networking, the savvy ones start searching for members of the startup community who seem worth talking to and sending unsolicited emails. In the startup community, we call these “cold emails” because it sounds better than “SPAM.”

I have no problem whatsoever with either sending or receiving cold emails. I’ve personally sent hundreds of cold emails to other members of the startup community, and I’ve received nearly as many. I believe it’s a critical part of the entrepreneurial landscape that needs to be nurtured and encouraged.

In that spirit, now that I’ve reached a point in my career where I’m receiving more cold emails than I’m sending, I want to point out the most common mistakes.

Fundamentally, all of the mistakes I’m going to discuss are a result of the same problem: not considering the perspective of the recipient.

From the perspective of cold email recipients, unsolicited emails create new work they didn’t have before you emailed. It takes work to read your email; it takes work to think about how to respond to your email; it takes work to actually respond to your email; and it takes work to execute any activities agreed upon in the email (e.g. a call, a meeting, an intro, or whatever).

Because your cold email is going to create work, and, presumably, you’re emailing people who already consider themselves busy, your goal should be to create as little additional work as possible from the initial email in order to generate a response that moves the relationship forward.

Let me repeat that, bold it, and italicize it because it’s critical: the goal of your cold emails should be to create as little additional work as possible while generating a response that moves the relationship forward.

Aaron Dinin, PhD

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