This past summer, 5 to 9 Society moved from idea to reality. Toronto set the tone, Montreal brought its sharp curiosity, and New York added its unmistakable velocity. Across a handful of dinners and dozens of conversations, a pattern started to emerge in the quiet moments I watched founders, operators, and investors connect in ways that felt both rare and strangely inevitable.
These are the five lessons I keep returning to.
1. Be discerning about who’s in the room
If there is one job I will still do ten years from now it’s vetting every single member who walks into 5 to 9.
Our values aren’t abstract or performative. They’re our operating system. They articulate who belongs and, more importantly, who does not. When you’re building something intentionally small, values become the boundary. They’re not just a list on the website, they’re the filter that shapes the entire experience.
I’ve learned that discernment isn’t about snobbery, it’s about alignment. It’s about putting people in rooms where their ambition, generosity, and curiosity don’t feel out of place. When the fit is right, people relax. They open up and offer their best thinking. You can actually feel the energy shift.
What surprised me is how much members value the curation itself. They sense when a room is built with intention and values alignment, and they treat each other accordingly.
2. Host earlier, not later (5 to 9 is the sweet spot)
One of the simplest but most important discoveries: early dinners work better for high-scope people.
A 6–10 pm event sounds good on paper, but the reality is that many of us are juggling leadership roles, families, commutes, and the sheer cognitive load of decision-making all day long. People naturally start slipping out at 9 pm anyway, which happens to be exactly when our name becomes a funny little coincidence.
The earlier window creates a different kind of presence. People show up refreshed, the conversation lifts faster, and the night ends at the right moment, not when everyone is too tired to offer their best self. It’s a small structural decision that completely changes the energy in the room.
3. Time is infinite and you feel it more as a Founder
You can earn more money, raise more capital, or scale more operations. But sadly, time doesn’t work that way.
Since launching, I’ve had countless people ask to “pick my brain,” often kindly, often with good intentions. But the truth is, I don’t have the luxury of extra hours for virtual coffees. That’s the cost of building something yourself. You become ruthless with your time because you must be.
What I’ve learned is that the most valuable thing I can give is not open-ended access; it’s a thoughtfully curated community where the right conversations happen between the right people. That’s the real leverage.
4. A community becomes real when people invest in one other, without being asked
I wanted 5 to 9 to be a network where leaders genuinely supported one another, where help flowed horizontally, not top-down. And now I see it happening: members introducing each other to their networks, sending referrals, giving recommendations, offering insight, making the kinds of introductions you cannot buy.
In a world that feels colder and more transactional every year, there’s something remarkable about watching people lean in because they want to, not because they’re obligated to. That generosity is the heart of 5 to 9. It’s the part I’m proudest of.
5. Many communities fail because they dilute. We’re not doing that
This is the piece that still stops me in my tracks.
I’ve spoken to so many members who have left other communities, or who are in the process of leaving, and the story is always the same. They accept everyone, then it became transactional. Then the room changed and the energy shifted. Suddenly, it didn’t feel special anymore.
Once a community dilutes, it’s almost impossible to rebuild the original spirit. That’s why our guardrails and values matter. That’s why I take vetting so seriously. Scarcity isn’t a marketing tactic here, it’s what protects the integrity of the experience.
If we do this right, 5 to 9 stays meaningful and aligned. And it stays small enough to feel human, even as it grows.
What’s surprised me most is how much I’ve learned simply by watching this community take shape. Some lessons I expected, others revealed themselves only in the flow of real conversations and real rooms. As we step into 2026, I know there will be more to observe, more to refine, and more to protect. Building 5 to 9 is teaching me as much as it’s connecting the growing Society. I’m looking forward to the next chapter with a deeper sense of clarity and curiosity.
