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A founder I was meeting for the first time was telling me about her startup. She spent the first 15-ish minutes of our meeting describing her project. Then, once she’d told me everything she wanted to explain, she asked a question that, to her, seemed simple. She asked: “Why is nobody buying my product?”

It wasn’t the first time I’d been asked that same question by a founder. In fact, I get asked that question almost weekly. But something was particularly jarring about the way this founder asked. She did it in the same way she might ask me to…

Every entrepreneur faces challenging choices, but making the decision doesn’t have to be hard

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A few years ago, I remember meeting with an entrepreneur struggling with a difficult decision.

“We got an offer to buy our company,” the entrepreneur said as he sat down across from me and explained why he’d wanted to meet.

“That’s great!” I said. “Congratulations.”

“Thanks,” he replied. “But the thing is, we’re not sure whether we want to take it. It’s not a bad offer considering where we are. It’s just that we’re worried we’d be selling too early and be giving up a lot of potential growth by exiting now.”

“That could be true,” I agreed, remembering that…

It’ll completely change the way you raise venture capital

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I need to confess something: This article isn’t about fundraising. Yes, I’ve intentionally tricked you with a clickbait title. However, before you click away in anger, give me one additional paragraph to explain my deception, and then you can decide whether or not to keep reading.

As I write these words, I’ve published well over 150 articles about entrepreneurship here on Medium. During that time, I’ve noticed a concerning pattern. The articles I write about fundraising are always — ALWAYS — more popular than the articles I write about customer acquisition. But the most successful startups aren’t successful because they’re…

If you don’t have a good answer, you don’t have a good company

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Imagine you’re a venture capitalist in 1950 and I’m pitching you my startup. The concept for my startup is simple:

Push a few buttons on a portable, pocket-sized device, and someone will pick you up in their car and take you wherever you want to go.

The idea I’ve just described is the basic premise of Uber. Even back in 1950, Uber would have been a great idea. However, if you were trying to build Uber in 1950, you’d run into a significant hurdle: the technology to create Uber didn’t exist. No cell phones. No GPS.

While you surely already…

Could someone be telling you your billion dollar idea is stupid?

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When people discover I teach entrepreneurship for a living, they immediately assume I have a magical power to judge whether or not an idea is “good.” As a result, I often find myself in conversations — with founders, students, friends, family, the random plumber at my house fixing my toilet — that begin like this:

“I’ve got an idea for a business I want to run by you. Can you tell me what you think?”

If you have a decent bit of experience in startups, you’ve surely been asked the same thing. And, if you’re an entrepreneur reading this, you’ve…

Would you put a 5,000-year-old wheel on your Tesla?

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I was judging a startup pitch competition alongside a prominent venture capitalist. For the sake of discretion, I’ll leave him nameless here.

A founder was pitching us his web metrics tool. I thought it was a creative and unique approach to the problem, and I told him as much in my feedback. After my comments, the VC shared his thoughts. In a rather uncharacteristic move for VCs, he didn’t hold back his criticism. “It was a good pitch,” he said, “but I’m not sold. What you’re talking about here is a solved problem. The world already has Google Analytics. It’s…

Changing the world doesn’t always go according to plan

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For most people, social media is part of the fabric of modern-day life. Heck, you’re probably reading this article because of social media. But do you know where digital social media started?

It wasn’t Facebook. Facebook launched in 2004, which was decades after computer networking began. MySpace, its well-known predecessor, only launched a few months earlier in 2003.

Some people might point to Friendster, which began in 2002. And, before that, back in 1997, there was a website called Six Degrees. Its creator actually filed the first patents for social networking. …

Not every business needs to become a career

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I was recently approached by an entrepreneur generating ~$30k per year with what she described as a “side hustle.” She wanted my help figuring out whether or not it was the kind of work she could turn into a full time career.

Her question got me thinking about the concept of side hustles in general. The term itself is relatively recent. It’s also — as far as I’m concerned — one of the best terms to emerge in the world of entrepreneurship.

I’m not sure where the phrase “side hustle” comes from or who first used it, but it’s a…

Startup success takes more than just having great ideas

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Kevin O’Connor sold his company, DoubleClick, for $1.4 billion. By any reasonable measure of startup success — and plenty of unreasonable ones, too — that’s a great outcome. But, if you talk to Kevin about it, you’ll learn something interesting. Even though DoubleClick was a success, he’d tell you it wasn’t his best startup idea. In fact, his best startup idea failed.

How can that be? Aren’t successful startups always based around great ideas? Lots of people assume that’s the case, but experienced entrepreneurs and investors know better. In truth, in the world of startups, the concept of a “great…

Interpreting investor interest isn’t alway easy, and there’s a good reason why

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“I just had a great meeting with a VC,” a founder was telling me. “He said he’s meeting with his partners later this week and would discuss our company. What are the next steps for fundraising? Do they give us their term sheet? Or do we need to get with a lawyer to create a term sheet and then send it?”

“Hmm,” I said. “Maybe I missed something. Why do you think a term sheet is coming?”

“He said he really liked what we’re doing,” the founder responded. “When he asked if we had any other investors, we told him…

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 @

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