Entrepreneurship can be a lonely road. Between the demands of running a business and the constant push to grow, there’s often little space for real connection—the kind that goes beyond networking events and surface-level conversations. That’s exactly why Gatherings at The Annex was created by Courtney Pegan of Pegan Consulting and Sara Hine, founder of The Annex of Oakley.
This isn’t a traditional business event. There’s no sales pitch, no pressure to perform—just a table, a meal, and a space for authentic conversation. The idea is simple: bring together a small group of women entrepreneurs, create a setting where they can speak openly, and let the discussion unfold naturally.
At our most recent gathering, the atmosphere was quietly intentional—warm lighting, good food, and a group of women who showed up not just to exchange business advice but to talk about the real challenges, wins, and questions that come with this path. The Annex provided the perfect backdrop: intimate, flexible, and free from distractions.
Unlike so many events where the goal is to hand out business cards or make a quick impression, Gatherings at The Annex is about depth over breadth. It’s about sharing experiences that don’t always make it into LinkedIn posts, finding support in places you didn’t expect, and leaving with a sense that you’re not doing this alone.
The beauty of a space like The Annex is that it allows for moments like these—moments where ideas and relationships have room to grow. If you’re craving that kind of space in your own work, the question is: What kind of gathering would make a difference for you?
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