The Characteristics of Entrepreneurship

James, Founder of Grindology and Startup Story

There is this false idea that entrepreneurship mirrors that of the movie classic, Field of Dreams. The idea that “if you build it, they will come.” If you develop the app or launch your e-commerce site, customers will immediately discover you, and all the expected riches will follow. The problem with that false idea is that it neglects any understanding of the characteristics of entrepreneurship.

Your newly developed product or service does not guarantee success, and to be honest, neither does “grit” or “resilience.” Sure those play a role, but entrepreneurship is a bit more complicated than most media headlines. I know this truth more than most because I have a graveyard full of failed startups in my past. Yet, it was those failures that helped me to understand the characteristics of entrepreneurship truly.

My name is James McKinney, and I am the Creator and Host of The Startup Story podcast and the new entrepreneurial subscription brand, Grindology. My entrepreneurial journey to creating The Startup Story, and subsequently Grindolgy, is one that, in my opinion, exemplifies the characteristics of entrepreneurship. While I won’t go into great detail into my entire entrepreneurial journey, you can hear all of it in Episode 50 of The Startup Story.

 James Startup Story

What I would like to share with you in this piece is what I believe are the characteristics of entrepreneurship that will exponentially increase your chances for startup success. I want to make sure you note that I did not say “guarantee your chances for startup success. There is no guaranty when it comes to entrepreneurship.

Characteristic #1: Humility

Right away, many of you began scanning the rest of the article to determine if the other characteristics warranted your time to read the rest. That’s OK because the characteristics of entrepreneurship that I will share with you come from the thousands of hours I have spent sitting with enormously successful founders. These aren’t merely my thoughts; they are truths synthesized from hundreds of different founders who exemplify these characteristics. 

After my fourth failed startup, I had a tough time processing why everything I ever started ended up in failure. I could not wrap my head around why others were succeeding, and I wasn’t. To find out what others were doing right, I started reaching out to some incredibly successful founders to understand their story and how they were able to reach the heights that I was desiring. Across the board, every single founder shared a story about a critical moment when their startup might not have succeeded if it weren’t for the guidance, advice, or learning they received from someone farther along the journey than they were.


Let me be clear though, it was the risk of failure that forced them into a position of humility to seek the guidance and advice of someone else. These successful founders had realized they needed the insight of someone more knowledgeable and more experienced than they were. As founder after founder kept reiterating some variation of that narrative to me, I realized I had not followed that script when it came to my entrepreneurial journey.

See, I bought into the idea that, as the founder, I had to be the expert of my own business. I had to know everything about it, and therefore I handicapped myself from seeking out guidance and wisdom from those who were farther down the road than I was. The ego will handicap many people, and entrepreneurs are no different. Do I ever reflect on my past ventures and wonder, “what would have been if I only…”? I try not to, but there are moments that I do pause to reflect on how fortunate I am to have access to so many great minds.

Does “humility” have the bravado of a characteristic like grit or resilience? No, but the characteristics of entrepreneurship are not about bravado; they are about increasing our chances for success, and it starts with humility.

Characteristic #2: Fearlessness

How many “ideas” have you had in your life that you saw someone else bring to market years later? I can personally think of three ideas that I had in the 1990s and early 2000s that have since become developed solutions or viable businesses. What stopped me from moving when I came up with the idea? Uncertainty and inadequate understanding of the market.

step by step - startup

Who am I kidding?! I was afraid of failing. Fear not only stops us from starting something, but it also causes us to get “stuck.” That “stuck” is fear of getting the next step wrong, or [insert any other fear you may have]. 

In 2009, I lost everything. In the span of 30-days, my business had gone from holding a contract worth close to $750,000 to holding a cancellation notice that led to bankruptcy. Even more humiliating was having to tell my wife how my missteps caused us to lose the very house she made a home for my young kids and me. As I said earlier, I am not going to go into detail in this article, so make sure to listen to my full episode of The Startup Story if you want to hear how it all happened. 

I give you that snapshot though because I understand fear and how paralyzing it can be, especially when your history reminds you of how you have yet to succeed. What is fascinating is that even the founders I have met with that have proven success still have a measure of fear they need to work through.

The characteristics of entrepreneurship include fearlessness because the fear of failure is inevitable, yet we need to keep moving forward despite that fear. Entrepreneurship is already incredibly difficult, and when you add the fear of failure to the mix, it becomes exponentially more challenging. 

Fear of failure is part of the journey. Do not try and avoid it; try to stop it from paralyzing you. 

don't give up

Characteristic #3: Strategic Listening

Look, you’re a bit crazy for wanting to start your own business. That is just the hard truth, and most people around you are not as crazy. For that reason, those closest to us are going to think that what we are pursuing is “irresponsible,” “foolish,” “wishful thinking,” and/or a “waste of time.” Have you heard any of those before? 

I’m OK with others having that perspective because I understand that most people are wired differently than I am. What I am not OK with is allowing their opinion and perspective to be the only voice in my head. For that reason, we must surround ourselves with people who are just as ambitious as we are. Attend meetups, go to pitch contests, work out of a coworking space; you have to be intentional about surrounding yourself with like-minded people. Again, you cannot shut out those closest to you, but you can definitely water-down the impact of their skepticism.

listen to advice

Now, if you are still reading, then it is probably safe to assume that you are serious about understanding the characteristics of entrepreneurship, so I’m going to help you out by drawing your attention to a potential trap.

These three characteristics will fight for your attention, and the most comfortable one will usually win.

  • When being intentional about who we listen to, it is easy to isolate ourselves and therefore neglect the characteristic of humility.
  • In our attempt to not allow fear to paralyze us, we might fail to share our ideas with others as to not appear timid in our approach.
  • As we surround ourselves with equally driven people, we have the propensity to “drink our own Kool-Aid” and neglect advice from others ahead of us.


Exercising the characteristics of entrepreneurship is an intricate dance. That said, there is a reason Humility was number one. If you lean in on humility, the chances are much greater for the other two. As you seek guidance and mentorship from those further along than you, they will give you the courage needed to make some tough decisions because they have been there. Those same people will also speak the truth you need to hear that will help drown-out the nay-sayers in your life or validate what those nay-sayers are saying.

If it seems counterintuitive to pursue entrepreneurship from a posture of humility, that is because you’ve listened to the media headlines for guidance. I suggest you start listening to those who are trying to build a business. Entrepreneurs like you and me.