How We Connected

Friendship Machines: Gina Phillips, Director of Operations, Pickle at the Palms

September 9, 2026·46 min
Episode Description from the Publisher

Gina Phillips grew up in a family of introverts. When they went out to eat, everyone brought a book. As a kid, she was shy and had hearing problems. Making friends didn't come naturally. But if she made the thing happen, she had a role to play. She still calls herself your friendly neighborhood introvert. Gina won't be the life of the party, but she'll make sure it happens.That carried her from founding Seattle Startup Week to WeWork, where she led global member experience. Her training for community teams included a rule Chumstock fans will recognize: a line is an opportunity. If people are waiting in front of you, introduce them to each other.Now she's bringing all of it to Pickle at the Palms, a 20-court indoor pickleball center in Seattle's Interbay neighborhood. She's hiring for warmth. Gina's big goal for the decade isn't a full house. It's a wedding. She wants couples to meet at the Palms and she's gunning for the Best Matchmaker trophy!At the Chamber, Charlotte closes out the summer, making noises at her baby niece at the Colorado cabin. Aaron pitches a quick pickling station at Pickle at the Palms, brine, jars and all.00:00 Introduction00:29 Catching Up03:50 Meet Gina Phillips08:47 Scaling Beyond Events17:32 Gina's Origin Story21:39 Community Building at WeWork27:45 Inside Pickle at the Palms40:25 Matchmaking43:12 Reflection---The most creative artists in America right now aren’t in galleries. They’re in your neighborhood. How We Connected is a front-row seat to the social artists rebuilding human connection. Hear inspiring stories about roller skating crews, bad art clubs, jousting societies, city saunters, Georgian dinner parties, catch-playing challenges, midnight runners, and picnic societies. Hosted by Charlotte Massey and Aaron Hurst, co-founders of the US Chamber of Connection.Aaron Hurst is the co-founder of the US Chamber of Connection. He’s a longtime entrepreneur focused on purpose and community. He founded Imperative and the Taproot Foundation and wrote The Purpose Economy. Charlotte Massey is the co-founder of the US Chamber of Connection and 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 Uswww.chamberofconnection.orgGina Phillips, Director of Operations, Pickle at the PalmsGina grew up in a family of introverts who brought their books to restaurants. She learned young that if she makes the thing happen, she has a role to play. She founded Seattle Startup Week in 2013. Then came WeWork, where she rose to Global Head of Member Experience. Now she's building Pickle at the Palms, a 20-court indoor pickleball center in Seattle's Interbay neighborhood, backed by the family that owns the Seattle Storm. She plays ultimate frisbee for a team called Jazz Picnic and has her eye on the Best Matchmaker trophy. Her motto: it matters less who you know than who knows you.Learn more: pickleatthepalms.comHeylohttps://www.heylo.comHeylo 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. Hosted on Acast. See acast.com/privacy for more information.

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