This week on How We Connected hosts Charlotte Massey and Aaron Hurst reflect on Charlotte's reality-TV-competition-themed 30th birthday weekend: structured games, fondue dinner toasts, and life advice at midnight. Over at the U.S Chamber of Connection, they prepare for this week’s Seattle club fair at the Nordic Museum, the upcoming neighborhood “Best Day Ever” event in South Park, and a webinars on Main Streets and community service with Workday. The interview this week features Eric Leslie, Founder of Union Capital in Boston, who has built a relationship-driven “loyalty program” that rewards unpaid community participation with points and gift cards, hosts network nights with meals and childcare, and tracks outcomes like employment, voting, and credit-score awareness. It raises broader questions about money’s role in social connection.

00:00 Introduction

01:45 Charlotte's 30th Birthday Party

10:59 Chamber of Connection Updates

17:00 Interview: Eric Leslie from Union Capital

17:39 Eric's Origin Story

21:06 How Union Capital Works

25:22 Member Journey

33:02 Points System and What Counts

37:00 Measuring Impact and Success

42:09 Sustainable Models for Connection

47:16 Closing 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

www.chamberofconnection.org

Union Capital

unioncapital.org

Eric Leslie, Founder, Union Capital

Eric is the Founder and Lead Organizer of Union Capital, a nonprofit he launched in 2014 to transform social capital into opportunity by rewarding community engagement. Eric began his career as a community organizer with the Industrial Areas Foundation before joining Teach For America and teaching in North Philadelphia. He went on to serve as principal of KIPP Philadelphia Charter School from 2008 to 2012, then returned home to earn his MPA from the Harvard Kennedy School of Government. Under his leadership, Union Capital has grown to serve thousands of members across Boston and Springfield, awarding over $1.8 million in rewards for community involvement and hosting more than 120 Network Nights annually.

Heylo

https://www.heylo.com

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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