Innovating Startup Culture

Ben Kaplan sits down with Mark Bertolini, CEO of Oscar Health and former head of Aetna, to break down one of the biggest healthcare turnarounds in recent history.
Oscar Health was bleeding cash, fully dependent on the Affordable Care Act, and struggling to turn a profit. Within just 10 weeks, Mark uncovered $1.4 billion in hidden opportunities, restructured the business, and set it on a path to profitability for the first time ever.
In this episode, Mark reveals:

• Why Oscar’s original founders avoided hiring healthcare experts—and how that nearly doomed the company.
• How AI and large language models cut costs by 1400 basis points.
• The high-stakes reality of running a company that depends entirely on the U.S. government.
• His no-nonsense approach to leadership, from fixing broken businesses to out-negotiating industry giants like CVS.
• What most CEOs get wrong about running a business—and why courage and curiosity matter more than anything else.

This is a must-listen for anyone in business, tech, or leadership, as Mark and Ben break down what it really takes to transform an industry built to resist change.