In this episode, Jeff Shi sits down with Bobby Touran, the two-time founder and CEO behind leading insurtech startups Pathpoint and Rainbow. Bobby shares his journey from building software-driven companies to founding two specialized underwriting and distribution platforms within the commercial insurance space. Hear how Bobby transitioned from the world of engineering-led startups into surplus lines brokerage and eventually launched Rainbow—a software-enabled underwriting company focused on niche commercial markets like restaurants and wellness.