Does Being A Natural Troublemaker Make You A Great Entrepreneur?

In search of data to answer a fascinating question

WASHINGTON, DC – MAY 30: Tesla CEO Elon Musk speaks alongside U.S. President Donald Trump to reporters in the Oval Office of the White House on May 30, 2025 in Washington, DC. Musk, who served as an adviser to Trump and led the Department of Government Efficiency, announced he would leave his role in the Trump administration to refocus on his businesses. (Photo by Kevin Dietsch/Getty Images)

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Famous stories of mega-successful entrepreneurs with a rich history of rebellious, contrarian, and even antisocial behaviors are so numerous that, to the general public, they are closer to signaling the norm than an exception to the rule.

Famous stories include Rockefeller, Henry Ford, Peter Thiel, Bill Gates, as well as Steve Jobs, whose legendary success was built on a cocktail of rule-breaking, mercurial outbursts, and open disregard for social norms. Travis Kalanick, whose confrontational leadership style at Uber helped the company explode in value while triggering a global governance crisis. Jeff Bezos, whose early-stage mantra of “disagree and commit” masked a famously intense, often intimidating management approach. Elon Musk, whose impulsive, combative, and norm-defying persona has become almost a caricature of entrepreneurial extremity. One could add Larry Ellison (a mentor to both Jobs and Musk), long known for his ruthless competitiveness and “win at any cost” ethos, or Ingvar Kamprad, the IKEA founder, who openly admitted to a youth spent in rebellious and sometimes delinquent behavior.

Of course, not all wildly successful founders fit the rebellious or antisocial stereotype. Many of the world’s richest entrepreneurs are known precisely for their calm, disciplined, and prosocial reputations. Warren Buffett built Berkshire Hathaway through patience, modesty, and an almost pastoral sense of steadiness. Phil Knight, despite founding one of the most aggressive brands on earth, is remembered by colleagues as shy, loyal, and quietly generous. Reed Hastings transformed Netflix through curiosity, humility, and a famously adult culture rooted in trust rather than dominance. Brian Chesky (Airbnb) and Whitney Wolfe Herd (Bumble) became synonymous with empathetic, design-driven leadership. And Sara Blakely, the youngest self-made female billionaire in the U.S., is known not for rule-breaking theatrics but for optimism, gratitude, and a near-pathological politeness.

To be sure, no one of these founders are saints (everyone has a dark side) but their public reputations and long-standing patterns of behavior contradict the idea that entrepreneurial success requires abrasiveness or aggression. If anything, their stories illustrate how far kindness, emotional intelligence, and long-term discipline can take someone in the entrepreneurial arena, challenging the cliché that only rebels and contrarians build empires.

At the same time, the catalogue of entrepreneurs whose trajectories include arrogance, rule-breaking, defiance, and even outright antisocial tendencies is extensive enough that, to most people, it feels closer to the template than the exception. These stories dominate popular imagination precisely because they are dramatic, unconventional, and glamorous; and because they reinforce the seductive myth that success is created by people who refuse to play by the rules.

Indeed, if the average human is asked to think of a typical entrepreneur, they will be unlikely to come up with a person who exemplifies the value of bright side traits, such as conscientiousness, emotional intelligence, agreeableness, and emotional stability as predictors of career success – something that, at least, holds true for the general population.

Then again, most people in the world are not entrepreneurs (especially in the developed world, where formal job opportunities reduce the incentives to start your own business), and even fewer are actually successful entrepreneurs. The data on this are well-known and rather consistent over the past few decades: that is, when people decide to work for themselves, they will end up working longer hours to earn less and contribute less to the wider economy than when they are employed by someone else, whether that’s a medium size organization or a multinational corporation.

Since stories sell but data tell, it is instructional to examine the science of personality and entrepreneurship, particularly findings published in independent peer-reviewed journal articles, to get a better, evidence-based sense of the degree to which counterproductive personality characteristics may actually help entrepreneurs with their ventures.

In a recent study, researchers examined which personality traits predict entrepreneurial tendencies, and the findings offer an important counterpoint to the stereotype that successful founders must be abrasive, rule-breaking, or high on dark-side traits. The study showed that the strongest and most consistent predictors of entrepreneurial propensity were actually bright-side traits: openness to experience, conscientiousness, and extraversion.

In fact, openness emerged as the single most powerful predictor of entrepreneurial tendencies, followed closely by conscientiousness, a trait far more aligned with discipline, reliability, and long-term thinking than with disruption for its own sake. Entrepreneurial potential was also associated with emotional stability and agreeableness in simple correlations, underscoring that curiosity, diligence, and sociability play a larger role in entrepreneurial motivation than people tend to assume. In essence, then, there is no systematic personality difference between successful entrepreneurs and successful employees or leaders.

Although the dark-side traits attract most of the media attention, the study found that only narcissism and psychopathy showed modest independent effects, and even then these explained a small share of the overall variance relative to the Big Five. Narcissism’s positive association with entrepreneurial tendencies was expected (confidence and charisma often accelerate opportunity recognition) but its effect was nowhere near as large as that of openness or conscientiousness. Machiavellianism, despite its pop-culture association with entrepreneurial cunning, did not significantly predict entrepreneurial tendencies in the full model.

Taken together, the results suggest that entrepreneurial aspiration is better explained by imagination, effort, sociability, and cognitive flexibility than by ruthlessness or antisocial tendencies. In other words, many highly successful founders do not conform to the mythology of the mercurial disruptor or the lovable villain; instead, they embody the quieter profile highlighted by this study: curious, hard-working, socially attuned, emotionally steady individuals whose success stems from psychological strengths rather than dark-side theatrics.

In the end, the entrepreneurial world is far less of a comic-book universe than popular imagination suggests: there are no personality “superpowers,” just different combinations of human traits that can be channeled productively or destructively. The research shows that what truly fuels entrepreneurial ambition is not the outlaw mindset or the performative bravado that dominates founder mythology, but the quieter virtues we tend to overlook: curiosity, discipline, emotional steadiness, and the social skills required to bring others along. The irony is that while the loudest stories celebrate volatility, the data points toward stability; while folklore lionizes the rebel, success more often belongs to the builder. And perhaps that is the real entrepreneurial lesson: you don’t need to be a pirate, a prophet, or a provocateur to create something great — just someone willing to imagine a better world, and above all persist in your crazy aspirations in order to turn them into a better reality for all.

So, does being a natural troublemaker make you a great entrepreneur? The short answer is: probably not. For every rule-breaker who builds a unicorn, far more end up unemployed, underperforming, or (in extreme cases) incarcerated rather than innovating.

The data are unequivocal: the traits that reliably predict entrepreneurial drive are not defiance, volatility, or antisocial tendencies, but openness, discipline, sociability, and emotional steadiness.

Sure, a touch of rebelliousness may help challenge conventions, but it is hardly the engine of sustained entrepreneurial success. If anything, the science suggests that the founders most likely to thrive are not the troublemakers who ignore the rules, but the curious, conscientious builders who rewrite them with purpose.