On this episode of Redefining Work, I’m joined by David Rogier, founder and CEO at MasterClass. We discuss lessons learned as a founder, how he’s empowering businesses through MasterClass at Work, why education can also be entertaining, and much more.

David became an entrepreneur after a stint in venture capital, where he wasn’t happy. He decided to bet on himself and told his boss he was starting a business — even though he didn’t know what it would be. To his shock, David’s boss promptly offered to invest $500,000. 

Eventually, David leaned into his lifelong love of learning to develop the MasterClass platform, which has more than 180 instructors and classes across a range of subjects. 

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Plan to Fail

With the offer of a $500,000 investment looming over him, David felt pressure to pitch the perfect business idea — but for the first time in his life, he didn’t feel any constraints. “Sometimes I think having a constraint helps you be more creative,” he says. 

What helped him move forward was the ‌advice to build something he'd be proud of — even if it fails. Since David loved learning and realized how important continuous learning was becoming, he decided to design a school with classes that were interesting, engaging and “looked as good as an Oscar-winning film.” From that vision, MasterClass was born in 2015.

One of the MasterClass instructors who’s influenced David immensely is Spanx founder Sara Blakely. “One of the things that she talks about, which is so fascinating, is every night when she was a kid, her dad would ask the whole family, ‘What's one thing that you failed at?’ Because he wanted them to try new things,” David says. 

David loved the concept so much that he applies it at MasterClass: “Every week, we send a note to the whole company of one thing that happened that week … that either myself or somebody in the team failed at, and what we learned from it,” he says.

Learn From What Your Team Is Learning

MasterClass recently launched an enterprise product called MasterClass at Work. This offering provides full access to MasterClass courses, along with tools to help employers understand their teams’ learning needs. Half of the ‌Fortune 100 has adopted the platform, David says. 

One of the most popular classes, David notes, is a sleep science class by Matthew Walker, a sleep expert who is a professor of neuroscience and psychology at the University of California, Berkeley. In fact, one company came to David and said, “Hey, we see the No. 1 class our employees are watching is a sleep science class. Do you think that we have a work-life balance issue?” 

This shows how MasterClass can help employers better understand their workforce — and how they can help workers even when they’re not on the clock.

“I think what firms and companies are starting to realize is that how somebody sleeps at home, how they feel at home, how their mental health is, impacts how that person works,” David says. “And if we can help them there, not only is it good for the company, but also the employee is going to be thankful for it and appreciate that investment and care into themselves.”

Find New Ways to Engage

While there are countless learning platforms, MasterClass' cinematic quality is an essential — and intentional — part of its success. Learning is much harder to engage with when it’s not enjoyable, David says.

“The bar for somebody's attention has risen, and so, whether we like it or not, any L&D content, any educational content, is competing with Tik Tok,” David says. To compete, MasterClass leaned into three key elements: emotion, story, and aesthetics. 

This approach initially confused some inventors. They couldn’t tell whether the platform’s primary purpose was education or entertainment. But that’s the wrong question to ask, David says. 

“The best education is also entertaining,” he says. “And so our hypothesis is, if I can make it really compelling that you want to keep watching it, you're going to learn more. And what we're seeing in the results is our engagement rates are really high.”

People in This Episode

David Rogier: LinkedIn, X (Twitter), MasterClass