In this episode of South End Stoops, Cate Brinch sits down with Dan Fitzgerald, co-founder of Heartbreak Hill Running Company, 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 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.

Key Points From This Episode:

[00:00:00] Introduction.

[00:00:20] Cate Brinch introduces Dan Fitzgerald and the origins of Heartbreak Running Company.

[00:01:52] Dan shares his background, meeting business partner Justin at Boston College, and the decision to start the company together.

[00:03:34] How the surf industry and Quiksilver influenced Heartbreak’s culture and business philosophy.

[00:07:20] Opening the first store in Boston’s South End and becoming part of the neighborhood community.

[00:10:56] The evolution from South End Athletic Company to the Heartbreak Running brand.

[00:11:29] The history behind Heartbreak Hill and why it became the company’s name.

[00:12:54] Building a brand around resilience, failure, and the emotional side of athletics.

[00:14:09] Designing the Heartbreak logo and creating a brand that represents Boston beyond stereotypes.

[00:16:28] The company's expansion from Boston to Cambridge, Chicago, and Santa Monica, including lessons from the pandemic.

[00:17:47] Opening the Santa Monica store and the full-circle connection to Dan’s Quiksilver career.

[00:21:49] Why authenticity, consistency, and perseverance matter more than elaborate business strategies.

[00:23:05] Dan and Cate discuss luck, grit, business partnerships, and learning from mistakes.

[00:26:15] Favorite brands, Heartbreak’s bestselling products, and seeing the brand worn around the world.

[00:28:05] Memories of the South End community, run club culture, and neighborhood gathering places.

[00:30:13] Meeting his wife, Rebecca, and lessons about leadership, community, and earning respect.

[00:33:04] Dan’s biggest takeaway after 17 years in business and where to find Heartbreak Running online.

Links:

Dan Fitzgerald on LinkedIn: https://www.linkedin.com/in/dan-fitzgerald-306180298

Heartbreak Hill Running Company: https://heartbreak.run