Winners Know It's Always Better to Be the Underdog

Don't swagger if you want to stay on top. Stay humble and grounded.

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By Steve Tobak

Thomas Barwick | Getty Images

Opinions expressed by Entrepreneur contributors are their own.

We all want to be success stories, stars, winners. What if I told you that the best way to get there is to always be the underdog? That adversity and intense competition make us strive that much harder to succeed. And that, if you aspire to achieve great things, competitive spirit is among the most important qualities to have.

Don't let all the negative press about hypercompetitive entrepreneurs like Uber's Travis Kalanick and Amazon's Jeff Bezos fool you. They're not successful in spite of their compulsion to win, but because of it. The same is true of most of the greatest CEOs of our time, from Bill Gates and Andy Grove to Larry Ellison and Steve Jobs.

Related: "An Entrepreneur Needs to Be Both, Humble and Arrogant"

This is not just an American phenomenon, mind you. Softbank founder and chairman Masayoshi Son has a chip on his shoulder as wide as his $85 billion company's global footprint. That's why the boy who once lived with his immigrant parents in an illegal shack is now Japan's richest man. He is never satisfied with what he has.

Related: Why Humble Leaders Inspire Loyal Teams

Likewise, when Lee Kun-hee took over the Samsung Group upon the death of his father, the Korean conglomerate was known as a low-quality producer of low-budget commodity items like food and clothing. That was 1987 when he famously told his staff to "change everything except your wife and kids." Today, Samsung generates 20 percent of South Korea's GDP and Lee is the nation's wealthiest man.

Just last week, Samsung ended Intel's 26-year reign as the world's biggest semiconductor company, but not because the Silicon Valley chip giant is resting on its laurels. On the contrary, the company's leadership still follows Grove's driving principle, that "only the paranoid survive." In his book of the same title, Intel's former chairman astutely observed that "success contains the seeds of its own destruction."

The dominant characteristic among every one of those outstanding leaders is that, even when they were on top, they never felt like they were. They always acted as if they were underdogs fighting bigger and better-equipped enemies on every front. That's what made them winners over the long haul, which is the only timeframe that really matters, when you think about it.

Related: Turns Out, Humility Offers a Competitive Advantage

I can personally attest to the power of the underdog mentality. I spent the bulk of my thirtysomething-year career competing against Microsoft, Intel and Samsung. Those 800-pound gorillas may have dominated their respective markets, but they never gave up a single percent of market share without fighting as if their very existence depended on it.

In one of the greatest business books of all time, What They Don't Teach You at Harvard Business School, Mark McCormack says that true champions are never satisfied with their own accomplishments. They live for the challenge of the next battle, not for the fruits of the last victory. For them, competing and winning is not an event, but a way of life.

Another defining characteristic of super-competitive entrepreneurs is their keen self-awareness: an unabashed openness about their relentless drive for perfection. If that makes them hard-driving a-holes and tough to satisfy, so be it. Flawed as they may be, they make no apologies for who they are. They are their own genuine selves. I've always appreciated that quality. But then, I'm the same way.

Ironically, those who do all the talking about being good guys often turn out to be the biggest creeps. I'm thinking about Gravity4 founder Gurbaksh Chahal, who continued to paint himself as a valiant victim, even after pleading guilty to domestic violence and battery.

Just last week, founder Dave McClure was forced out of 500 Startups over several sexual harassment incidents and a sexual assault claim. In each case, he took advantage of entrepreneurs seeking funding from his startup incubator. In his obligatory apology post titled "I'm a creep. I'm sorry," McClure writes:

"When confronted about what happened, I was at first defensive. I didn't have much empathy for the people I hurt and offended, and rather than face up to my own shallow motivations, I rationalized my actions and came up with reasons to find blame in others, rather than solely with me."

He goes on to say that he ultimately came to realize that he "was the problem," and not "full of goodness and light" as he once thought.

The takeaway is simple: If you want to be a winner, don't act like one. Stay humble and grounded. That's the way to achieve success over the long haul.

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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