MasterClass CEO David Rogier: ‘What Is Your Best Failure?’

The online learning platform that David Rogier founded and now heads up as CEO features some of the world’s most talented people who share and preserve invaluable knowledge and stories so future generations can access and appreciate them. Where else can you learn about humor from Kevin Hart, the runner’s mindset from Joan Benoit Samuelson or chess from Gary Kasparov?

You would think that working with all this world-class expertise would rub off on Rogier’s leadership style. And guess what? You would be right. For example, in her class on MasterClass, instructor Sara Blakely, the self-made billionaire founder of Spanx, tells the story of how her father tried to make it acceptable to try things and fail by asking family members at dinner every night, “What is something that you failed at today?”

Rogier loved this idea so much that every week he followed suit, sending out a company memo talking about MasterClass’s “best failure” of the week. Rather than dreading their boss’s memo, Rogier’s team came to look forward to hearing about the things each failure taught the team and why Rogier was so proud and impressed by them.

“The only way that you are going to discover new things and do big, cool, new things is you are going to have to fail at them,” Rogier explained in the podcast. “You get back up, learn from it and go and build the next thing.”

In the podcast, Rogier demonstrates a particular penchant for showing how leaders can build not only high-performing but also courageous cultures based on shared values and expectations. Topics include:

• 5:00 – The extraordinary lesson about education passed down to him by his grandmother, a Holocaust survivor and inspirational figure behind MasterClass.
• 10:00 – Behind-the-scenes stories of the first three signings: Serena Williams, James Patterson, and Dustin Hoffman.
• 20:00 – How Mike Krzyzewski, Duke basketball’s legendary Coach K, implemented his “left-handed question” technique to encourage difficult conversations. 
• 25:00 – The difference between what people say they want and what people actually want based on their actions—and why you need to measure both.

Only a second-grader at the time of his conversation with his grandmother, Rogier nonetheless remembers it as if it happened yesterday. “And I think that pushed me to probably be more curious to want to learn more and ask more questions,” he recalled. “But it also pushed me, when I had the chance to build a company, to try to do that same thing, which is remember you are not suffering. Be okay and take that as a gift to yourself.”