Cal poses the question after hearing the wondrous story of Dr. Sabrina Kay – who came to the U.S. from South Korea while in college without speaking English, started out as a janitor and began an entrepreneurial journey that took her to the cover of Fortune Magazine.

By the time she'd reached her 30s, Sabrina had amassed enough wealth so that neither she – nor any of her family members – ever needed to work again. But that was only the beginning. Sabrina went on to get a master's degree at USC and a doctorate at the University of Pennsylvania's Wharton School of Business. Now, after buying Fremont College, she's reinventing the entire education system. This episode is packed with takeaways that will make you think about what you would do if never needed to work again.