This is cross-posted from my “monthly” newsletter that I diligently update every quarter. I’m the founder of the Neighborhood, a one-square mile multigenerational campus made of coliving houses, coparenting villages, third spaces, and quarterly unconferences in the heart of SF. We’re now a 501c3! Check out past updates at jasonbenn.com.

In my last update, I described our first unconference. Well, three months later, we (myself and the dependable Kay Sorin) have just wrapped up our second! It was themed around aligned AGI and 100 people came, including some Very Important ones.¹

The reason I'm so into hosting unconferences these days is because it seems that a well-structured unconference can create enough momentum to materialize an inspiring new community in just 3-6 months. By the numbers:

1. Califlorence Climate had 45 applicants that were at least 40% open to coliving. That’s produced a group that has been steadily meeting, bonding, and recruiting every week since April, and we’re on track to fill our 10BR house (14BR next year) on the Panhandle by September 1st. I’m super proud of this group. I think they’re at least as warm and inspiring as the Archive was when we started.
2. Califlorence: Aligned AGI had 56 applicants that were at least 40% open to coliving. A group is just now starting to assemble. Their new 12BR (18BR next year) is scheduled to open October 1st (although it might be delayed because our renovation plans might get Discretionary Reviewed due to an ornery neighbor — welcome to real estate in San Francisco).

To me, this is a miraculous discovery. Last year I was struggling to piece together any community with my semi-monthly public meetups attended mostly by people that didn’t know each other, and now we’re materializing top-tier houses with arbitrary themes once per quarter.

What was cool about our unconference

The main constructive feedback we got last time was that 3 straight days of indoor large group conversations, while stimulating, leaves people feeling absolutely destroyed. I suspected that something should change when I had to wake up Christina Jenq for her own session. We ended up swapping another session out for Nap Time.

So we mixed up the format this time. The idea was to break people up into small groups for every meal and dispatch those groups to local cafes and restaurants within walking distance. Advantages:

1. People are going on 5-20 minute walks with each other, in the sunshine, 4-6x/day
2. It not-so-subtly gave people a taste of the Neighborhood lifestyle
3. It massively simplified logistical complexity during the event. Last time, most organizer headaches were from coordinating food, staff, and chefs. By paying a one-time, up-front programming cost, we were able to outsource 75% of our meals
4. As a result, we were able to reduce prices from $400 to $200
5. It allows us to start building relationships with local businesses like Palmyra, The Mill, Dumpling House, Arbor, Lady Falcon, etc
6. Most importantly, attendees would get uninterrupted, high-quality conversations in quiet settings throughout the weekend, making for a much more humane pace and allowing people to build real relationships with at least 20 other attendees each.

We could have matched people randomly and it probably still would’ve been an improvement, but I was really keen to make the groups feel like exactly the people you wanted to meet. I’m inspired by SwapCard, another conference app that allows you to request 30 minute meetings with any other attendee. The problem with SwapCard is that it only works if you take an hour to read everyone else’s bio, and we just knew that most people wouldn’t care enough.

The solution was to ask people what would make the conference great for them, and then use GPT-4 to predict who they’d want to meet.

Specifically, for every possible pair of attendees, we had a script compare Person A’s goals to Person B’s expertise (which we also gathered during onboarding), and asked GPT-4 to estimate the likelihood of them having a great conversation from 0-100%.

We also hacked together a janky website so that you could hand-request specific people, just like SwapCard. It was a big list of names, bios, and checkboxes, with the top 30% pre-selected for you. About 25% of attendees used it to tweak their matchmaking.