Confessions of a Serial Entrepreneur

Mario Schlosser, CEO, and co-founder of Oscar Health helped redefine the health insurance category by using data to give members better customer experiences and thus improved patient outcomes. He dared to use emerging technologies in a heretofore technologically timid industry – an approach that was disruptive, transforming, and highly successful.

Like many of our guests, Mario’s path to Oscar Health wasn’t a direct one. A lot of success in a lot of disparate industries. But what didn’t make it on Mario’s resume—yet had a valuable impact on his leadership and entrepreneurial approach—are the startups Mario founded that failed. Because it’s how he’s learned to avoid mistakes – by actually giving himself permission to make them. See what works, see what doesn’t; and learn from it all.

In this episode, Mario elaborates on this and other insights relating to his success as a leader, including the importance of people matters, the reality of luck, and why paying attention to little nudges along the way can take you in new, totally amazing directions.