Heartbreak Hill Running Company co-founder Dan Fitzgerald sat down with Cate Brinch of Stoop Sessions, to trace the journey from a single storefront in the South End to a growing national running and fashion brand. Dan shares how his background in competitive running, the surf industry, and how years at Quiksilver shaped the culture behind Heartbreak, and its connection to community, fashion and sport. Together, they examine the story behind the brand’s name, the evolution of its identity, the realities of building a small business, and the lessons learned through setbacks, perseverance, and partnership. The conversation also reflects on the South End’s role in Heartbreak’s growth and how a neighborhood business can carry a piece of Boston across the country.