The story of Payless ShoeSource is a cautionary tale of a retail giant that failed to adapt to changing market trends and technological advancements. Founded in 1956, Payless revolutionized the shoe industry with its self-service model, offering a wide range of affordable shoes to families. The company expanded rapidly, and by the 1970s, it became the largest family shoe store chain in the US. However, with the rise of e-commerce and changing consumer preferences, Payless struggled to stay relevant. Despite efforts to revamp its brand and online presence, the company filed for bankruptcy twice and eventually closed over 2,100 stores in the US and Puerto Rico. The Payless story highlights the importance of adaptability, innovation, and staying ahead of the curve in the rapidly evolving retail landscape. Through interviews and research, this episode of Tech Tales Found dissects the reasons behind Payless's downfall and what lessons can be learned from its mistakes. From the impact on employees and local communities to the shifting retail landscape, this episode offers a nuanced exploration of the intersection of technology, business, and human connection.