Jason Benn
Jason Benn

Jason Benn

Welcome! I’m a self-taught ML engineer now coordinating the Neighborhood: a multigenerational campus of 200+ friendly, ambitious nerds live within a square mile in central San Francisco. It’d be as homey as a small town and as lively as a college campus, while still having all the advantages of being in the middle of the big city.

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. Now that the pandemic is causing so many people to reevaluate how and where they live, we’ve decided it’s time to build something with 10x the scale and 10x the longevity.

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Here are my past updates:

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

Jun 21 😤 I quit my job...!


My engineering career, in reverse order

Before this expedition into community research, 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.

I don’t know where my career will go after the Neighborhood is thriving even without my full-time attention. The opportunities seem to be multiplying exponentially with time, though. One 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.

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