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The Flip Side of Entrepreneur Traits

I was speaking with an entrepreneur recently and they mentioned their greatest strength can also become their greatest weakness in different contexts.

A.T. Gimbel
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January 15, 2026

I was speaking with an entrepreneur recently and they mentioned their greatest strength can also become their greatest weakness in different contexts. That got me thinking, what are some traits of entrepreneurs that can manifest themselves as both strengths and weaknesses given the situation.

Perfection

A perfectionist can do amazing things building a perfectly engineered product, creating a financial model, or executing an operational plan. But sometimes that can lead to never shipping the product (it is not ready, just one more thing) or not making decisions (doing just a little more analysis to get the “right” answer).

Persistence

Persistence is required as an entrepreneur to fight through all the inevitable challenges and pivots that will come your way. But sometimes persistence to stay with an idea that is not right can lead the entrepreneur to stay too long on something that will never be great, thereby creating a huge opportunity cost from moving on to the next bigger idea.

Relationships

There are some amazing relationship builders that can instantly connect with folks to help with funding, customers, employees, etc. But sometimes people who thrive on relationships have a hard time negotiating deals or making hard decisions on employees as they worry more about ruining the relationship.

These are just a few examples; what are some other entrepreneur traits that have flip sides depending on the context?

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