Jason Benn
Jason Benn

Jason Benn

Welcome! I’m Jason Benn, and these days I’m mainly known as the founder of the Neighborhood (and now City Campus, and City Campus Real Estate), a one-square mile community of communities in SF that aims to recapture the vibes of a university campus, but for all generations. The Neighborhood is part of a local movement composed of coliving (one big rented house), cohousing (multiple adjacent owned houses), third spaces (community centers), and good vibes (I bump into friends once every 40 minutes around Alamo Square, Lower Haight, NoPa, Duboce, and Hayes Valley).

When I co-founded the Archive coliving house in 2017, I didn’t suspect that it would have such an impact on me. Living around people that inspire me destroyed my limiting beliefs even as we all grew more connected. But I also knew I’d never be able to raise a family in a coliving house. So, after the Archive, I began to experiment. As I stumbled upon little successes and educational failures, my aspirations have grown. I share those lessons here in the hopes that others will also be inspired to live closer to their friends!

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Here are my past updates:

Apr 24 🧬#12 Launching City Campus. Doubling down on the success of The Commons.

Feb 24 🛠️#11: the Village Retreat, Treehouse, and Cohousing. Gathering families.

Jul 23 🤖#10: The Unconference to Community Pipeline. Unconf #2 iterates on the format.

Mar 23 💘#9: The Neighborhood’s First Unconference. “Scenius” can come from events?

Nov 22 🤯 #8: The Summer of Spaces. Other organizations start planting here, too.

May 22 🎉#7: Launching The Commons. Helping start a third space in Hayes Valley.

Apr 22 🤓#6: Becoming Hyper-Local Real Estate Guy. Folks are starting to move!

Feb 22 🧐 #5: Derisking the Neighborhood and choosing a location. Researching locations.

Nov 21 🎃#4: A glimmer of product-market fit. A neighborhood might be the right format…

Sep 21 🕸️#3: Writing about a Web of Questions. What questions could I explore for years?

Aug 21 👟#2: NYC coliving would look very different than SF. Visiting and learning from NYC.

Jul 21 🌱#1: A new understanding of community. Starting my exploration.

Selected writing about community. My favorite posts, essays, and tweets about community that are representative of my thinking at the time:

Dec 23 🧬 Announcing our next unconference: HammingBio Symposium

Jul 23 🛠 The unconference toolbox

Apr 23 🧭Choosing a career path when you’re uncertain

Mar 23 💘Califlorence Climate: reflections and takeaways

Nov 22 🗺 Let’s build Flock to increase serendipity with your best friends

Nov 22 🤗 Retreats that turn strangers into squads do these 5 things

Nov 22 🧭 You’re invited to Explorers Club

Feb 22 🥇 Choosing the location of the Neighborhood

Dec 21 😍 The dimensions of scenius, and how we might reproduce that culture

Jul 21 🌆 Surprising differences between SF and NYC

Jun 21 😤 I quit my job...!

Mar 21 👵🏼 Different kinds of meaning gained from community

Dec 20 🔥 Elliott Jin interviewed me about cohousing: the 18min summary

Sep 20 🍳 Breakouts: how to divide labor fairly in coliving houses

Jun 20 🗺 A mindmap of my community beliefs

Sep 18 😫Participation at the Archive, and how to support disengaged housemates

Oct 18 🤯 Megyn Kelly interviews us about coliving on live, national TV

Aug 18 👩🏼‍🎤Interview with Andrea Martinez from the Embassy house in SF


My engineering career, in reverse order

Before this expedition into community, I was a Machine Learning Researcher at Generally Intelligent, where I helped build a self-supervised system that solves infant cognitive development milestones from object permanence until we reach human-level general intelligence. I also designed and prototyped a collective intelligence tool for AI research called Exobrain.

Before that I was the Founding Machine Learning Engineer at Sourceress, where I trained the first models, built the model pipeline, hired and trained a data labeling team based on case studies I conducted of successful ML organizations, and then automated the entire process. These ML models worked well and we eventually sold our code, models, and data to a handful of other organizations.

Prior to that I was a software engineer at the nomadic university startup Minerva, where I implemented the grading system and the classroom product, which is essentially a pedagogically-inclined Zoom.

And my first engineering job was at Clinkle, where I became the lead web developer within a year of learning how to code. But we don't talk about Clinkle. Just kidding. It was wild.

During these 8 years I alternated between full-time and part-time teaching myself how to code. I actually started my career in a dead-end finance job with no technical skills!

“Jason Benn’s transformation is nothing short of astonishing.” — Cal Newport, Deep Work (p8-11)

In 2013, at 23 and motivated by a quarter-life crisis, I explained to my parents via PowerPoint that I thought it was a good idea to read programming textbooks in the basement until I got a job as a programmer. Fortunately, it only took six weeks of studying before I discovered Dev Bootcamp, which 3x’d the rate of my progress. Seven months later, I had my first job. This was the year I discovered my agency.

Ever since, I’ve found it quite enjoyable to learn. Between 2013 and 2021 I averaged 5-10 hours of studying per week. I designed and then completed curriculums in programming (1 year), computer science (3 years), machine learning engineering (3 years), and AI research (2 years). My guiding principle was to simply maximize my usefulness, so that I could negotiate for working conditions that are most linked to career satisfaction: autonomy, mastery, and purpose.

I’m glad I never saw this doc back when I was getting started, though. It would’ve scared the crap out of me.

Another direction that has me excited is building an Ivan Illich-style “learning web” around AI tutors. Studies have shown that the average tutored student performs better than 98 percent of non-tutored students. When you look at historical geniuses, you can’t help but notice that most were essentially raised by their tutors. Incredibly, and just in the last few years, large language models have become powerful enough to be this for everyone.

I think edtech way underrates the importance of colocating students, and that community structures like the Neighborhood will have an important role to play. Education is a function of motivation, and motivation is often social!

Everything else

Contact. I think the future of making friends is online first, offline later. That's why this page exists! In case it wasn’t clear earlier, I'm based in San Francisco.

Inner work. San Francisco has a classic techie → hippie character arc and maybe I’m not as unique as I thought. I’m more into emotional fluidity than meditation, and I know it’s working when I feel a greater capacity for love.

Tools for thought. Genius is overrated. Thinking quickly, which is a talent, is trumped by thinking well, which is a skill.

I’m also fascinated by worldview building. How might one incrementally build up an original body of thought? I can't stand that I don't remember 99% of what I read.

Drumming. I played so much Rock Band in college that I was left with no choice but to become a real drummer. I peaked when I recorded a rock album with my dad called The Basement Sessions.

🤘 Here's a rock song.

😴 Here's a chill song.

Books. My favorite spot to read is in my 6-person hammock, which I usually set up in Buena Vista Park. I love to organize book clubs and reading retreats.

Art. I was obsessed with drawing and painting dinosaurs as a kid. I still dabble.

🐿 Here's a Google Photos album.

Productivity. They say that gentlemen don't give advice. As everyone knows, I'm no gentleman. Here are some strategies that have made me more effective.

Personal experimentation. My body is a temple testbed. One month I drank nothing but Soylent.

Legacy. Tina Kim and I unofficially broke the Guinness World Record in the undeniably prestigious & competitive "Most lemons caught blindfolded in 30 seconds", with 35.

Thanks for reading! The best way to connect is to DM me on 🐦 Twitter.

Due to a quirk in how Notion lays out links, this toggle is simply a place to “hide” pages that I mentioned above. There’s nothing new in here.

🌱A roundup of social media posts about community

🔰Tools for thought social media posts

📚How I went from finance → AI🧭Choosing a career path when you’re uncertain