In this episode of How We Connected, hosts Aaron Hurst and Charlotte Massey discuss the importance of building connections and the role of repetition in forming strong friendships. They welcome guest Darilys, a community builder who shares her experiences and challenges in creating social groups in Boston. Darilys touches on the cultural differences between Puerto Rico and mainland U.S. and the impact of hostility towards immigrants on her Latino-focused group. She also discusses the strategies she employs to foster connections, including hosting coffee socials and leveraging technology platforms.
00:00 Introduction: The Mission
14:59 Welcome Darilys
16:10 Origin Story: Moving to Boston
20:48 Starting Friends Beyond Boston
23:20 Platform Changes & Moving to Heylo
27:03 Coffee Socials
30:49 Cultural Differences: Puerto Rico vs Boston
35:16 Advice for Community Builders
38:17 Reflection
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How We Connected explores the conversations that power communities across the United States. Aaron Hurst and Charlotte Massey share what they’re building at the US Chamber of Connection and speak with leaders whose work strengthens local connection. Episodes offer human stories, practical insights, and ideas you can use in your own community.
Aaron Hurst, Co-Founder of the US Chamber of Connection, is a longtime entrepreneur focused on purpose and community. He founded Imperative and the Taproot Foundation and wrote The Purpose Economy.
Charlotte Massey, Co-Founder of the US Chamber of Connection, leads community programs nationally. A Forbes 30 Under 30 honoree and former organizer and founder, she works at the intersection of civic life and entrepreneurship.
Connect with Us
Raices Latinas / Friends Beyond Boston
raiceslatinas.walthamsocial.com
Darilys, Founder, Raices Latinas/Friends Beyond Boston
Darilys is the Founder of Raíces Latinas and Friends Beyond Boston. A Puerto Rican community leader based in Boston, she focuses on building belonging and cultural pride. Her work centers Latino voices while creating bridges across communities. Through events, storytelling, and partnerships, she strengthens civic connection and mutual support.
Heylo
Heylo is a community-management platform built for real-world groups of every kind, giving leaders a clean, branded home base to run events, manage members, communicate clearly, and handle payments without friction. It brings scheduling, RSVPs, waivers, announcements, topic-based chats, and membership tools into one place so clubs, teams, and interest groups can stay organized and connected without the noise of traditional social platforms.
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