People often ask what actually happens inside 5 to 9.
The short answer is: conversations that would be hard to recreate anywhere else. The longer answer is that connection takes different forms, depending on the moment, the city, and what someone needs access to right now.
So instead of a schedule or a list of benefits, we thought we’d offer a glossary as a shared language for the ways members tend to find each other.
In-person Dinners
The opportunity to meet, in real life, seated around one table with a close-knit group that often becomes both peers and friends. No amount of virtual meetings compares to breaking bread together, having unhurried conversations, and leaving knowing everyone’s name. These are private dinners, hosted in intimate and often exclusive spaces, guided by Chatham House Rules so conversation can unfold freely.
Functional or Topical Roundtables
These IRL gatherings are organized around a shared function or theme, with guests invited intentionally to create a lively, thoughtful exchange. The discussion is curated, but not scripted — designed to spark debate, surface perspective, and generate ideas you’ll find yourself returning to long after the evening ends.
Virtual Fireside Chats
Each month, members are invited to a private virtual conversation with founders and leaders who have built meaningful businesses and lived through the decisions behind them. These private discussions are never shared with the public and they happen live on Zoom so our members can actually ask questions with our guest speaker. That trumps any podcast in our opinion!
Virtual Mastermind Series
Each month, we host a virtual mastermind group made of a cohort of 7-8 members. One member takes the “hot seat” to share a problem that’s keeping them up at night. The cohort group leans in, asks questions, probes ideas and shares resources, introductions, advice or support. This is better than a coaching session because you have 8 brilliant minds all focusing on the member of the month.
Consiglieres
Not all connection happens in a room or on a call. Within 5 to 9, we refer to our trusted advisors — coaches, consultants, solopreneurs, and specialists — as consiglieres, a nod to The Godfather. Each consigliere is deeply experienced in their field and carefully vetted, not only for expertise but for judgment and integrity. They are people members turn to when they need trusted counsel, thoughtful execution, or a well-placed introduction.
At a glance, these may look like formats. In practice, they’re simply different expressions of the same idea: creating rooms where where insight circulates freely and where connection has time to deepen. As the Society grows, so does our language. New ways of connecting continue to emerge, shaped by the people in the room and what the moment calls for.
That’s the throughline. Everything else is just context.
Because when people feel seen, challenged, and well-placed, connection becomes inevitable..
