One of my defining traits is my intellectual curiosity. It expressed itself in college through taking a plethora of classes: molecular biology, computer science, the Roman Empire, the Peloponnesian War, Russian literature, multivariable calculus and countless more. However, professional specialization is the defining trait of the modern economy. We have an extraordinary quality of life because of hyper specialization. Thousands of people play a part in every product we consume. While this has allowed us to dramatically lower costs for food and consumer goods, it also makes it harder to encounter fellow generalist polymaths.

In my post college life, my curiosity expressed itself through reading 50-100 books every year. Once I could afford to, I started hosting salons based on the French 17^th & 18^th century enlightenment salons. New York was the perfect place to host them as it hosts the intellectual, artistic and financial elite. This allowed me to host salons with varying topics covering philosophy, literature, science, and geopolitics. While I might have speakers, the salons were unstructured and both intellectually rigorous and social in nature. There were 30-40 guests at most events. While I found them interesting, the quality of the conversation varied. Certain prominent guests often dominated the conversation. As there were multiple simultaneous conversations, your outcome depended on which conversation you happened to be participating in.

My approach changed after I joined Auren Hoffman and Peter Thiel’s Dialog in 2006 for what became my annual intellectual pilgrimage. Dialog uses a Jeffersonian conversation format which leads to more meaningful conversations and deeper connections. I started replicating the concept and now host regular Jeffersonian dinners in New York.

Features

1. Guest List: Typically, my dinners include 8 to 10 guests, chosen for their diverse perspectives and backgrounds. The aim is to create a group with varied experiences and viewpoints.
2. Single Conversation: Unlike traditional dinner parties where multiple conversations happen simultaneously, a Jeffersonian dinner features one continuous conversation involving all guests. This ensures that everyone is part of the same dialogue and can contribute to the discussion and allows you to go much deeper in a specific topic.
3. Guided Discussion: I typically moderate the conversation around the central theme or question for the evening that I share with the guests by email ahead of time. This question is meant to be open-ended and thought-provoking, designed to elicit deep and meaningful responses.
4. Equal Participation: Guests are encouraged to participate equally. I guide the conversation to ensure that no one dominates and that quieter guests can share their thoughts.
5. Respectful Dialogue: The emphasis is on respectful and considerate dialogue. Guests are encouraged to listen actively and engage thoughtfully with each other’s perspectives.
6. Limited Interruptions: Interruptions are minimized to allow for uninterrupted sharing of ideas. Guests take turns speaking.
7. Personal Stories and Insights: Guests are encouraged to share personal stories, experiences, and insights related to the central theme. This personal approach helps to foster a deeper understanding and connection among participants.
8. Round Table: You can obviously use a traditional rectangular table, but you end up with more distance between the participants. I intentionally use a small round table to facilitate more intimate conversation.

Timeliness

I typically tell people to show up at 7 pm with the dinner starting at 730 pm. The first 30 minutes are unstructured. Once we sit down, we transition over to a single conversation starting with brief introductions. I give a 30-minute buffer given that subway and traffic conditions in New York may vary. However, anyone arriving after the structured conversation starts at 730 pm is not allowed in.

At 930 pm, after two hours of conversation, I let people know that they are allowed to leave if they have obligations, but that people are welcome to stay for as long as they want.

Rules

• Group Discussion: The magic of a dialoging dinner is the conversation and ideas generated by our collective minds. Only one group conversation is allowed at the dinner table. Side conversations are not allowed.
• Attribution: Everything about the conversation is off the record and not for attribution.  And by “everything” I mean who participates, what was discussed, the food we ate, what the weather was like…everything.
• Attire: Dress is casual.  Jeans are encouraged.  Ties are discouraged.  
• Adialoging dinner is a problem-solving session. It is not a debating session.   We’re not coming together to see who can score more points in an argument. We’re here to do deep problem solving. We’re all on the same team and we’re looking to solve the problems together.
• Take preparation seriously.
• Do not check your cell phone.  Turn off mobile phone rings and vibrations.
• If you are ever speaking for more than a minute at once, it better be good.  If you speak for more than two minutes at a time, it should be mind-expanding.  If you speak for more than four minutes at one time, you won’t get invited back.  Try to listen and engage: “Judge a man by his questions rather than his answers.” -Voltaire

Topics

Jeffersonian dinners can be used to go deep in any topic. Noah Friedman and Michael Loeb admirably use their Uncharted Dinner Series in New York to focus on the plight of the entrepreneur. In line with my intellectual curiosity, I typically alternate between three different types of dinner topics.

1. Open Ended:

Some of the most interesting and eye-opening sessions I had was when I asked the participants to pick one of the following topics.

1. Dialoging
   Take 4 minutes to present something interesting and teach the group about something.  We then discuss each presentation. Expectation: you need to prepare a 4-minute talk.  Think beforehand about what you want to present and discuss. It should be eye-opening, very interesting, and not overtly partisan.

1. That’s Bullsh*t
   Discuss over-hyped arguments, theories, and predictions currently dominating in politics, science and technology discussions. Topics may include American declinism, Chinese ascendancy, yoga, 3D printing, college-via-internet, Bitcoin, Snapchat, kale, drones, paleo diet, meditation, electric cars, and more. Give a 4-minute explanation of what you think is bullshit and why. Rebuttals encouraged. Note: Arguments should be provocative/controversial but not overtly political or partisan.

3. That Which Cannot Be Said
   What is the most controversial or heretical idea, belief, or theory you have? Every participant gets four minutes to present. This session is about truth-seeking, not arguing for argument’s sake. Following presentation of all the opinions, participants will vote thumbs up or thumbs down on each opinion in sequence. The goal is to present an opinion that as few people agree with you on as possible, but not zero. Ideas should be provocative or contrarian but not overtly partisan or political.

These dinners are those where you learn the most and are inevitably surprised by what others present. However, they are shallower as each guests covers a different topic.

2. Personal:

Dinners with personal questions end up leading to the deepest connections between guests. The questions are designed such that each guest must share detailed stories giving you a glimpse of their history and psyche. With everything being off the record, most people show amazing vulnerability and earnestness.

Here are the questions I recently used for such a dinner.

• If you were to write a memoir about a single 72-hour period of your life, which three days would you pick?
• What event in your life felt big at the time but didn’t shape your path how you thought it would? What in your current life could prove the same?
• What have you fought for more than anything else in your life? Has the fight been worth it?
• What vice do you consider a virtue?
• What’s a view that you hold that you can’t defend?

Note that we cover all 5 questions during one dinner.

3. Intellectual:

The most common dialoging dinner I organize is around a topic of interest to me at the time. Here are some of the topics I covered over the years.

• Techno-optimism & pessimism.
• Reinventing democracy for the 21^st century.
• Religion in 2100.
• The ethics and morality of torture.
• The future of war.
• Power.

Note that the topic above is the general theme for the evening. For each I typically prepare 3-5 more detailed questions that I ask the participants to ponder.

For instance, here are the sub-questions for the techno-optimism conversation:

• In what surprising way are you a short-term techno-pessimist, but a long-term techno optimist, and vice versa?
• Which industry is least prepared for the impacts of AI, but surprisingly well positioned to take advantage of it? 
• What will be the non-obvious critical inflection points in science and technology in the next year? Ten years?
• What ethical questions related to emerging technologies do you find most impossible to reconcile?

Aftermath

There are no specific objectives of dialoging dinners other than to foster rigorous intellectual discourse. You could accuse them of being merely intellectual masturbation. Honestly even if nothing came of them, other than improving each other’s knowledge, I would deem them a success.

I have learned so much from them over the years. We often came away with fundamentally contrarian conclusions. For instance, during the dinner on reinventing democracy for the 21^st century, we ultimately concluded that for all its faults the American constitutional republic was the best political system. Given that none of us started with that position, the path and leaps it took to get there were fascinating.

Regardless, I feel that there is magic to these gatherings that extends beyond mere intellectual stimulation. Serendipitous meetings at various Jeffersonian salons have led to business deals, policy changes, and even marriages. I feel that they will play a role in shaping the cultural and intellectual landscape of the 21^st century and contribute to the spread of new ideas and the promotion of critical thinking.

You now have the toolkit to host your own and bring forth new extraordinary ideas!