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More members isn’t always better
Charlotte Massey and Aaron Hurst open How We Connected by reflecting on building community with the right goals, the importance of fun and resonance over sheer scale, and recent experiments in connection. This week’s interview is with Brandon DesJarlais, a world-renowned longboarder, based in Los Angeles and co-founder of Vibe Ride. He shares how a middle-school incident led him to leave a destructive friend group and how longboarding helped him face his fears. During COVID, DesJarlais shifted from competitive riding to teaching online tutorials and hosting free clinics that grew into a community of 700 active members. He describes Vibe Ride’s mission, leadership model, rituals, intentions, icebreakers, and “surprise and delight” rolling dance-party rides. A key insight? He argues that more members isn’t always better. Enjoy!
00:00 Introduction
14:22 Brandon DesJarlais: Early Life and Masking Authenticity
16:12 The Turning Point: Friends, Family and Diverging Paths
19:21 Wrestling, Skating and Facing Fears
24:33 Viral Tutorials and the Birth of Vibe Ride
27:42 What a Vibe Ride Looks Like
37:43 Sustainability, Identity and Vision for the Future
47:49 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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Brandon DesJarlais, Co-Founder, Vibe Ride
Brandon is a professional longboarder, coach, and community builder based in Venice Beach. He has competed across disciplines from downhill racing to longboard dancing, skated in 26 countries, and once stunt-doubled for Vin Diesel in xXx: Return of Xander Cage. In 2021 he founded Beyond the Board, a Los Angeles 501(c)(3) using skateboarding to build confidence and connection. Its flagship program, Vibe Ride, is the weekly sunset group ride he co-founded in Santa Monica and Venice Beach that now counts 700 active members and has been profiled by the LA Times. Brandon teaches community-building through his 4C's Framework.
Vibe Ride
www.heylo.com/blog/brandon-desjarlais-and-vibe-ride-la
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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