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✍🏽 Welcome to Landon’s Loop: your weekly read on Chicago startups!
In this week’s newsletter #111:
- Drive Capital returns $500M to our LPs
- My visit to Fermilab where quantum meets particle physics
- What it could look like if Chicago brought AI to the masses
- A few tech events happening in Chicago this week
🔙 Highlights from Last Week
Our firm returned $500M to LPs: In a tough environment, Drive has delivered real liquidity by backing the best companies between the coasts. Great job to our team! 👇🏽

I spent a day touring the legendary Fermilab to see our country’s particle physics lab (and a few bison 🦬 ). Big thank you to Bill Pellico and Charles Tobin Thangaraj for hosting us 👇🏽

I joined my buddy George Khalife’s podcast to talk about how I’ve engineered tech communities in Chicago 👇🏽
On Saturday, we hosted Socratica at the Drive Chicago office which was a weekend AI meetup for engineers in the city 👇🏽

3 Ways Chicago Could Bring AI to the Masses

Dubai wants to become the first city to give every resident access to ChatGPT. It’s a big move and one that sends a clear message: AI is something all citizens can benefit from.
That got me thinking. If Chicago wanted to take the lead on AI, what would that look like?

Here are three ways Chicago could make AI accessible to its residents:
ChatGPT for City Data
Chicago has one of the most robust open data portals in the country, but it’s still difficult for everyday residents to access the information they need.
Imagine a Chicago-trained AI assistant accessible by text, app, or voice that could answer questions about zoning, business licenses, public meetings, sanitation schedules, transit, and more. It wouldn’t just pull from the city website. It would be trained on legislation, council transcripts, and permit documentation to provide answers in plain English.
Think: “Where’s my building permit in the pipeline?” or “Can I put a compost bin on my block?” answered instantly, 24/7.
Done right, this kind of tool could reduce 311 call volumes, increase transparency, and rebuild trust between residents and government. And for a city with deep digital divides, it would make city services more accessible than ever before.
Someone should build this.
AI Service Hubs in Every Neighborhood
Not everyone will download ChatGPT right away. But what if they could walk into a city building and use AI like any other public service?

Chicago could transform public libraries and community centers into AI Service Hubs. These would be places where anyone can get help using AI tools to navigate daily life, staffed with trained support specialists.
A job seeker could use AI to draft a resume or practice interview questions. A small business owner might create a social media campaign using generative AI. Residents could access multilingual assistants to help translate housing documents or understand local school options.
Just as libraries once introduced public internet access, these hubs would essentially do the same but for AI.
AI Upskilling & Reskilling
The rise of AI is reshaping the job market faster than any previous technology. But right now, access to AI education is still limited. We need to build new onramps, and Chicago can lead the way.
We could start by launching AI literacy and skills programs in public libraries, community colleges, and city-run workforce centers. These wouldn’t be generic coding bootcamps. They’d be tailored tracks.
The key is to make it practical and local. Offer certification pathways recognized by employers. Provide stipends or paid apprenticeships. Align it all with real economic opportunities, especially in sectors like healthcare, transportation, and public safety where AI is already being deployed.
But Can We Afford It?
Chicago isn’t flush with cash. Any new initiative has to justify itself.
A citywide AI assistant would require a meaningful upfront investment but could save real money by reducing 311 volume, cutting permitting confusion, and opening doors for developer integrations.
Neighborhood AI Service Hubs could be piloted at low cost and could support small business growth, job seekers, and even attract corporate sponsors or grant funding. Think: “This lab powered by Google” at your local library.
AI upskilling programs could be co-funded by employers looking to hire trained talent, and supported by federal or philanthropic grants tied to workforce development or climate tech.
These aren’t sunk costs. They’re investments in operational efficiency and economic growth.
If Dubai can put ChatGPT in every resident’s pocket, Chicago can go a step further by giving people the tools to understand and thrive.
Let me know what you think.
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📆 Events Around the City
AI Tinkerers Chicago June Meetup
Hosted by Drive Capital and Bonsai
Tuesday
BioTech Fermenter: Chicago's Biotechnology Meetup
Tuesday
Tech Pulse 2030: AI Labs Shaping Tomorrow
Tuesday
🗞 Previous Newsletters:
👋 See you next week!
Rural universities are struggling with falling enrollment but @UofIllinois is an exception.
Enrollment is up 36% since 2010 while Western Illinois is down 47% over the same period.
UIUC’s growth reflects years of investment in engineering, research, and global talent.
— #Landon (#@landon20s)
2:32 AM • May 26, 2025