5 Signs Your ‘Problem Child’ Is Actually An Entrepreneur-In-Training

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Today, we call it “buy now, pay later.” But when I was in high school, I just thought of it as easy money.

Those fancy Air Jordans my classmates couldn’t afford? I’d buy them a pair, then let them pay me back in monthly installments. In the end, they shelled out double or triple what I did — but that was just good business, right?

When my school found out, however, they didn’t agree. Combined with some of my other high jinks, my little layaway scheme ended up getting me expelled.  

In hindsight, I realize I wasn’t the only enterprising kid getting in hot water. Like a lot of nascent entrepreneurs, I had ambition, vision, and a strong creative streak. The problem was that’s not how most people saw it. 

Kids like me are still dismissed as problem children for the very qualities that can make them successful in business. It’s time we reframe the conversation. I know from my own life and from mentoring promising young entrepreneurs that these problem traits are assets when they’re channeled constructively.

In fact, research shows many “naughty” children grow up to be successful entrepreneurs. In one 40-year longitudinal study, rule-breaking tweens grew up to earn more money than their studious peers.

As we navigate a shifting economy, climate change, the AI revolution, and continuing globalization we need more contrarian thinkers willing to challenge the rules, not fewer. Here’s how to channel the next generation of “problem” kids.

"Growing up in a hardworking immigrant family, I was no stranger to scarcity, so I looked for creative ways to earn my own money."

Problem traits? Not exactly

I don’t want to glamorize my adolescence. I was definitely a shit disturber. But when I look back, I see that many of my “problem traits” were actually entrepreneurial tendencies waiting to be developed. And I see these same qualities in so many promising young people today: 

Money-focused: Growing up in a hardworking immigrant family, I was no stranger to scarcity, so I looked for creative ways to earn my own money. I won’t lie – many of my hustles weren’t 100% above board, but that’s a typical story among successful entrepreneurs of all stripes — from impresario Jay-Z, who sold drugs in his Brooklyn neighborhood as a young teen, to Warren Buffett, who sifted through litter at horse races, looking for discarded winners.

Risk-tolerant: Like any good entrepreneur, I wasn’t afraid to take calculated risks. I bought fireworks in the U.S. and sold them to kids in the neighborhood, figuring that if I got caught, the punishment would be light. Many successful entrepreneurs show that same kind of risk tolerance. Cybersecurity guru Kevin Mitnick started out as a hacker, for example, before donning the white hat. 

People persuader: I was naturally adept at motivating people, recruiting my friends to go door-to-door selling candy bars (under the guise of a youth soccer team!) and giving them a small cut of the profits. Studies show persuasion is the single most important trait for successful entrepreneurs, greater even than leadership or goal orientation.

Ruthlessly creative: Remember Columbia House music club – where they would send you 10 CDs for a penny? I rented a dozen PO boxes at my corner store, applied for a dozen memberships, then resold the CDs to my classmates at full price. Other future entrepreneurs turned their side hustles into full-time businesses. Sir Richard Branson quit high school entirely to start a magazine.

Contrarian: Another common trait between “problem” kids and entrepreneurs? They’d rather find their own way — one that’s faster, easier, and more profitable — than follow the beaten path. The list of tech titans who dropped out of college testifies to this healthy skepticism of established norms. 

"Look, I know how tempting it is to write off shit disturbers. I remember the looks of exhausted frustration on adults’ faces as they struggled to understand why I couldn’t just behave."

How to channel ‘problem kids’ toward entrepreneurship 

Looking back, I could have easily gone down the wrong path, but several factors helped me redirect my energies. For parents out there today, these simple steps might just help channel your kids’ passions toward entrepreneurship:

First — parents, teachers, advisors — let’s rethink the value of conformity. Research shows that nonconformists are actually more likely than their peers to work for the greater good. As we tackle transforming work environments and overlapping calamities like political unrest, a changing climate, and frustration over social inequality, these free thinkers will be our greatest allies and the next great entrepreneurs. 

But for these restless young learners to thrive, we need to embrace hands-on opportunities like co-ops, technical programs, project-based learning, and ideas labs. After I was expelled, I enrolled in a new school that helped me channel my entrepreneurial energies. Today, programs like Startup Experience, BETA Camp, and Young Entrepreneurs Academy offer hands-on experiences geared explicitly toward helping budding entrepreneurs.

Next, it’s critical to expose kids to mentors who can nurture their talent. I was lucky to have an entrepreneurial uncle who ran a video and electronics store. I’d lend a hand on weekends, and he helped me understand concepts like merchandising, marketing, and customer pipelines. But for kids without family role models, mentorship programs like The Genius School can play the same role.

Finally, all kids – especially precocious rule-breakers – need a firm foundation. I was blessed to know I could count on my mother’s unwavering love no matter how badly I messed up. And, as American Psychologist Abraham Maslow taught us through his hierarchy of needs, people can only thrive if they have the essentials of survival. That’s why I’m a staunch supporter of programs like KidSafe, which provide vulnerable children with resources and support.

Look, I know how tempting it is to write off shit disturbers. I remember the looks of exhausted frustration on adults’ faces as they struggled to understand why I couldn’t just behave. But as we move forward into an uncertain future, it will be the “problem children” who lead the way, challenging old, broken models and creating new opportunities. We can either help them channel their energies toward new ideas and new businesses or stand by and watch.

A version of this article was originally featured in Observer. Keep up with my latest posts by following me here or on Twitter and Instagram.

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