On the Flip Side: The 8 Paradoxical Traits of an Entrepreneur

Jody Porowski
Sep 13, 2014 · 4 min read

I’m convinced that developing, marketing, and growing an Internet consumer product is one of the most amazing experiences a person could ever have.

Creating something from nothing and watching other people use it, love it, and share it is simultaneously the most empowering and humbling feeling. The satisfaction that comes from watching numbers climb as you tweak and improve your product is indescribable. The exhilarating triumph you feel each time you solve an unsolvable problem is your very own version of winning the lottery. And the relief that floods over you when a risky decision pays off mirrors a brush with death and results in similar feelings of invincibility and extreme gratefulness.

When it comes down to it, there is no one perfect word to describe the bizarre experience of being an entrepreneur. Call it love, call it an addiction, whatever you want to call it, I’m hooked.

On the flip side, I’m also convinced that developing, marketing, and growing an Internet consumer company is one of the most challenging, frustrating and painful journeys one could possibly choose to embark on. The marketplace for consumer platforms is insanely crowded and the expectations from users are astronomical. Without recounting every excruciating detail, let’s just say that the highs are closely rivaled by the lows.

A rollarcoaster of highs and lows. All-consuming, and never-ending. Who would ever choose that job? And who could possibly succeed in such role? It turns out that the personality traits of successful entrepreneurs are indeed, by necessity, complex.

  1. An entrepreneur needs to be stubborn yet flexible. They need to be stubborn enough to believe in their own idea when no one else does. But at the same time, an entrepreneur needs to be flexible enough to change routes when necessary. It will often be necessary.
  2. They need to be confident, yet humble. Confident enough to move forward alone, but humble enough to ask for help. Because no one can do it alone. They should be confident enough to stand before world leaders and humble enough to spend hours entering data into spreadsheets and making cold calls from their home office.
  3. They should be a big-picture visionary, yet detail-oriented. An entrepreneur needs to live in the future— a future that, frankly, doesn’t exist yet. Their heart is in the future but their mind is in the present. They meticulously craft and execute a detailed plan, because they know that the imaginary future they dream of won’t happen if they don’t make it happen.
  4. They can convince anyone of anything, but choose to tell the truth. Because there’s nothing more convincing and enduring than truth. It’s an entrepreneur’s job to believe so deeply in their company and to convince others to believe in it too. An entrepreneur knows that when people believe you and believe in you, they become your greatest partner.
  5. An entrepreneur needs to be kind, but firm. Kind enough to attract others to their team, but firm enough to maintain control. An entrepreneur should understand that well-loved people are loyal people. But they also need know that people need a leader. And a leader’s job is often to make hard decisions for the good of the group.
  6. Speaking of relationships, an entrepreneur needs to care what people think, but not too much. They need to involve others in the process of building the company. And they need to understand the value of positive press. But they can’t be a people pleaser. They can’t be ruled by the opinions of others. There’s no more likely death sentence than an entrepreneur who’s swept into the dangerous current of others’ opinions.
  7. An entrepreneur needs to be independent yet teachable. Their job is to have an opinion about every detail, while simultaneously realizing they don’t know everything. Companies face tremendously huge decisions every day and it’s the leader’s job to make a final call. An entrepreneur should understand the gravity of this role and be wise enough to seek council.
  8. They need to embrace risk while simultaneously preventing it. An entrepreneur needs to be able to dive headfirst into the unknown. Anxiety switch: OFF. Adventure switch: ON. But no matter how adventurous you might be, you have to admit that entrepreneurship is risky business. A successful entrepreneur is a trustworthy daredevil. They understand that the greatest derisker of all is a backup to a backup.

While I believe the eight paradoxes that I listed above increase an entrepreneur’s chance of success, I don’t think most entrepreneurs take the time to see if they “fit the mold”. Entrepreneurs are simply people who believe in an idea and who take it upon themselves to make the idea a reality. And therein lies the key to survival which is often the key to success.

An entrepreneur who believes in their mission soon realizes, as many others have learned before, that belief is a powerful force. You can’t deny it. You can’t hide from it. And it’s not easily snuffed out by fear, mockery, disappointment or failure. Belief doesn’t mean you won’t die, that your company won’t fail. But it does give you something worth failing for. And more importantly, it gives you something worth fighting for. Here’s to those who are brave enough to believe.


Jody Porowski is the Founder and CEO of Avelist. She likes being an entrepreneur and she likes her company even more. Check it out at www.avelist.com. And feel free to say hi on Twitter @jodyporowski. She likes meeting new people.

TheLi.st @ Medium

Worth your time.

    Jody Porowski

    Written by

    daughter. sister. friend. previous ceo/founder avelist. current product at the muse. writing at jodyporowski.com. tweeting @jodyporowski.

    TheLi.st @ Medium

    Worth your time.

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