Entrepreneurship Lessons From 5 Celebrity CEOs

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It seems like nowadays celebrities get covered in the media from a “business” perspective almost as much as they get talked about for their actual creative work or sports accomplishments. America is a country that values and admires success at the highest levels. We are fascinated by people who can perform at a world-class level in the most competitive human endeavors—and there are lots of crossovers between the worlds of sports, music, and pop culture and the world of business.

Many of the most successful entertainers and athletes are known for managing their careers as if they were CEOs of a corporation. And many of these celebrity CEOs can offer valuable business management lessons—no matter what business or industry you’re in. 

Here are a few insights and lessons from some famous celebrity CEOs:

Bill Belichick

Bill Belichick is the head coach of the New England Patriots, and is arguably the most successful football coach of all time. Belichick has won a record six Super Bowls with the Patriots, and he’s done it—not just with savvy game management and strategic coaching decisions—but with smart moves he makes in the off-season managing the team’s personnel and deciding which players to sign and re-sign to long-term contracts.

Belichick’s genius as a “football CEO” is most apparent in the way he decides which players to invest in, while managing the limitations of the league’s salary cap. He is known for being a football “value investor,” similar to Warren Buffett: he buys low and sells high. The Patriots constantly reload with low-priced young talent, and they are famous for being reluctant to sign high-priced free agents or overpay for talent, even if that means releasing a popular player at the prime of his career. Belichick would rather release or trade a player one year too soon than one year too late; he always wants to keep his options open by finding overlooked, underpriced talent. 

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What does this mean for your business? Stick to your guns on your business strategies. Don’t overpay, don’t get sucked in to the latest fads. Find out a method that works for you, and stay with it.

Bill Belichick has won six Super Bowls, not only because of his generational talent at quarterback, but because he’s a savvy, bordering on “solitary cranky genius,” football mind who resolutely keeps doing things his way—no matter what the rest of the league thinks. People might grumble about “the Patriots Way,” but no other team has managed to replicate their success.   

LeBron James

LeBron James is possibly the greatest basketball player in the game’s history, but his talents and strengths are different from Michael Jordan or other transcendent athletes who were ruthlessly competitive to the point that they sometimes drove people away. LeBron is more like a movie director or ballet choreographer—he uses his influence and his power as a superstar player to bring the right people onto a team and put talent around him, even it means collaborating with his best friends.

What does this mean for your business? When you have leverage, use it. LeBron can often get what he wants from the teams he plays for because he’s so great—even to the point of influencing player personnel decisions or deciding which coach to hire. LeBron has repeatedly made moves to new teams during his career (to Miami, back to Cleveland, to Los Angeles) when he felt it would be more advantageous for him and for the people he cares about. He’s acted more like an entrepreneur than a long-term employee. His lesson: Don’t get bogged down with misguided short-term loyalty—do what’s right for you and be prepared to make a move and assemble a new team whenever you need it.   

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Steven Spielberg

Steven Spielberg has made some of the most beloved mainstream mass-audience movies in American history and loves to play to the biggest audience possible. However, he’s also not afraid to take big risks—he’s made some really violent, gory, but must-see acclaimed movies like Saving Private Ryan and Schindler’s List. 

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