In this episode of How We Connected from the US Chamber of Connection, hosts Charlotte Massey and Aaron Hurst discuss what’s happening at the Chamber. They welcome guest Haley, a community builder in Pittsburgh, who shares her background growing up in a small town, studying sociology and psychology, and moving to Pittsburgh during the pandemic. Dog walking helped her explore the city and meet people, leading her to start a transplant meetup that grew from 14 attendees to a much larger community. She describes how her work evolved into Pittsburgh Social Health, focused on third spaces, offline meetups, and interactive programming.

Haley talks about her upcoming “Connection Expo,” a college-style club fair for adults on Pittsburgh’s South Side, featuring 80 organizations and roughly 400 RSVPs - and the challenges in sustaining community work, including time demands on volunteer leaders, keeping events accessible and low-cost, using partnerships with local business. She shares how she measures success through participant sentiment, feelings of safety and belonging, and actionable next steps.

00:00 Introduction

01:30 Weekend Catch-Up

09:11 Conference Strategy

18:54 Introducing Haley Ingersoll

20:09 Growing Up in a Small Town

21:36 Moving to Pittsburgh During the Pandemic

23:53 From 14 People to 400: Growth Story

25:14 The Connection Expo

29:20 Building Community Between Events

36:01 Economics and Sustainability

41:34 Reflection and Takeaways

46:44 Closing Thoughts

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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

Pittsburg Social Health

www.instagram.com/pghsocialhealth

Haley Ingersol, Founder, Pittsburg Social Health

Haley Ingersol is the founder of Pittsburgh Social Health, a grassroots initiative dedicated to helping people build meaningful connections in the city. With a background in social work and experience spanning human services, academia, government, start-ups, and hospitality, she brings a cross-sector lens to community building. Haley believes social connectedness is essential to overall well-being. Through social and sightseeing meetups, she creates welcoming spaces for new and returning residents to find belonging. Her work centers on equity, comprehensive wellness, and reducing social isolation. Above all, she is committed to shaping a more connected social future.

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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