I Sacrificed a $50 Million Company to Chase a Billion Dollar Business, and It Didn’t End Well

Not every company is meant to be a unicorn, and that’s OK

Aaron Dinin, PhD
The Startup
Published in
5 min readMay 6, 2021

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Image courtesy Pexels

I was walking into my fourth meeting with a venture capital firm that was considering an investment in my company. Yes… the fourth meeting. I was still early in my startup career, and I was just beginning to learn that successful fundraising was nothing like how it was portrayed in Hollywood or TechCrunch. You don’t just meet with someone once and then they write you a check for millions of dollars. Instead, before a VC invests, you’re going to have lots of meetings.

Seriously… LOTS of meetings…

Every firm has its own process, of course. In the case of this particular firm, once one partner was interested in my deal, he scheduled me to meet with the other partners individually so they could all give their perspectives. Why I couldn’t pitch everyone together at the same time, I have no idea. Instead, I was back at their office for the fourth time in two weeks to give another pitch. This time, I was pitching the senior partner.

I gave my pitch, he asked good questions, I replied with what I thought were good answers, and we talked for the better part of an hour. At the end of the meeting, the senior partner leaned back…

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The Startup
The Startup

Published in The Startup

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Aaron Dinin, PhD
Aaron Dinin, PhD

Written by 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