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May 29, 2025 71 mins

The first time a kid tried to be friends with Trip O’Connell, Trip kicked him in the head.

“I was not a friendly kid,” Trip recalls.

It’s a surprising backstory for a community leader celebrated for cultivating caring and connection. After serving for six years in the United States Air Force as a Tactical Air Control Party/Joint Terminal Attack Controller, today, Trip is Senior Program Manager for +More Perfect Union, a “next-generation civic and service organization” that “brings people together in real life to bridge divides through service projects, meaningful conversationals, and civic engagement.”

He’s also a former gym owner, both in and outside the CrossFit space.

Listen in as Trip joins Infinitely Scalable podcast co-hosts Tony Ronchi, Cary Hair, and Andrew Charlesworth for a discussion on the intersections of success, community, and connection.

“I think that ultimately, in the end, it is the community that matters,” Trip says. “If you are able to build that community for longevity … you're really going to benefit the people that come to your gym, and you'll benefit the community more broadly because of the benefits that the people from the gym grow with and what they take out when they leave the box.”

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CHAPTERS

0:00 Intro

10:06 Connection: from protective mechanism to authentic relationship.

16:38 A trip down Trip memory lane: Gym ownership in and outside the CrossFit space.

25:07 Success, making money, and not being an asshat.

35:20 Connection, business, and what matters most.

48:27 Missing identity, the hunger for a tribe, and the tough conversations that build bonds.

53:39 Churches, CrossFit gyms, and … Joe Rogan?

1:02:10 Communication, curiosity, and getting uncomfortable.

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More Perfect Union: https://www.mpu.us/

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Infinitely Scalable Podcast: Helping entrepreneurs, creatives, and humans everywhere find freedom.

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