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Invite to Connect: Alexandra Freeman, Chamber of Connection
Description
Aaron Hurst and Charlotte Massey of the US Chamber of Connection discuss initiating invitations despite fear. Meanwhile, Charlotte enjoyed a trip to Minnesota for a family reunion and Aaron helped an Amazon delivery worker stuck behind a gate.
This week's guest is Seattle-based friendship and social skills coach Alexandra Friedman, who is a lifelong connector. Her work has evolved from hosting dinner parties, to 125 curated events for 2,700+ people, and into coaching on social skills and friendship. Alexandra coaches Aaron and Charlotte on capacity, group building, travel, and hosting, emphasizing a focus on invitation.
00:00 Introduction
00:29 Weekend Catch-Up
14:30 Introducing Alexandra Friedman
15:45 Childhood Roots of Connection
23:53 College, Yelp, and Career
30:09 Connection at Work and AI
33:11 Becoming a Friendship Coach
35:36 Live Mini Coaching Session
48:24 The Power of Initiation
51:06 Wrap-Up and Credits
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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
Alexandra Friedman, Connection Feast
Alex is a friendship and social skills coach and the founder of Connection Feast, a Seattle company she started in 2018 to cure her own loneliness after moving home. What began as rooftop dinner parties for strangers she'd meet at crosswalks and in Facebook groups has grown into 125 curated events and coaching that's reached more than 2,700 people. A self-described social artist, Alex helps adults build real community without giving up who they are, teaching the skills most of us were never taught: how to initiate, ask good questions, handle rejection, and turn a first hello into a lasting friendship. She works one on one, in groups, and through immersive experiences, all aimed at helping people connect more deeply with themselves and each other.
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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