We recommend you start with this episode. In this preface to the second season, MassTLC CEO Tom Hopcroft tells the story of how we arrived at this season’s overarching themes, and our guests define some key terms that inform the entire season. 

In our first season, we heard conversations between leaders in Boston’s tech community, as they maneuvered through the complex realities of the COVID pandemic. But one conversation, between Anthony Williams of Akamai and Susan Hunt Stevens of WeSpire, left us questioning the very notion of Boston’s place as an incubator of talent and social change. Is Boston truly America’s most racist city? Is this just a brand problem, tied up in the city’s unwelcoming reputation, or is it true that Boston is systemically unwelcoming to people of color? And, acknowledging it as a problem, how are we, as a community, working to fight both the realities and the reputation? In season 2, On the Tech Trail, we spoke to 22 leaders in our community to directly address issues of equity, access the so-called Boston Brand Problem. 

Here are some episode highlights: 

• Anthony Williams (EVP, CHRO at Akamai Technologies) presents The Boston Brand Problem 
• Lee Pelton (President of Emerson College and the next CEO of The Boston Foundation) defines Equity and how it differs from Equality 
• Pratt Wiley (CEO of The Partnership) introduces how the pandemic disproportionately impacted communities of color 
• Stephanie Browne (VP of Talent Acquisition, Chief Diversity, Equity & Inclusion Officer at Blue Cross Blue Shield of Massachusetts) ties the Boston Brand Problem in with local “clique-ish” culture 
• Collected soundbites from some of our season’s guests, to introduce and tease the rest of the episodes, including: 
• Chris Comparato (Founder and CEO of Toast) 
• Kathleen Mitford (Chief Strategy Officer at PTC) 
• Christina Luconi (Chief People Officer at Rapid7) 
• Tim Rowe (Founder and CEO of the Cambridge Innovation Center) 
• Phyllis Barajas (Executive Director of Conexion) 
• Mike Volpe (CEO of Lola.com) 
• Sheena Collier (Founder and CEO of Boston While Black) 
• And, finally, Akamai’s Anthony Williams returns to explain how Boston’s unwelcoming reputation felt like a challenge that he could face and help resolve 

So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows, and onto the Tech Trail.