It's been a busy week for Charlotte Massey and Aaron Hurst at the US Chamber of Connection. Aaron joins from a San Francisco airport while touring with board.dev, his nonprofit board effort, as the two launch Welcome Week, a week built around one idea, inviting someone to do something. Charlotte shares her own bad art from a cabin in Colorado, made just for the process.
This week's guest is Jules Costa, founder of Bad Art Club in San Francisco, where the bad is a trick to get people through the door who'd never call themselves creative. She traces the path from a decade in software to the afternoon in the Panhandle when she and a friend drew the worst portraits they could and a club was born. Jules recounts quitting tech, walking away from corporate work, and finding her footing in pro bono workshops for people in early recovery, where failing is impossible and everyone belongs.
00:00 Introduction
05:22 Welcome Week and the Culture of Inviting
10:20 How Many People Are Invite-Ready Tonight?
16:19 Welcoming Jules Costa, Bad Art Club
17:42 Leadership and the South Africa Trip
19:23 Origin of Bad Art Club
22:21 First Workshop, Going Full Time
26:07 Corporate Work and Pivoting to Nonprofit
29:10 Art in Addiction Recovery
33:20 Weekly Gatherings and the Fate Collective
38:33 Body Wisdom and Decision Making
51:33 Reflections
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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.
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Jules Costa, Bad Art Club
Jules is the founder of Bad Art Club, a San Francisco community built on the simple permission to make something terrible and enjoy every minute of it. A certified transformational facilitator and addiction recovery coach, Jules spent the better part of a decade writing software and traveling the world before she traded her tech career for a creative one. What began as two friends drawing the worst portraits they could in the Panhandle has grown into weekly workshops that draw dozens of people who'd never call themselves artists, along with public art projects, a summer retreat, and pro bono sessions for people in early recovery. Bad Art Club is fiscally sponsored by Independent Arts and Media, and Jules now spends her days designing spaces where failing is impossible and everyone belongs. Her guiding belief is that the only difference between you and an artist is the willingness to make bad art.
Bad Art Club
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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