Dave Kerpen | Turn Your Weakness Into Strength
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Turn Your Weakness Into Strength

Turn Your Weakness Into Strength

When I was 6 years old, I brought home my first math test to my dad. I was excited about having gotten a 99 out of 100, until my dad promptly said to me, “Why didn’t you get 100?”

Two weeks later, I brought my next math test home. I had gotten a 100! Somehow, it still wasn’t good enough. “You didn’t get the extra credit right,” my father told me. “You could have gotten a 104.”

For many years, those moments and others like them have driven me to want more–to be better, and to strive always for perfection and more success. I always want more. I always want to be and do better. If I have start one successful company, I want another. If I have one bestselling book, I want a second, and third. If my team hits a big milestone, I want to hit a bigger and better one ASAP.

Always wanting more and struggling with being satisfied has been a real weakness of mine for many years. But it’s also been a strength, as it’s been, in many ways, the driving force behind successful initiatives.

Last year, I wrote about how to turn weaknesses into strengths. Last month, I asked successful young entrepreneurs, members of the Young Entrepreneur Council (YEC) what their greatest weaknesses are, and how they’ve turned them into strengths. Their answers were honest, vulnerable, and helpful:

1. Naiveté

Being naive can actually be a strength. It prevents you from fearing things you don’t know you need to fear. For example, I tweeted Louisiana’s largest privately owned company’s CEO and set up a meeting through Twitter. I never even knew how big they were until after getting the account. They became my second customer and I didn’t know how hard it was to get their attention until the client told me.

Kenny Nguyen, Big Fish Presentations

2. Finickiness

Being finicky can be annoying in most social settings, however as a founder it is often the catalyst toward entrepreneurship. Founders often don’t want to settle for how things are and want to make things how they should be. This often sparks new products and services that appeal to others like themselves.

Phil Chen, Systems Watch

3. Obsessiveness

Interacting with people who obsess during a social setting can be tiring. Hearing someone talk nonstop about a recent movie or the intricacies of a particular diet plan can get old very fast. But you need to be obsessed to succeed as a founder. To really nail a problem and find a great solution you need to think about it all the time day and night. You need to be obsessed with it.
Charlie Graham, Shop It To Me, Inc.

4.Uncompromising Nature

Being uncompromising can be seen as a weakness, but it’s a quality that can be found in many all-star founders. It’s a quality that won’t allow someone to settle for less in themselves and others. An uncompromising attitude can be the difference between good and great.

Mark Krassner, Knee Walker Central


5. Optimism

Optimists have been proven time and time again to be more successful than pessimists. This is due not to the accuracy of their judgement in any given situation (often the cynical are more accurate), but that they put themselves in more situations to begin with. Optimists see opportunities before others and succeed more. Optimist founders will be more aggressive and visionary.

Brennan White, Cortex

6. Insecurity

While too much of it can be paralyzing, some insecurity, especially when you’re pursuing an audacious strategy, can be beneficial. It drives you to do your best to keep looking over your shoulder, to size up the competition and to honestly acknowledge your weaknesses/limitations so that you can mitigate them.

David Ehrenberg, Early Growth Financial Services


7. Overly Nice
Especially if you are running a service business, being too nice isn’t always a bad thing. Being nice and staying calm under pressure are the best ways to show employees that we are here to serve our customers and clients, even when the going gets tough. There is a time to say no and put your foot down, but being nice first and foremost isn’t a bad position to start from.

Angela Harless, AcrobatAnt


8. Shameless Overconfidence

Someone who’s overconfident to the point of being arrogant is annoying on a personal level, but it’s critical for a founder. They have to believe in what they’re doing at all costs, and shamelessly self-promote their company to everyone in their ecosystem. A strong sense of self helps them keep their vision when they’re surrounded by other talented people competing for the same market.

Dave Nevogt, Hubstaff.com


9. Head in the Clouds

When we imagine the successful founder, it’s someone who can manage products and take initiative. But one blessing in disguise for a founder might be being a bit of a space cadet. Being diligent might be necessary for day-to-day execution, but dreamers often are the ones to come up with the 10x moonshot ideas that more than make up for a lack of diligence.

Brian Honigman, BrianHonigman.com


10. A Wandering Mind

My most creative acquaintances and colleagues hardly ever stop thinking or exploring. This propensity to be easily distracted by new ideas or stimuli allows them to connect two or more seemingly unrelated ideas to create amazing, out-of-the-box solutions and innovations. I wish I could tell my teenage self that sometimes staying super focused at school actually obstructed creativity!

Firas Kittaneh, Amerisleep


11. Jack of All Trades, Master of None

Early in the company’s lifecycle, the founders have a wide range of competencies to cover such as sales, product development, accounting, finance and customer service. Successful founders are able to cover the basics of all of these departments long enough to develop an MVP and acquire crucial early customers.

Faraz Khan, Khan


12. Type A Personality

Having a Type A personality is a weakness that can make one’s life miserable at times, but it does work for an entrepreneur if there is solid vision and you are trying to get somewhere with results by being proactive, laser focused and an organizational freak.


Tolga Tanriseven, GirlsAskGuys


13. Relentless Hustle

Relentlessness or perseverance can be seen as annoying to other people, as we don’t take “no” for an answer. This trait benefits founders though, as we hustle until we get the job done.


Carrie Rich, The Global Good Fund


14. Perpetual Dissatisfaction

While it can make home life difficult, entrepreneurs tend to benefit from the fact that good is never good enough. You hit a revenue goal? It moves higher. Got a product out? You start planning the next one. Your company is doing well? Many of your competitors are doing better. While this perpetual dissatisfaction seems negative, when balanced properly it can result in building great companies.

– Joel Holland, Video Blocks

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