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Photo by Gonzalo Arnaiz on Unsplash

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…


Hint: investors are never impressed by entrepreneurs who are “crushing it”

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Photo by Austin Distel on Unsplash

When I was first learning to fundraise, I believed I needed to convince investors of two things: 1) that my startup was awesome; and, 2) that I was an exceptional entrepreneur. In my mind, the best way to accomplish those two things was by learning how to give a perfect fundraising pitch.

I read countless articles about how to pitch investors. I spent hours practicing my pitches in front of trusted mentors. I even recorded myself giving my pitch, then I would dissect the videos like a golfer who records his swing then analyzes it for flaws.

Thanks to all…


The man who invented fact-checking shows how founder stories can’t always be trusted

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Photo courtesy Connor Danylenko via Pexels

So you want to be an entrepreneur, huh? You’ve watched a few movies about people like Steve Jobs and Mark Zuckerberg. You’ve been reading Techcrunch religiously for years. And you’ve carefully studied every fundraising article on Medium. The only thing left to do is keep brainstorming until you come up with your world-changing idea.

It’s a flawless plan. Well… almost flawless. It overlooks one important detail: that’s the “fake news” way of becoming an entrepreneur. Sure, I suppose it could be possible. You could be a “visionary” who — through sheer force of will — thinks up an incredible opportunity…


Facebook could do a better job explaining its value proposition

Two white doors side by side, each with a sign that says “FREE” and “PRIVATE
Two white doors side by side, each with a sign that says “FREE” and “PRIVATE
Photo illustration, sources: Mohamed Elkhamisy/EyeEm; Jose A. Bernat Bacete/Moment viaGetty

By now, most people already know Facebook and its CEO, Mark Zuckerberg, are hell-bent on capturing user data and making money off of it (the subject of at least two popular documentaries about it on Netflix). And now, in a bold demonstration of force, Apple CEO Tim Cook has come charging in atop his noble white steed (also available in Space Gray™ and Rose Gold™) to protect consumers. …


Taking on a market leader isn’t easy for entrepreneurs, but, with the right strategy, there’s a way to win

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Photo by Thao Le Hoang on Unsplash

From an entrepreneurial perspective, enormous markets have an obvious advantage: The more potential customers you have, the bigger your company could become. And, of course, we see this play out all the time. For example, everyone in the world wears shoes, meaning the shoe market is enormous. As a result, companies like Nike and Adidas are some of the largest in the world.

The corollary to this is that enormous markets have lots of competition. In the case of my shoe companies example, Wikipedia lists 388 different shoe companies worldwide. And that list is nowhere near exhaustive. …


Every entrepreneur has to learn to sell, and it’s a lot easier than you think.

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Image courtesy Andrea Piacquadio via Pexels

When I was a young entrepreneur first learning to build startups, an early mentor gave me a piece of advice about sales that seemed ridiculous at the time. Then I actually tried it and was amazed by how well it worked.

I still remember our conversation. We were sitting in a coffee shop in Philadelphia and I was complaining about a potential customer I’d spent hours trying to close. The prospect backed out of the deal at the last minute because it “wasn’t what they really needed.”

“No matter what I said, I couldn’t convince her to change her mind,”…


For many companies, unexpected circumstances became the perfect storm for massive growth

An animation of a man riding a “startup” rocketship with dollar signs upwards on a graph tracking Growth against Time.
An animation of a man riding a “startup” rocketship with dollar signs upwards on a graph tracking Growth against Time.
Animation by Carolyn Figel for Marker

“Coronavirus is the black swan of 2020.” So began the ominous letter that venture capital firm Sequoia Capital sent to the founders and CEOs of its portfolio companies on March 5 of last year. In many ways, the note was prescient, published roughly a week before the rest of white-collar America shuttered their doors and pivoted to remote work.

I remember receiving a similar pandemic-panicked email in my inbox around the same time as the Sequoia note. It essentially declared: “Nobody is allowed to come into the office until further notice.” I was in a meeting with approximately 20 other…


Entrepreneurs spend lots of time thinking about who they’re helping, but they also need to think about who they’re hurting

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Image courtesy Andrea Piacquadio via Pexels

When building startups, entrepreneurs focus almost exclusively on the needs of their target customers and how to best help them. And why wouldn’t they? After all, if, for example, you were building an app to help parents coordinate their children’s after-school schedules, why would you spend any time thinking about non-parents? Or if you were developing a device to help diabetics manage their condition, why would you spend any time thinking about non-diabetics?

In general, this kind of myopic focus on the people in your target market and their needs is necessary because it helps entrepreneurs make important business decisions…


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

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Photo by Petr Slováček on Unsplash

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. …


Despite all the headlines featuring names like Bezos, Gates, and Musk, fame isn’t an important part of entrepreneurial success

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Image courtesy Jon Tyson via Unsplash

Entrepreneurs are always chasing the newest technology trends because those are the things everyone is talking about. Whether it’s AI, machine learning, 3D printing, cryptocurrency, big data, social media, mobile, automation, IoT… if it’s a new technology that looks like it could dramatically impact the ways people live, you’ll find entrepreneurs trying to build businesses either using it or related to it.

This isn’t a new phenomenon. Back in the late 1700s, as mechanical automation was becoming a reality, entrepreneurs were trying to apply the same automation technologies to farming, textile production, transportation and everything in between.

To be clear…

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

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