4 Traits of An Entrepreneur

Episode 28

In this episode, we'll be talking about 4 common traits of an entrepreneur referenced from this article Hiring An Entrepreneurial Leader.

  • Entrepreneurs are curious seekers of adventure, learning, and opportunity.
  • Entrepreneurs are more comfortable with risk.
  • Entrepreneurs are driven by a need to own products, projects, and initiatives.
  • Entrepreneurs are natural salespeople.

Find us on Twitter @The_Scott_Davis or @RobDickersonJr


Robert: In this episode of The Stretch Goals Podcast Scott and I are going to be talking about the four traits of an entrepreneurial leader.

Scott: This is The Stretch Goals Podcast, where each week we’ll share insights and lessons learned based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Scott Davis.

Robert: I’m Robert Dickerson.

Scott: I know what the four traits are.

Robert: You do? You already know?

Scott: Yup, yup.

Robert: Because you al-

Scott: Bald and sexy.

Robert: Because you already have-

Scott: Super nerdy.

Robert: You already have all the traits.

Scott: Exactly. Exactly.

Robert: I was reading this article in The Harvard Business Review and it was talking about hiring an entrepreneurial leader and I thought it was … It had some interesting bullet points in it that I thought would be interesting to talk about, both from our own experience as entrepreneurs. I found that they resonated … a lot of the traits resonated with me and my interest in it. I want to see your feedback, and also for the listeners to think about their own view of entrepreneurship and how some of these traits resonate with them, and also some ways that you can improve or learn them over time. I’ll link the article at ShowNotes so people can take a look, but let’s just jump in and go through there.

It was talking about the stereotypes, there’s these four stereotypes, and then really they outline the cellular truth that expanded on those stereotypes. The first stereotype was entrepreneurs are unusually creative, and then it outlined that the subtler truth was that they’re really curious, seekers of adventure, learning, and opportunity. Now, I feel like for me a lot of my career, a lot of my passion is learning new things, finding new opportunities I may have not seen before. I mean, what are your thoughts? Does that resonate with you that you’re looking for adventure?

Scott: I think … I don’t know that I’m looking for adventure. I’m definitely looking for learning and opportunity, but I think those three concept, adventure, learning, and opportunity are basically saying that you’re creative. I think that’s part of being a human being. I think everybody has that. I think entrepreneurs, if I’m reading between the lines here in this article, is that entrepreneurs are better at harnessing that adventurism, learning, and creative mechanisms in their body to then apply it to what they want. Whereas other people, sure they’re creative, but they maybe a little lazy or they don’t know how to network or something along those lines. I think entrepreneurs are greater at putting all of those pieces together to harness it for their own benefit.

Robert: I think that’s a really good point because we … When we were talking in episode 22 I said it about design, that was one thing that we were talking about, is that design can be learned over time. I do agree to that. I think everyone is creative, it’s just finding that outlet maybe and maybe having the time to pursue it. A lot of times that can be giving yourself the freedom and the time to pursue that creativity and let it come out. I know so often in jobs you’re given deadlines, you’re given … you have to have these things done at a certain time. There’s all these other mundane tasks you have to get done and so it’s hard to be creative. Now, I even find as an entrepreneur myself, there’s so many different things that I have to do. Sometimes it’s hard to just sit down and push all that stuff aside and really focus on the things that I need to be creative and avoid the distractions.

Scott: It’s like everything else, I think. If you’re passionate about a certain idea or you’re really interested in it, it lends the way to a better experience if you’re able to focus on it. You just have to find what’s interesting to you, and wherever it maybe and you go with it. I think to say entrepreneurs are unusually creative is true, but I think people are unusually creative, but what is true about what this is implying is that entrepreneurs are greater at putting all those pieces together and use it to their benefit.

Robert: How do you get better at doing that? I guess it just comes from practice, from trying different things. I think it’s something you can learn. Do you think that?

Scott: Yeah, we all learn it somehow. Obviously there’s a part of us that’s naturally inclined to do these types of things but … I remember when I got my first job at Food Lion at Mechanicsville, Rob, on 301. I put my application in, I was like 15 years old and I just put my application in and I’m like, “Oh, they’re going to call me back.” My mom was like, “No, you need to call them. You need to be assertive.” I learned my assertiveness from my mother. I remembered at that point, I’m like, “Oh, so when I apply for a job or I’m trying to like, reach out to somebody, it’s on me to make sure that that fulfills.” I remember that distinctly to this day. I think it is a learned thing. If I didn’t learn that I probably never really would have figured out the proper way because somebody showed me what to do.

Robert: I think being proactive, I mean I don’t know if that was a … that’s not really in our list, but I do agree that that is kind of identifying those opportunities and being proactive to go get them as opposed to waiting. I see so much in the job market that people think that a great cover letter or just sending someone an e-mail is going to be enough to get them a job. It’s so much more than that. It’s about going and getting the opportunity and proving … we’ve talked about this in other episodes as well, your credibility, it’s about proving that and seeking out those opportunities and seizing them.

Scott: Well, I think being proactive falls directly under seeking adventure and learning and opportunity. Being proactive applies across all of those in a sense.

Robert: We’ve also talked about as well that, for me personally, I enjoy finding new opportunities that are interesting and that could be the adventure side of things, is that you’re going down a path maybe other people haven’t travelled. As an engineer that’s solving problems and figuring out ideas for new problems is something that I really enjoy doing. I can see myself going down that path as well, where I’m trying to learn new things, I’m trying to identify opportunities. I’m trying to work with people that are really pushing the boundaries and trying to find new ways of doing things.

For example with Mapout, we’re really pushing the boundaries in digital health and healthcare, and trying to find opportunities around that. I’ve been aligning myself with people that are thinking about those areas that are working in those areas, and then I’m able to align myself with those people and move my own knowledge forward, my own learning forward based on the things that they’re doing.

Scott: Well, I think it ties in with the next stereotype mentioned in the article, which is entrepreneurs enjoy and seek risks. Then the more subtle truth about was entrepreneurs are more comfortable with risks. That’s part of the first [inaudible 00:07:02] which is seekers of adventure. I don’t know that I personally seek risks, but I look at risk differently than other people, and maybe it’s because I’m a software developer. I know that if I have a software idea I can just build it, there is no risk to me. It’s something I’m interested in, I’m going to go build it. It’s not like I am jumping off a building or something without a parachute. I’m doing something that I’m comfortable. To me, for what I’m doing, seeking risks isn’t really something I’m out for, but I do enjoy blazing new paths like, “All right, guess what, I just did this thing that very few people in this world have done from a technical perspective.” That really is something that I love to do.

Robert: I think risk too, it depends on how you define it. For me, when I see that, that entrepreneurs are more comfortable with risks, I see that they’re more comfortable with failure. They’re able to embrace maybe that failure-

Scott: Or they don’t take it the same way that everybody else does. It’s not like completely demoralizing and depressing.

Robert: How do you look at it when you look at failure? I mean, like for me I see opportunities.

Scott: I do.

Robert: It’s like you’re looking at that risks but you’re seeing the opportunities over the failures, I guess.

Scott: Look, I played baseball and you fail two out of three times when you step up to the plate. I’ve always taken it that way. It’s like there’s always an opportunity for improvement and it’s no different from sports or technology or anything. I think I’m just like you, it’s like every time you do something whether you succeed or not, you learn something during that process and you failed at something during that process too. You might have … Your goal was to get a 100 on your math paper, you got a 100 but you failed at something else in the process. You didn’t get a homework assignment done for some other class or something, but the point is you fail along the way to success.

If you just fail outright you learn more, because there’s more opportunity for you to grow, more opportunity for you to correct things. I actually enjoy that, like if you succeed it’s kind of boring. It’s kind of a buzz kill in a way and I don’t mean always, but I mean it’s like, “Wow, I did that and it went perfectly, now what?” But if you’re like, “Man, I did this thing and it almost worked the way I want,” now you’ve got the opportunity to make it work exactly the way you want.

Robert: Well, if you don’t go through the hard times the success isn’t as sweet, right? If you’re always succeeding, if you’re always doing things within your comfort zone then you’re never pushing yourself, you’re never growing. That’s kind of how I view it, is that by taking those risks you’re growing personally and professionally. I think for our listeners, look at the opportunities that you have out there, whether you’re starting your own business, whether you’re still working in a corporate world, try to identify those opportunities that maybe are outside your comfort zone. There’s people that are doing some cool things that are outside your comfort zone and give it a chance. Try to work on those opportunities. Try to develop new skills. Try to take your business maybe in a slightly different direction that maybe you think, maybe it’s a riskier path, maybe more prone to failure, but you could come out the other side and have all these different opportunities that you never would have if you hadn’t opened that door.

Scott: Well, what do you think about this line that says, “Entrepreneurs enjoy and seek risks,” like I don’t … How do you seek risks?

Robert: I don’t want to fail.

Scott: It’s interesting. It’s like, “I want to go out and be a gambler today.”

Robert: Well, yeah. Well, that’s why I like comfort because it’s more of a calculated, for me it’s more of a calculated risk. You’re weighing your options and maybe a lot of times it’s a gut feeling as well, that you weigh the pros and cons of a risk, and you just go down the path. So much about entrepreneurship is just a day to day gut feeling of making decisions, where you’re not really sure, you don’t have all the information. Even that in itself is a risk because you’re making these decisions, whether it’s design decisions, whether it’s sales decisions, whether it’s marketing decisions, whether it’s opportunities. Those are all choices and possibility risks, that if you go one way you’re closing the door somewhere else. You just have to be confident of your decisions and move on.

Scott: I think your confidence statement goes into the next stereotype which is, “Entrepreneurs are more personally ambitious than other leaders,” and then the more subtle truth about was, “Entrepreneurs are driven by a need to own products, projects, and initiatives.” I mean I do agree that ambition is a huge part of being an entrepreneur. You’ve got to blaze your own trail. You’ve got to have that drive and ambition is part of that. If you just sit there and do nothing you’re not going to be successful. I think that’s a very true statement, but it says, “Entrepreneurs are more personally ambitious than other leaders.” I don’t know about that, but I do think that having that ambition helps you to succeed as an entrepreneur.

Robert: It’s a trait that helps you as a leader, as an entrepreneur. I agree with what you said, is that I don’t know if they’re necessarily more, more ambitious than other leaders. Their ambitions might align better with the subtler truths, is that they have a need to own projects, they own products, and they own initiatives. For me, that really resonates with me throughout my own career, is that I’ve always enjoyed the ownership and I feel like to be a successful leader you need to give ownership and accountability to people to be successful. If you don’t give them that ownership then they’re not invested in what they’re doing. They’re not as motivated or invested to put their best foot forward, but by giving them ownership you’re saying that, “The success or failure of this rest on your shoulders.” Right, Scott? “You own this. It’s your project. It’s your initiative, own it. Succeed or fail.” Some people thrive in that. I really enjoy that, other people are not as comfortable, they might just want to go to the day to day grind and get out of the office.

Scott: I think that when you look at ambition as it pertains to a successful entrepreneur, it’s not so much about being ambitious as it’s looking at the barriers and how to break down those walls differently. We’ve all got this ability to be ambitious, but I think a … This ties back to the first point of the article which is creativity, with your ambition you use your creativity to figure out how to break down those barriers and allow your ambition to soar on its own. I think it’s not just ambition, it’s the ability to think of a path forward and reduce the barriers that are between you and your goal.

Robert: There’s not always a black and white to this or a right answer, right?

Scott: No.

Robert: There’s a lot of gray and I think that’s what scares a lot of people, is that there is so much gray that there is not … So much times in school we learn that there’s a right and wrong answer. There’s not a lot of gray there for people to make decisions. In life there is this huge gray area and in entrepreneurship there is as well, it’s where you take your products, how you act as a leader. I mean, there’s so many different ways to do it and there’s not a right or wrong answer. A lot of times you just have to learn on your own through experience, try everything, see what works. That ambition will help drive that, that you see a goal and you got to figure out how to get there.

Scott: This article reminds me of that book The Millionaire Mind, where they did a study on a million millionaires and found these common traits between them and were able to surmise all these different data because … I feel like one thing that stood out to me when I read that book years ago was, the average amount that a millionaire spends on an engagement ring was like $3,500, which if you look at the average at the time it was something like $7,500 for like the entire country. Basically what I’m saying is that or suggesting is that entrepreneurs are more careful about, not entrepreneurs, millionaires are more careful about how they spend their money.

This article is doing the same thing. It’s analyzing all these traits and then saying, “Here’s the things that are most common between all these people.” It wouldn’t surprise me if this article basically became a book because of all these startups and everything that’s going on in technology these days. Basically we’re going to see, if we hadn’t already, there maybe a book out there. Someone let me know in the comments, but there’s going to be this thing, “Here’s all the startups that have come up and here’s all the key traits between them.”

Robert: I think a lot of times there are probably key traits, but that doesn’t actually mean that if you don’t have those or you don’t have other traits that’s a bad thing. We just want to talk around these four traits because I thought they were interesting. Even if you don’t see yourself aligning with some of these things that doesn’t mean you can’t be an entrepreneur. That doesn’t mean you can’t start a business or you can’t be successful, it just means you’re going to do it differently and that’s a good thing. I think … Even some of these if you, maybe if you want to get better at it, maybe if you want to get better at being comfortable with risks, that’s something you can focus on or if you want to have ownership of products and things, to find a path to get there to do that.

Scott: Let me ask this question. This is a bit of a departure before we go on to the final item from this article, but do you think there’s such a thing as a risk-free startup idea?

Robert: No, I don’t think in life there is not. There is not anything that is risk-free because if you think about … For me, I always compared being an entrepreneur and working in a business, that the risks are very similar, but as entrepreneur you’re engaging with those risks and you are using your ambition, and your drive, and your motivation to, I guess, lessen the risks so to speak. Whereas when you’re in a company maybe some of that risks is taken away and other people bear the brunt of the risks, but it’s still a risky venture because you could just get fired or you could get laid off. You’re putting that in the hands of other people to manage, to manage whether or not you have a job, whereas being an entrepreneur and starting your own business you have control of that.

That’s why the third point of ownership really resonated with me, because even when I was in the corporate world I tried to get ownership of products and initiatives because I felt like if I had ownership I could control where it went, and success or failure rested on my shoulders and no one else’s. I enjoyed that, I enjoyed having that put on my shoulders. I think you have a similar trajectory as well in the corporate world, you engage in those projects too that put you in the ownership role. It puts you in the role where maybe you’re accepting more risks than other people in the company.

Scott: I thrive in those scenarios. I like to be in that position. I like to be the Tom Brady, if we go back a few episodes, but that’s it. I mean I like to be in control and working all those things that are interesting to me and like I said, “Blaze a new trail.”

Robert: I think control doesn’t mean that you are micromanaging. Let’s differentiate that a little just for a second. Control doesn’t mean that you’re micromanaging your team, that you’re micromanaging what gets done. It’s just you’re mapping out the vision of where you want things to go and you’re helping your team get to that path. You’re driving them down the path and for me that’s really the best part, is working with a great team, working with people and navigating and making decisions everyday to figure out how we’re going to get to the end and build something great.

Scott: What do you think about this last stereotype in this article?

Robert: The last one is that, “Entrepreneurs are natural sales people.” I don’t feel like I’m a natural sales person. Do you?

Scott: I’ve been told that I am.

Robert: Really?

Scott: Which is funny because I don’t … I don’t ever try to sell anybody on anything. I think what they mean when they say that is that they mean I’m naturally charismatic or I’m naturally … I don’t know. In clients, they connect with you-

Robert: Well, people … People want to work with you. People want to … You’re selling yourself more than products. We talked about the sales person role, I feel like sales people get a ne … When you say sales person it comes off as a negative connotation, you think about someone that’s hassling you and sending you e-mails all day, “Will you buy this?” Kind of the overbearing, over aggressive person, but that’s not really as an entrepreneur or what a sales person is. It’s connecting with people. It’s getting people to buy in to your vision, and your drive and your motivation, and people want to work with you. They want to … They see that you’re being successful and they want to work with you and have success of their own.

Scott: I think that’s what they mean by that. I don’t think they mean like, “Hey, you’re that sleazy, slick-back hair car salesman,” I think it just means that we’re just natural sales people. It means that we’ve got all the pieces we need to put our product in front of somebody in whatever way possible to gain attention for either personally or the product itself. I understand what it’s saying. I don’t by any means try to be a sales person. In fact I would hate my life if all I had to do was sell things to people, but in essence that’s what we do, Rob. I mean we haven’t been successful by not putting ourselves out there, I guess we are sales people. We’re a sales person of ourselves, our own brand.

Robert: I think that’s important. I like the idea of what you said a brand, and that’s something that early on in my career I didn’t really establish for myself, was a brand. That’s not something to say that, “I’m a great speaker or I’m a great entrepreneur,” or anything like that, but just establishing the things I’m interested in and speaking out about those things, and communicating with people as I view as a brand. Just to talk about the sales person, I’ve seen really good sales people, my brother is a really good sales person. He is really motivated. He thrives … I’ve talked to him about it, he thrives on identifying opportunities and going out there and meeting people. For him closing that deal, closing that sale is what really drives him and what motivates him.

For me, I don’t … I just don’t really, I guess maybe enjoy the thrill of the hunt so to speak, as much as I do just talking to people. Our style, while our styles are different I feel like we’re both sales people in a different way. For our listeners you can be that same way as well. You might not be someone that is a typical sales person that’s closing deals, that’s really aggressive, you might be laid back, you might be approaching sales in a different manner and that’s okay. It’s just finding your niche, finding the way that you are selling yourself, selling your products, selling your company and it can be different. It could be more laid back. It could be just establishing those relationships where people want to connect with you.

If we talk about sales people, how did you develop that trait to be a sales person? Was it just something that came over time? I know you said that you don’t really maybe think about yourself as a sales person, but was it just a passion for what you’re doing that showed?

Scott: I think it’s my personality that just would categorize me as a sales person, like when I was out at the Baseball Winter Meeting selling my apps, I was actually selling, letting them know about my product. I didn’t enjoy that aspect, but what it boiled down to it all I was doing was talking with people about what I was passionate about. It was never about … I never brought up, “Here’s how much this is going to cost and hey, let me get you to sign these things so we can get you on this list, so we can sell you that.” No, I never wanted to do that. I just talked to them about what I love doing and I think they saw that and that’s what made me more successful than the other competitors in the space, is that it wasn’t about trying to make a sale. It was about, “Hey, let’s talk technology and baseball.”

That’s the thing for me, like all these people who are out there right now trying to pedal like P90X and all these supplements and stuff like that right now, you know what I’m talking about. We all have people in our Facebook feeds and Twitter feeds who are pushing nothing but some nutritional supplement or whatever it maybe, and that’s fine like, “More power to you.” I encourage people to do that type of thing if they want some extra income, but the difference is I don’t want you coming up to me and telling me about how great this thing is repetitively. Sales people don’t get that you aren’t interested, that’s what a sales person is. The sales person does not give up on pushing an idea, that’s what my interpretation of a sales person is, like I go to the car lot, “Let me look at this car.” “Okay, are you going to buy today?” “No,” like, “Leave me alone,” that’s my reply. There’s so many things out there like that right now.

I’m in the South and people try to sell you on their church like, “Do you guys have a church?” I’m like, “Look, leave me alone, that’s a personal thing,” like, “Don’t come at me like that, all right.” I get very defensive, like almost a flight or fight response to sales people, like, “Don’t push anything on me because if you do I’m going to come right back at you.” That’s why, like if I thought of myself as a sales person I would almost like gross myself out from the inside out and implode. But that’s the thing, like if you’re selling something you have to recognize that when somebody’s not interested, read their body language, listen to the words they’re saying, don’t go past the line or keep, “Well, ba-ba-ba-ba-blah for one more day.” “No. Look, I said no, like leave me alone.”

Robert: I think it’s this fine line between being overbearing and being … hustling or being a sales person versus being overbearing. No one has time these days, and that’s what the thing that I found a lot, is that when you’re engaging with people they just don’t have time. If you think about they have a family, they want to get home to their family, they’re focused on their job what they need to get done. If you’re coming at them with all these different things it’s hard for people to engage in those things because they just have so much on their plate. You have to do it the right way. You have to figure out how you can connect and how you can both work together. I feel like that could be a whole another episode talking about that, because that’s an area that I’ve been thinking a lot about because I’m similar to you I’m not a natural, I guess, sales person.

I guess I don’t enjoy as much like closing the deal and things like that, but I do enjoy some of the other things we talked about in the entrepreneurial traits, it’s like identifying those opportunities and really finding ways to solve problems that haven’t been solved before. It’s aligning myself with people that feel the same way and they’re willing to invest in me and my products and my company to help them do that.

Scott: I agree.

Robert: Let’s wrap it up. Let’s just talk about … go through the four traits real quick. Think about these for your own career, your own company, what you’re doing right now and see … think about how they apply to you, maybe how you can, if you’re interested improve in some of these areas, and also think about areas that maybe you’re different and the differences help you as an entrepreneur, they help you as a person, separate yourself from the rest of the pack.
The four of them were that you’re curious, seekers of adventure, learning and opportunity. Entrepreneurs are more comfortable with risks. Entrepreneurs are driven by a need to own products, projects, and initiatives. Finally, entrepreneurs are natural sales people. Thanks for listening and have a great week.

Scott: Don’t be a sales person. Thanks for listening to this episode of The Stretch Goals Podcast. You can access the ShowNotes for this episode and listen to other episodes by heading over to stretchgoals.fm.

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Each week we'll share insights and lessons learned to help you create ambitious goals for your business.

Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.