10 Traits of Successful Entrepreneurs That Investors Love (Even If They Seem Like Jerks)

The author Dima, is the founder of PitchBob.io, an AI co-pilot for entrepreneurs. They are developing a product that will positively impact entrepreneurs’ success.  This drives him to constantly study the factors that can increase the likelihood of entrepreneurial success. Most investors emphasize the primary importance of the team and the founder yet rarely specify which qualities they deem essential.

He became intrigued by the idea of analyzing this factor in investment decision-making and comparing the traits of globally renowned successful entrepreneurs with those of people in everyday life who have not yet achieved significant success. This exploration aims to uncover patterns in character and behavior that might distinguish proven success from untapped potential.

After reading the biographies of Elon Musk, Steve Jobs and many other successful entrepreneurs, he noticed a recurring theme: Many of them weren’t what we’d call “pleasant” people in the conventional sense. Perhaps their success reframes our perception of their behavior, but it raises a thought-provoking question:  Do you need to be a jerk to succeed as an entrepreneur, or is it just a side effect of the intense demands of building something extraordinary?

The truth isn’t black and white. Many approachable, genuinely kind people achieve entrepreneurial success, yet a pattern of distinct — and sometimes abrasive — traits is undeniable among high achievers. Investors, whose livelihoods depend on betting on the right founders, often recognize these traits as essential indicators of resilience and determination.

Here are ten such traits that may brand an entrepreneur as either a jerk or a visionary leader, depending on perspective. Whether you choose to embrace, avoid or adapt them is entirely up to you.

1. Unbounded pragmatism.  Startup founders thrive where others see limitations. They navigate bureaucracy, uncover loopholes and adapt to challenging circumstances. Their ability to creatively solve problems without breaking ethical boundaries allows them to succeed where others falter.  Why investors love it: Pragmatism signals resourcefulness and the ability to adapt, both critical in overcoming the inevitable roadblocks of entrepreneurship.
2. Arrogance.  Entrepreneurs must believe their ideas can change the world. While arrogance can alienate people, it also fuels the confidence needed to push forward when no one else believes in their vision.  Why investors love it: Confidence — bordering on arrogance — convinces others to believe in the founder’s vision, attracting customers, partners and investors.
3. Strategic selfishness.  Entrepreneurs prioritize their goals over everything else, sacrificing weekends, personal time and sometimes even relationships. This focus ensures that nothing distracts them from building their vision.  Why investors love it: Dedication to the mission reassures investors that the founder is fully committed, reducing the risk of abandonment.
4. Assertiveness bordering on rudeness.  Entrepreneurs know how to push boundaries and demand what they need. Their ability to navigate tough negotiations and secure resources sets them apart, even if it occasionally comes off as impolite.  Why investors love it: Assertiveness leads to results. Investors value founders who can secure deals and fight for their startups in competitive environments.
5. Risk-taking without overthinking.  Charging ahead without overanalyzing risks can lead to breakthroughs. Entrepreneurs who take decisive action often uncover opportunities others overlook.  Why investors love it: Risk-takers are more likely to achieve extraordinary outcomes. Balanced with a willingness to pivot, this trait can be invaluable.
6. The art of charm.  Entrepreneurs master the art of persuasion. Whether convincing an investor, inspiring a team or closing a partnership, charm is a strategic tool they wield effectively.  Why investors love it: A charismatic entrepreneur can rally stakeholders and secure their startup’s resources to thrive.
7. Hyperactivity.  Entrepreneurs constantly switch between ideas and tasks, pursuing opportunities at lightning speed. While many ventures may fail, their energy ensures that at least one will stick.  Why investors love it: Hyperactivity reflects a relentless drive to experiment and find what works, a critical trait in the iterative world of startups.
8. Low empathy.  Entrepreneurs often lack time to dwell on others’ emotions. Their focus on achieving their goals can come across as cold, but it enables them to make tough decisions without hesitation.  Why investors love it: This focus ensures that founders prioritize results over distractions, making them more effective leaders.
9. Contradictory nature.  Successful entrepreneurs adapt constantly, sometimes contradicting their earlier decisions. They view this as flexibility, allowing them to pivot as circumstances evolve.  Why investors love it: The ability to adapt quickly to changing market conditions increases a startup’s chances of survival.
10. Selective forgetfulness.  Entrepreneurs have an uncanny ability to “forget” past failures, enabling them to press forward with optimism. This resilience keeps them motivated and inspires confidence in others.  Why investors love it: Selective amnesia allows founders to focus on the future and learn from failure without dwelling on it.

Resourcefulness above all.  Entrepreneurs don’t take “no” for an answer. When faced with closed doors, they deconstruct obstacles, improvise solutions and tap into their networks to find a way forward. This resourcefulness defines their approach to challenges.

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