Most advisors are good at filling a room. They book the private dining space, bring in a portfolio manager, offer a market update, and the clients leave saying, "Thank you for dinner.”

What most advisors are not doing is designing nights where clients leave saying, "That was one of the most meaningful conversations I have had in years.”

Tim Brown, co-founder of Somos22, has spent years building exactly that kind of experience for family offices. His Jeffersonian dinners are a 225-year-old format updated for modern families who are tired of surface-level networking and hungry for depth. At the core is a simple idea: if you change the structure of the dinner, you change the depth of the relationships that come out of it.

In this episode of Visionary Advisor, Tim sits down with host Alex Kirby to explain why this format works, what the rules are, and how any advisor can adapt it to build deeper relationships with their best clients.

Why Jeffersonian dinners work

Tim and Alex start by contrasting the standard industry event with what families actually want. Traditional conferences and client dinners focus on information: a speaker presents, slides go up, people nod, take notes, and go home. The content may be valuable, but the relationships rarely compound in any meaningful way.

Jeffersonian dinners flip that script. “The evening is really designed as a long-form, high-trust conversation,” Tim explains. The goal is not consensus, performance, or problem-solving in the sense of telling other people what to do. It is asking thoughtful questions, creating prompts that invite reflection, and letting the collective wisdom of the table emerge. For advisors, that shift alone changes the energy in the room from being a presenter to being a moderator of the most important conversation their clients will have all quarter.

The core rules of the format

Tim is clear that the format works because it has structure. Phones go away. There is no note-taking. The dinner runs for about three hours, not more. The room follows Chatham House rules, which means people are free to share openly without worrying that their comments will be attributed to them outside the room.

Within that frame, the host guides the evening. Tim likes to mix long-form and short-form questions, often organized around four or five sub-themes under one broader theme for the night. He also uses what he calls a “tip jar” at the end, a final round where everyone leans in to share a small habit, a lesson, or a piece of advice that has made a big difference in their life. The structure is invisible to most guests, but it is what keeps the conversation from splintering into side chats and keeps every voice at the table engaged.

The ultimate icebreaker for depth

One of Tim’s favorite ways to open a Jeffersonian dinner is with an unexpected icebreaker. After the basic introductions, name, where you live, and your connection to the host, he asks a question most guests have never been asked at a dinner: “What almost kept you from being here tonight?”

It sounds simple. In practice, it changes the room. People talk about work stress, family responsibilities, travel issues, health scares, and the thousand little frictions that almost made them cancel. That question gives people permission to open up and sets a tone of vulnerability without being heavy. Right out of the gate, guests lean in with just the right amount of honesty, and the conversation never quite goes back to small talk.

For advisors, it is a reminder that the quality of the first question often determines the quality of the whole evening. A better icebreaker can turn a “nice dinner” into the start of a real client community.

How to ask better questions

From there, Tim layers in what he calls long-form and short-form questions. Long-form questions are the kind that require reflection and cannot be answered in a sentence. If the theme of the night is legacy, he might ask: “Alex, if your life ended tomorrow, what story would those who know you today tell about you?” Questions like that are attached to a lot of things and invite people to share stories, not just opinions.

Tim usually spends the first sixty percent of the evening on these long-form questions, then shifts into shorter prompts for the last third. Short-form questions sound like: “What are a few patterns or routines that currently define your days?”, “What small habit made a big difference in your life?" or “What advice from your childhood has stayed with you?” The mix matters. Too many heavy questions in a row can exhaust a table. Too many light ones, and the night never goes deeper than the surface.

The bigger point for advisors is that question design is a skill. Most client events fail not because the room is wrong, but because the questions are too safe, too generic, or too focused on information. Clients remember the questions that help them see their life differently.

What the ultra-wealthy actually want to talk about

One of Tim’s early surprises when he started running these dinners was realizing how little time ultra-wealthy families wanted to spend talking about investing. “I thought everybody wanted to talk about investing,” he says. “But they do not. They wanted to talk about their kids.”

The conversations that landed hardest were about the complexities of wealth and governance, healthy marriages, and the practical questions of how to treat future sons-in-law and daughters-in-law like in- laws, not outlaws. Guests wanted to discuss how to pass values as well as assets, how to design a family bank that empowers grandchildren to feel like a first generation and to self-actualize, and how to navigate the invisible dynamics that come with multi-generational wealth.

For advisors, this is a gentle but important correction. The families you serve will always care about returns. But when you create a space where they can talk about the human side of wealth with peers who understand their world, you move from being one more information source to being a curator of the conversations they cannot have anywhere else.

A public speaker’s secret to beating nerves

Even experienced hosts get nervous before a Jeffersonian dinner. Tim is candid about his own experience. In his view, if you are not getting nervous, you are probably not taking the responsibility seriously enough. The nerves are a sign that the night matters.

He shares a public speaking trick he picked up from doing keynotes. Before he goes on stage, he always walks the front row, shakes hands, introduces himself, and learns a little about each person. When he steps up to speak, he no longer sees a faceless audience. He sees a row of allies. It feels like giving a talk to friends instead of strangers.

He applies the same idea to Jeffersonian dinners. Before the formal start, he meets as many guests as he can, often admitting how many of these he has hosted and that he still gets nervous because they matter so much to him. That honesty lowers the temperature for everyone. Advisors who worry about trying a more intentional format can borrow this directly: always meet the front row. Turn the room from an audience into a circle of people you care about, and let the nerves remind you that what you are about to do could genuinely change relationships.

The secret to compounding trust

Underneath all of this is what Tim calls connection capital. Somos22 exists to curate private trust networks for family offices. Within those networks, they define a clear set of rules, use intentional experiences like Jeffersonian dinners, and let the output be trust that compounds faster than it would on its own.

A Jeffersonian dinner is a micro version of that. It is a private trust network at a table. The rules are explicit. The experience draws on everyone’s past and future stories. People leave the room trusting each other more because the human element of their lives was invited in.

Tim’s core idea is that relationships compound the way capital does. Every well-designed dinner, every thoughtful question, and every night where clients feel truly seen adds to a balance that grows over time. Advisors who learn to host experiences like this are not just throwing events. They are building the kind of connection capital that quietly determines outcomes for families and for their own firms.

Listen to the full episode

The full conversation with Rich Ryffel is available now on Apple Podcasts, Spotify, and YouTube.

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