The Reboot Podcast

For leaders, navigating the roller coaster experience of entrepreneurship can be flat-out exhausting. The constant fluctuation of riding highs and surviving lows often leaves little time for reflection, much less appreciation for how far you’ve come. But what if there was a different way? What if you didn’t have to ride the rollercoaster at all? In this episode, Jerry sits down with Jean Smart, founder and CEO of Penelope, a retirement savings platform exclusively for small business owners and their employees. Jean describes how growing up as a child of Korean immigrants and watching her parents struggle to save for retirement served as the impetus for creating Penelope. She reflects on the responsibility she carries to be a good steward of her business and the new weight she feels to represent Asian women in the fintech space. Jerry urges Jean to return to the question, “Why do I do what I do?” when things get overwhelming, and provides guidance for how to view the rollercoaster from the ground versus strapp