Behind the Scenes of a Thriving Membership with Entreprenista’s Stephanie Cartin

·39 min·3 clips

Stephanie Cartin warns that if you don't like people, you shouldn't build a membership community.

The episode begins with Stephanie Cartin emphasizing that memberships are a long-term commitment, not a quick win, with compound effects often seen after 18 months to three years. Host Julie Solomon introduces Stephanie, noting her previous appearances and the evolution of Entreprenista. Stephanie recounts the origin story: she and co-founder Courtney started Socialfly, a social media agency, in 2012 after quitting corporate jobs, and launched the Entreprenista podcast in 2018 as a side project. During the pandemic, they pivoted to focus on building the Entreprenista League community, which now serves as a full media company. Stephanie discusses the challenges of membership growth, stressing that community leaders must genuinely like people and be actively involved. She shares tips on using platforms like Circle for technology and listening to member feedback to adapt offerings. The conversation covers the community's structure, with 50% service-based and 50% product-based businesses among its 2,500 members. Stephanie highlights networking events, virtual meetups, and local member programs that foster connections. She illustrates the community's impact with a story about Gwen Whiting, founder of The Laundress, who used the community to launch a new business after a $100 million exit. The episode also details the Entreprenista 100 awards program, created to recognize women-founded businesses at various revenue stages. Stephanie announces upcoming initiatives, including power group programs and a founders weekend retreat in 2026. Julie promotes a special link and discount code for listeners to join the community, and encourages feedback via DMs.

As heard by us

Memberships take years to compound, and the conversation treats patience as part of the strategy.

Stephanie Cartin's conversation keeps its focus on the patient, accountable work memberships require to stay relevant. It tracks how Entreprenista has grown, how launch planning and momentum shape the work, and why a membership has to behave like a living system that keeps…

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Why you'd press play

If you are building a membership, this is a long game, not a quick win, and the payoff may not show up until years in.

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