A Balancing Act: The Characteristics That Differentiate Successful Entrepreneurs

Janet Bannister, successful founder and Real Ventures partner shares 4 practical pieces of advice every striving entrepreneur needs to hear in 2019

Real Ventures
Real Ventures


By Janet Bannister

Photo by Henry Lim on Unsplash

As a VC and former founder and operator, I am often asked what makes a great entrepreneur. What are the qualities that set successful founders apart? Are there personality traits or characteristics that differentiate the best performing entrepreneurs from the average?

After being asked this question enough times and listening to other people’s answers, I noticed that too often, people will recite one word, the one quality that they think is key to success. But the answer is not as simple as one word. Too often, people are told that if they just, for example, “persist”, they will be successful. While persistence is critically important, it is useful to think about what persistence really means — and doesn’t mean.

The right “type” of persistence

There’s a famous quote that the definition of insanity is continuing to do the same thing and expecting different results. Often, entrepreneurs continue to do the same thing, despite that “thing” not working, driven on by the belief that they must be persistent if they are to succeed.

Yes, you need to be persistent, but persistence doesn’t mean you should keep doing the same thing if it is not working. It doesn’t mean you should just keep calling the same type of prospects with the same offering if those customers are consistently rejecting it. Persistence means that you need to keep going, but you need to marry that with rapid iteration, quick understanding and agility.

As important as persistence is, success is not a matter of one single trait, and even if it were, there is often a dichotomy in the conventional wisdom that founders hear, leaving them to question themselves and what they should be doing. Below I have laid out three of these dichotomies and some suggestions on how to think about these conflicting messages.

Working hard vs. work-life balance

While founders are often told that they need to work hard and put in long hours and late nights, they are also told that they need to take care of themselves and have some sort of work-life balance in order to be able to bring their “best selves” to work.

In my experience, having seen founders both excel and stumble, the answer lies in a balance between the two and most importantly, the answer lies in ruthless prioritization, executing with excellence on the things that are important, and being extremely disciplined and efficient with how you spend every minute of your time.

I also strongly believe in the importance of making time to exercise daily, get enough sleep, and eat well so that you can bring a high level of energy, focus and drive to each one of your working hours.

Generalist vs. specialist

In the early days of building a company, founders need to wear several different hats, including Engineering, Product, Sales, Marketing, Customer Service, Finance and HR. This can lead to founders feeling pressure that they need to be proficient at everything. On the flipside, there are many people who tell founders that they need to be “spiky” — that being really good at one thing is what’s most important.

The reality is that building a company is not an individual sport; it’s a team sport. Therefore, two of the most important skills for any founder CEO are self-awareness and the ability to attract and lead people who will complement their skills.

I often tell founders that it is not their responsibility to do all the work nor to solve all the problems, but it is their responsibility to make sure that the work is done extremely well and that the problems are effectively solved. Building a company is about putting the right team in place and ensuring your employees are aligned, motivated and working together effectively.

Confident vs. humble

The stereotypical, supremely confident entrepreneur, popularized by images of Steve Jobs, Elon Musk, Richard Branson and others, often leads founders to believe that in order to be successful, they must project an unfailing sense of self-assurance. And yet founders are also told that they need to listen to others, delegate appropriately and be a caring leader. How to reconcile the two?

I have noticed that the most effective leaders are confident yet humble: they believe in their ability to be successful but know that success will be predicated upon building a strong team that works effectively toward a common goal. They are confident enough to believe that their vision can become a large, successful business and are able to sell that vision to others, yet they are humble enough to recognize that they have a lot to learn, and a lot of growing to do to achieve that vision and are therefore a “sponge for learning.” They also have enough confidence and humility to be authentic, to own up to their mistakes, and to treat feedback as a gift.

In reflecting on these things, I am reminded of the quote by Mr. Miyagi in the Karate Kid movie (which we watched yet again over the holidays): “Balance is key. Balance good — karate good. Everything good. Balance bad — better pack up, go home.” Ultimately, that is the message. Becoming a successful entrepreneur requires that you balance often opposing skill sets. By being reflective, values-driven and focused on getting better every day, you can and will strike the right balance.



Real Ventures
Real Ventures

Canada’s leading early-stage VC firm dedicated to serving entrepreneurs and nurturing the communities in which they thrive.