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

In this episode of South End Stoop Sessions, Cate Brinch sits down with sisters Megan Flynn and Mariah Flynn Riordan, founders of M Flynn Jewelry, to discuss how the jewelry industry has transformed over the last two decades. They examine the dramatic rise in gold prices, the emergence of lab-grown diamonds, and how those shifts have impacted both consumers and independent jewelers. Megan and Mariah share how their custom jewelry business has evolved, their approach to curating designers from around the world, and why storytelling remains at the heart of every piece they create. They also reflect on building a business in Boston’s South End, supporting local community events, and helping customers celebrate life’s biggest milestones through jewelry.

Key Points From This Episode:

[00:00:00] Introduction to the episode.

[00:01:15] Megan and Mariah reflect on more than 20 years in the jewelry business and the evolution of M Flynn Jewelry.

[00:01:55] The dramatic rise in gold prices and the challenges it has created for jewelers and customers.

[00:03:31] Growth of M Flynn’s custom jewelry business and reimagining existing jewelry through redesign and recycling gold.

[00:04:38] The arrival of lab-grown diamonds and how they have changed the jewelry industry.

[00:06:40] Differences between natural and lab-grown diamonds, including resale value and long-term investment considerations.

[00:08:24] Ethical sourcing misconceptions and the impact of natural diamond industries on local communities.

[00:09:18] Why M Flynn chose to focus exclusively on natural diamonds and quality craftsmanship.

[00:10:52] The appeal of unique diamonds and changing consumer preferences away from perfection.

[00:12:39] The market for colored gemstones and the future role of lab-grown stones.

[00:13:32] Antique diamonds, their distinctive characteristics, and their growing popularity.

[00:15:35] Building a curated collection of designers and expanding beyond in-house jewelry production.

[00:17:31] Attending major jewelry trade shows to discover new designers, gemstones, and trends.

[00:18:59] Longstanding designer partnerships, including Jade Trau and Melissa Kaye.

[00:20:49] M Flynn’s annual Nantucket pop-up event and community-focused experiences.

[00:21:05] The origins of the South End Stroll and M Flynn’s involvement in building neighborhood connections.

[00:21:45] Combining custom jewelry with carefully selected designer collections to create a unique retail experience.

[00:22:41] The role jewelry plays in marking important life moments and family milestones.

[00:24:24] Creating an approachable, welcoming jewelry store experience without pressure or intimidation.

[00:25:56] Rapid-fire questions, including favorite pieces, neighborhood spots, and memorable product experiments.

[00:27:35] South End business recommendations and community collaborations.

[00:28:19] Where to find M Flynn Jewelry online and on social media.

Links:

Megan Flynn on LinkedIn: https://www.linkedin.com/in/m-flynn

M Flynn Jewelry: https://www.mflynnjewelry.com

In this episode of South End Stoop Sessions, Cate Brinch sits down with Jon Olinto, co-founder of B.Good and founder of One Mighty Mill. Jon shares his journey from building a fast-casual restaurant brand to addressing a major issue in the American food system: flour. He explains how industrial processing strips nutrients from wheat and how One Mighty Mill is working to bring them back through stone milling organic grains. The conversation covers the early days of testing recipes in the South End, scaling production nationwide, and partnering with schools and major retailers. Jon also reflects on entrepreneurship, emphasizing the importance of solving real problems.

Key Points From This Episode:

[00:00:20] Introduction to Jon Olinto and his South End roots

[00:01:47] Origins of One Mighty Mill and early R&D in the South End

[00:03:13] The problem with processed flour and its impact on nutrition

[00:05:28] Vision to build a national brand and transform the food system

[00:06:02] Founding story of Be Good and early lessons in food sourcing

[00:08:44] Realization that bread and flour were overlooked ingredients

[00:10:08] Identifying flour as a major gap in consumer awareness

[00:11:11] Sourcing organic wheat and discovering stone milling

[00:13:28] Building proof of concept and early experimentation process

[00:14:18] Using Cathedral High School kitchen for product development

[00:16:07] Launching the business and early customer feedback loop

[00:17:31] First major partnerships with Boston Public Schools and retailers

[00:18:32] Expansion into Whole Foods and national distribution

[00:19:46] Challenges of scaling a fresh, non-shelf-stable product

[00:20:50] Building regional mills to support national growth

[00:21:41] Misconceptions around gluten and processed food systems

[00:23:09] Launching new products and working with major partners like Costco

[00:25:27] Favorite South End spots and community ties

[00:26:20] Advice for entrepreneurs: solve a real customer problem

[00:27:27] Community impact through school partnerships and employee ownership

[00:29:47] Full-circle connection from South End beginnings to national growth

Links:

Jon Olinto on Linkedin: https://www.linkedin.com/in/jonolinto

One Mighty Mill: https://www.onemightymill.com/