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Success doesn’t kill insecurity—even billionaires and Oscar-winners beg for feedback between takes, MasterClass CEO says

Preston Fore
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Preston Fore
Preston Fore
Success Reporter
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Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
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November 8, 2025, 8:10 AM ET
David Rogier
Even after becoming a CEO or Hollywood star, the drive for improvement is embodied among the most successful people, according to MasterClass CEO David Rogier.Lauren Justice/Bloomberg via Getty Images

What do CEOs, NBA stars, and Hollywood’s elite all have in common? At first glance, not much.

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However, despite coming from vastly different worlds, they all share one powerful trait: an unrelenting desire to get better. That’s at least according to David Rogier, the CEO of MasterClass—an online learning platform, valued at $2.75 billion in 2021, where celebrities and industry leaders teach everything from cooking and acting to entrepreneurship and content creation.

Rogier said no matter how big one’s net worth or trophy case is, the most successful people on his platform strive for feedback—and they’re not shy about asking for it.

“I thought when you’re on top of the game, maybe you don’t, but like every single one of our instructors, every time you cut the camera, ask: What things went well? What things did not? What can they improve? Even people who are MVPs, All-Stars, have won Oscars, Emmys, Grammy awards still ask for notes and feedback,” Rogier told Fortune.

MasterClass’s roster of celebrity instructors includes names like Mark Cuban, Richard Branson, Stephen Curry, Kris Jenner, and Samuel L. Jackson—all known for success in vastly different areas. But when it comes to growth, Rogier said, they’re all the same: “I was shocked at not only how hard these people work, but that they crave feedback.”

Throughout their careers, Rogier added that high achievers often share one superpower that has become more critical than ever: the ability to learn on the fly.

“Your ability to learn things fast is now probably the most important skill,” the 42-year-old said.

Be comfortable with not knowing something

At a distance, emulating the success of household names can feel like a herculean task. But Rogier, a Los Angeles native who later obtained his Stanford MBA, insists it’s not as complicated as it seems—so long as you’re willing to step outside your comfort zone.

“When you don’t know something, it is scary. You are gonna be judged for the first time on it,” Rogier said. “But in that process, you have to train yourself. It is also like a confidence thing to go and actually, when I don’t know something, to take that discomfort and go chase it.”

That willingness to embrace the unknown, Rogier said, often separates those who reach the top from those who plateau along the way. British race car driver Lewis Hamilton, one of MasterClass’s most popular instructors, puts it this way: if the path to success were easy, someone else would’ve already done it.

“If you go on a training bike, and you’ve got it in the first gear—and you’re not getting any resistance, there’s no feedback, it’s easy—you’re not challenging yourself,” Hamilton said in his MasterClass course. “I think you’ve got to set goals and targets that you can almost think that, ‘Geez, that’s not possible. How am I going to get there?’”

For Hamilton, setting challenges—even when they seem out of reach—helped cement his career trajectory. As early as age 10, he reportedly wanted to be a Formula One driver. By 21, he became the sport’s youngest champion, and he’s since secured his place among the greatest drivers of all time.

At the Fortune Workplace Innovation Summit, Fortune 500 leaders will convene to explore the defining questions shaping the workforce of the future—delivering bold ideas, powerful connections, and actionable insights for building resilient organizations for the decade ahead. Join Fortune May 19–20 in Atlanta. Register now.
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Preston Fore
By Preston ForeSuccess Reporter
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Preston Fore is a reporter on Fortune's Success team.

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