How Curiosity Kills Entrepreneurs

Aaron Dinin, PhD
Aug 20, 2020 · 7 min read
Photo by Catherine Heath on Unsplash

At the university where I teach entrepreneurship, the start of the semester (which, as I write this, is right now), always brings a handful of emails that remind me of one of the biggest traps entrepreneurs fall into. The emails go something like this:

Dear Dr. Dinin,

I’m really interested in taking your class, but I’ve already reached the limit for the maximum number of credits I can earn this semester. Can I still take your class even if I’m not enrolled?


Enthusiastic Student

I realize, at first glance, that kind of email doesn’t seem particularly problematic. It might even seem good. After all, what’s bad about students who are so interested in classes that they want to “learn for the sake of learning” regardless of whether they earn any credit? Aren’t those exactly the kinds of students schools want? More importantly, for the argument of this particular article, isn’t natural curiosity and an eagerness to learn exactly what we’d expect to find in a successful entrepreneur?

The answers to those questions are more complex than they might seem. Yes, entrepreneurs should be excited about learning for the sake of learning as opposed to earning any sort of direct credit or reward. But that same enthusiasm can derail potentially great entrepreneurs (and students!) before they ever have a chance to become great. I know this, because, as I look back at my career, I know it happened to me.

The biggest limitation to learning

Personally, I love learning. I’m curious about arts, sciences, and humanities. I’ve studied topics ranging from healthcare to business to law to politics. I’m not suggesting I’m an expert on all of those things. Far from it. I’m just noting that I’m usually as eager to read a book by Stephen Hawking as I am to read a book by Jane Austen.

That natural curiosity created huge problems for me in my 20s because I was building tech startups while going to graduate school for English.

I don’t mean to suggest that entrepreneurs can’t be interested in literature. Nor am I suggesting that English majors can’t be entrepreneurs. In fact, in my experience, many of the best entrepreneurs I’ve met have humanities backgrounds (history, philosophy, literature, etc.).

However, no matter what we’re interested in, all of us only have the same 24 hours in a day. In my case, trying to build startups while being a graduate student never worked well because I didn’t have enough time to devote to either. All three companies I started while in grad school ultimately failed because there weren’t enough hours in a day to get customers while also reading 800 page George Eliot novels. I had to make tradeoffs, and the tradeoffs I made to finish my degrees cost me investors, customers, and employees.

In retrospect, my problem was that I couldn’t moderate my natural entrepreneurial curiosity and passion for learning. That inability to control myself ultimately cost me my companies.

The two personality traits all entrepreneurs have

Entrepreneurs come in all different shapes and sizes. They come from different cultures and different backgrounds. They have different beliefs, passions, and motivations. But, in my experience, all entrepreneurs share two common personality traits. The first of those traits is that they’re naturally curious.

I hope nobody is surprised by my assertion that entrepreneurs are curious people. After all, entrepreneurs have to be curious. They have to want to understand the world around them because understanding the world is what allows them to discover new market opportunities.

Put another way, if you’re not naturally curious about the world around you, you might see plenty of problems with it, but you’re not going to want to understand why those problems exist. Instead, you’re going to accept the world for what it is. Sure, you might complain from time to time when things don’t work as well as you want them to, but that’s the extent of your interactions with the world’s problems. You’re happy to complain about them but not curious enough to want to understand why they’re broken. In contrast, entrepreneurs love understanding why something is broken.

But entrepreneurs aren’t the only people in this world who are curious, so curiosity, alone, doesn’t make someone an entrepreneur. Instead, their curiosity allows them to understand why things are broken, and, once they understand why something is broken, they want to fix it. That, in turn, leads to the second trait that’s common to all entrepreneurs: they enjoy learning.

Learning is the entrepreneurial compliment to curiosity. In one respect, being curious teaches you new things, so you’re learning simply through the act of curiosity. In addition, as an entrepreneur, you also have to learn new skills in order to fix whatever is broken. Maybe that means learning about a market or learning about customers. Or it could mean learning new skills like fundraising, sales, coding, or management. Whatever the case, learning is such an important aspect of entrepreneurship that you’d better enjoy it, otherwise you’re not going to get very far in your entrepreneurial journey. Heck, you probably wouldn’t even be reading this article.

The dangers of curiosity and learning

While being curious and loving to learn new things are necessary qualities for successful entrepreneurs, those same traits present an enormous obstacle. Curious entrepreneurs quickly discover that the world is full of new things to learn. And because of this, entrepreneurs get easily distracted.

I see this happen all the time. Entrepreneurs I’m working with are maniacally focused on their ventures until, through their natural curiosity, they recognize something else that’s broken and start to ask themselves why. So they start learning more about it. And, as they learn more about it, they start wanting to learn how to fix it. Soon, the entrepreneurs who were so focused on one venture are trying to juggle two ventures. Two ventures turn into three. And three can turn into four. And so on.

But those ultra-curious entrepreneurs are still constrained by the same 24 hours in a day as everyone else, and each new project requires more time. As the entrepreneurs become overextended, they can’t devote enough time to any one project, and, as a result, all their projects suffer.

A third trait all great entrepreneurs need

It’s easy to tell when young entrepreneurs are starting to overextend themselves because they do something very similar to what over-enthusiastic students do when they email me to ask if they can take a class even if it’s not for credit. When entrepreneurs I’m advising — either during a conversation or via an email — begin asking for advice about industries or projects unrelated to the ventures they’d previously been working on, I know they’re struggling to manage their natural curiosity.

To be clear, their questions aren’t always overtly about starting new ventures. In fact, they’re usually much more subtle. One day, an entrepreneur I’m advising might ask, “Hey… what do you think about bitcoin? Is that worth investing in?” Or they might mention joining the board of a local nonprofit. Or maybe they bought a 3D printer to tinker with and can’t stop talking about how much potential they think the 3D printing industry has.

At that point, I know what’s happening. The natural curiosity of entrepreneurs is starting to pull them away from their ventures.

When I see something like that happening, I don’t try to stop the entrepreneur. After all, maybe that particular entrepreneur is better off focusing on something else if a current venture can’t keep the person’s attention. But I’ll usually talk to the person aout a third trait that not all entrepreneurs have, but all great entrepreneurs need: focus.

Being curious and loving to learn new things are great qualities for entrepreneurs, but the successful ones also know how to focus. I point this out to entrepreneurs by sharing the exact same story about students trying to get into my classes that I’ve shared with all of you, and then I explain how I always respond.

The importance of finding entrepreneurial focus

When students ask to join my classes even if they can’t get credit, I always turn them down. It’s not because I’m mean or I don’t want to teach them. It’s because I’m trying to protect them from making the same mistakes as me.

Here’s the basic gist of my response:

Dear Enthusiastic Student.

That’s great! I’m glad to know you’re interested in my class. Unfortunately, it would be irresponsible of me to let you join. In my experience, despite their best intentions, students who take too many classes inevitably aren’t able to devote as much time as they’ll need in order to be successful. Their struggles negatively impact themselves as well as their peers and professors.

I look forward to welcoming you into the class in a future semester when it better aligns with your schedule.


Dr. Dinin

Obviously, my specific response varies from student to student and usually isn’t quite so “cold,” but hopefully you get the general point I try to convey. No matter how great a student’s intentions, when they overcommit, they aren’t going to be able to devote the necessary time and resources to succeeding. As a result, they’re going to struggle in everything.

In the classroom setting, I’m in a position to stop students from overcommitting because I can simply not let them join the class. But, for entrepreneurs, the only people that can stop them are themselves. All someone like me can do is tell the story I’ve told here, talk about my own mistakes with trying to juggle too many projects and commitments at the same time, and explain how my inability to focus caused my companies to fail.

After I tell entrepreneurs these stories, I remind them that they don’t have anything to protect them against themselves and their natural entrepreneurial curiosity. All they’ve got is their own discipline. Can they find the focus to succeed? Or will their curiosity ultimately kill their startup dreams?

The Startup

Get smarter at building your thing. Join The Startup’s +789K followers.

By The Startup

Get smarter at building your thing. Subscribe to receive The Startup's top 10 most read stories — delivered straight into your inbox, once a week. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Aaron Dinin, PhD

Written by

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +789K followers.

Aaron Dinin, PhD

Written by

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +789K followers.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store