Hosts Jacob Goldstein and Robert Smith trace the rise of Southwest Airlines from a Texas intrastate startup sketched on a cocktail napkin to one of the most consistently profitable airlines in U.S. history. They explain how regulatory structures, low fares, aggressive legal battles, operational innovations, and a deliberately unglamorous business strategy gave Southwest a durable edge in a notoriously bad industry. The episode then examines how those same strengths later exposed vulnerabilities, culminating in the 737 MAX grounding, a holiday meltdown, activist investor pressure, and strategic changes like adding assigned seating.