“I love the classic definition of the entrepreneur,” declared Jim Twining, a seasoned CEO and entrepreneur who was also a partner in the apparel company Southern Tide. “The one I like is ‘a person who organizes and operates a business, taking on greater than normal financial risk in order to do so, doing it in spite of the odds, in spite of the fact that some people might think they’re crazy.’” Though not part of that classic definition, he added, “Many of them have this unbelievable drive to succeed.” Having straddled both the corporate and entrepreneur side of business, Twining brings great perspective to not only what defines an entrepreneur, but what is needed for an entrepreneur to succeed in often fluid environments lacking boundaries.

Some quick background notes on Twining for context. He has worked in start-ups and in very large companies such as GE. He spent 18 years in the software business, the last five as CEO of a 170-person software company, which was sold to a PE firm. In 2005 he founded his own consulting business. Then in January 2008 he became Managing Member and CEO of Southern Tide, a startup apparel company, which they sold in 2013. During his tenure, among other accolades, both Inc. and Forbes recognized Southern Tide for its growth and promise. Today, he is back into consulting, mentoring, and Chairman of Ledbury, a luxury shirt maker and sportswear brand – so safe to say the guy has a range of experiences to draw upon.

Who Makes a Good Entrepreneur?
Building off the above concise definition of the entrepreneur and knowing he’s mentored dozens of entrepreneurs, we asked Twining if there were certain personality types that might better succeed as an entrepreneur. Certainly, on a superficial level, pop culture would lead you to believe that they’re curious, creative, confident, decisive, high-octane rock stars. However, we couched our question in the more basic terms of a meticulous planner versus someone who goes with the flow or by feel. “I think we have to be careful with that personality assessment, and what works and what doesn’t work best,” he answered, “because I think in certain circumstances the more deliberate, the more organized a person is, or the person who uses a lot of foresight and planning in their life, could be much more effective than the guy who is shooting from the hip.”

From his experiences, Twining explained that entrepreneurs truly run the gamut of personality and modes of operation. There are those at one end who are “easily adaptable, can adjust to any situation, are quick on their feet,” as well as perhaps not being that organized and going more by feel. At the other end of the spectrum are those “not as adaptable or comfortable with change” and who might even get nervous if they don’t know what they’re doing for lunch the next day. Of course they can be extroverts but they could also be super introverted or super anal individuals who would rather be shut off from the world. In other words, they don’t fit that stereotypical image of a swaggering entrepreneur who’d love nothing more than to get on Shark Tank and strut their stuff.

“But that second kind of person,” Twining added, “let’s say you put them in a biomedical start up where research is critical, where you must endure a long drawn out, step-by-step FDA approval process, or there are significant technical hurdles in place, and that kind of person might be great. I guess what I’m saying is that there are different types of businesses and industries out there and there’s potentially something for everybody.” So, personality type does not limit success; however, Twining clarified that doesn’t mean there is entrepreneurial opportunity for everyone.

Across the spectrum of personalities, there is one trait Twining finds exceedingly important: resourcefulness. Again based on his experiences, he said, “Resourcefulness is one of if not the most important trait of successful entrepreneurs that I’ve worked with. The ability to always find a way to get done what needs to get done. To find that capital, that source for manufacturing or raw materials, to find the answers to things they’ve never dealt with, to find that resource that can help them through a situation they can’t figure out. It’s the determination to get things done even when they have no idea how to do it.”

Self-awareness and Modifying Your Behavior
Digging a little deeper into personality and behavior, we asked Twining about the self-awareness factor and how it might impact success. Has he seen different levels of self-awareness in the entrepreneurs he has mentored? “Sure I have,” he answered without hesitation. “Those who are really self-aware and have empathy, true empathy, and they have emotional intelligence, and they understand what’s going on around them, I think, have a much better chance of being successful in any endeavor than those who don’t. There are many ways people can become better at that, by reading, talking to people who understand it, opening up a little bit, and having somebody call you out when they need to.” He did add that of times he has tried to help a person with their self-awareness, it was very challenging for them and it usually didn’t result in dramatic change. But in a few instances, the change was very positive. Twining notes that some of this often comes with maturity and experience.

So this raises the question of whether anyone and everyone can truly improve their self-awareness and emotional intelligence as articles in the popular press would lead you to believe. A critical personality trait behind both is empathy, so we asked Twining whether he thought empathy is something you are born with or not. Is it innate or learned? Before answering, he acknowledged he’s no expert in this area, but has spent a lot of time talking to and learning from those who are experts. He also offered the caveat that his thoughts on it are based on his experiences and what he has learned from some of those resources. “I am a big believer in innate versus learned behavior for the deepest parts of our personalities,” he said. “My opinion is pretty steadfast that you are born with what your natural personality is. Of course experience can bring about different behavior without changing the underlying personality, and I do think intellect can help a person because to me the ability to assess, understand and process cause and effect can contribute to self-awareness. A person who is smart, might figure things out, and when they realize I’m this way, they can try to modify their behavior to not be that way as much. They’ll probably always have to fight it. I do. There are things about me that I realized in my mid-20s by having some pretty good mentors who shot straight with me and coached me. For years I really had to work on it but I think I’m a little bit better now.”

As for an example of what he has tried to modify, Twining explained, “My sense of urgency in situations where it wasn’t required, where it might even be off-putting. Also, not being as concerned with what’s important to other people, and a little bit too self-focused, if that’s the right word. I tried to be much better at understanding what the whole playing field looks like, instead of just my little box on the playing field.” He added that self-focused people who do not change or modify their behavior “can be sole producers in a business, but they’re not often going to build an organization and lead for very long. They just won’t attract the right kind of people, and over time talented people will leave. So I was taught that and took it to heart. Perhaps one of the biggest influencers on my life related to this issue was Zig Ziglar. He wrote, ‘People do not care how much you know, until they know how much you care.’ That quote had a profound impact on me and is a constant reminder that I rely on.”

Stay tuned for Part Two, which addresses the lack of boundaries in the entrepreneurial environment, the fatigue factor, and potential conflicts to be ready for!