Community is less about the who, and more about the where and how

The times we feel full from a conversation meal

Community is less about the people and more about the structure and experience.

During Covid, I flew to Tulum to live with 19 founders at Casa Kookay. They were part of a founders’ community known as OnDeck. OnDeck, like many intentional communities, gets the “who” right, very right. They bring together people who share similar goals and ambitions in a carefully designed container. With this group, I felt I’d finally found my kind—people imbued with high risk tolerance, agency, and ambition. I was no longer weird; I felt I could take on the world.

Yet, it wasn’t the intellectual conversations that bonded us; it was making dumplings together, diving in the cenotes, and sharing uncertainties and struggles in a large house during a storm. In those shared experiences, I saw them in dimensions beyond their founder identities.

I have a theory about the conversation meal: conversations are like a multi-course meal.

🍢 Sample: surface-level conversations, small talk, what you do for work

🍤 Appetizer: more fun, engaging, sometimes intellectual conversations, often around shared interests, activities, or goals

🥘 Main course: deeper conversations, what’s top of mind, where we feel seen

The sample is equivalent to surface-level conversations, often transactional, spoken without much thought or deliberation. When we know little about each other or are just filling space with words, we default to the least common denominator: what you do for work, where do you live, how’s the weather. Most networking mixers, panels, and conferences live in this realm. Like food samples at a farmer’s market, we get a taste, but rarely leave satisfied.

Shared interest groups pave the way for appetizer-level conversations. A common activity or passion dissolves the small talk and skips straight into something we care about. Communities like OnDeck sit in this realm. These aligned spaces spark some of the most energizing, intellectual conversations—rich in learning and growth.

But appetizers, like their function in a meal, are meant to stimulate the appetite. Appetizer conversations signal that someone is interesting, cool, or accomplished. They leave us wanting more.

Main course conversations are those with depth. They’re about getting to know someone beyond shared interests and into other dimensions that make them whole. They’re about sharing what’s truly on your mind and providing an honest response to “how are you” beyond “good.” They’re not just exchanges of intellect and achievement, but of feeling, emotion, and vulnerability.

Once, I sat with another founder friend at a Starbucks in Tulum. Despite the shiny things he posted on Twitter—product launches, witty insights—he said, “I still haven’t tried to build something of my own, to raise a lot of money and fail. I’m not afraid of failing, but I’m afraid of never trying my hardest.” I haven’t spoken to him much since, but somehow, because of that conversation, when I see him on Twitter these days, I see something a bit more. Instead of perfection, I see times of self-doubt. Instead of bragging, I sense kindness and a desire to help.

In conversations like the one in Tulum, I felt full.

Inspired by Maslow’s pyramid, I think we’re truly fulfilled when we engage in main course conversations (icon credit: Tatyana)

The “where” and “how” boil down to a profound shared experience. The environment primes us for deeper conversation and connection. I don’t believe traveling to a different country is a prerequisite for breeding these connections. It can be as simple as soft music, conversation prompts, or a safe space that allows for main course conversations to blossom.

Community is defined by commonality, but I'm more excited about the differences: different industries, things they care about, and how they spend time. In the founder example, I’d love to know: What other verticals of life matter to you outside of building a company? Instead of talking about fundraising, want to make some dumplings?

A friend described the “sweatpants test”. To really know someone, we need to see them not when they’re polished, but when they’re relaxed: brushing their teeth, lounging in sweats, and babbling about relationships.

Once I hosted an “I Am Here Day” (inspired by Priya Parker’s Art of Gathering): a ten-hour hangout without technology with eight curated friends–some of whom I’d just met for ten minutes but thought energetically aligned. After a fully present day adventuring around Pac Heights, Golden Gate Park, and Chestnut Street, the main course conversation naturally unfolded. We ended up in a private room at a bar, savoring our “main course”; the bar owner sensed our energy and asked to join us for the next time.

These days, as I index the “where” and “how”, I’m hosting tea conversations in New York. Here, we sit on the floor with warm drinks in a cozy environment that invites us to relax, with conversation coasters prompting main course conversations. We talked about in what ways we are our biggest enemy, who we love and what we’re doing about it, and what’s truly top of mind. I love collaborating with other communities that get the “who” right and bringing them into a new context—so we can all feel full, together.

And maybe dessert is the true friendship that follows.

In a meal, dessert provides a sense of completion and satisfaction. A French friend said, “It’s obscure to end a meal with the main. We always eat something sweet at restaurants and home. Even if it’s simple, like yogurt or fruit.” In a conversation meal, ​​dessert is when community turns into friendship—when the shared thread stretches beyond the shared interest, and when some of these connections stay in our lives.

It’s that taste of sweetness that lingers.

Thank you friends from Write of Passage, Essay Club, and CansaFis’s gyms for the brainstorming and edits: John S., Becky (

Becky Isjwara

), Michael Dean (

Michael Dean

), (Leo Ariel

Leo Ariel

), Lily (

Lily

), and Mak Rahman.

Thank you, Chris, for inspiring this post with this quote:

“Tea Connections taught me that my whole life I've been having "appetizer" level conversations when I could be having "main course" conversations that are much more nourishing and hearty.”