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✍🏽 Welcome to Landon’s Loop: your weekly read on Chicago startups!
In this week’s edition #118:
- Where Chicago fits in the AI stack
- Highlights from my fireside chats with Alex Jones and Brad Feld
- Getting ready for TechChicago Week ‘25
🔙 Last Week in Chicago
We hosted a fireside chat with Alex Jones from Hallow to discuss what it takes to scale a consumer app in Chicago 👇🏽

Right after, we welcomed Brad Feld to the office for a conversation on the state of AI and his new book, Give First. 👇🏽

Joined the Layer Zero Podcast to talk about why the Midwest is gaining momentum in tech 👇🏽
I was a guest author for the Start Midwest newsletter (highly recommend), where I shared a behind-the-scenes look at our TechChicago Week lineup 👇🏽
🤖 Mapping Chicago's AI Economy
I've long said that AI’s future won’t be shaped by just code, but by the infrastructure behind it. Power lines. Cooling systems. Data centers. Physical infrastructure.
And the cities that get this trifecta right (power, people, and purpose) will dominate.
Chicago checks all three.

Let’s break down what Chicago’s “AI play” looks like across our economy, talent, and adoption on the ground.
Foundation of Infrastructure
AI isn’t just some floating intelligence in the cloud. It’s a power-hungry beast. Training GPT-4 used about as much energy as it takes to power 5,000 homes for a year.
AI starts with physical stuff: power, connectivity, compute, and space.
Chicago has what AI needs to run:
Nuclear power. Water-cooled systems. Industrial real estate.
65,854 jobs in core infrastructure, leading to $24.3B in output.
Energy workers here earn nearly $200K a year.

Pipeline of Talent
Chicago doesn’t scream AI, but maybe we should. We’re a top STEM city, churning out researchers and engineers who don’t just post threads, they ship:
136 AI papers published last year
1,103 AI patents
32m NSF ACCESS credits tapped by local researchers to train at scale
373 AI startups have launched here since 2023
The point? Chicago doesn’t need to “catch up.” It’s already building.

Early Signals of Adoption
One out of every three jobs here is exposed to generative AI.
Chicago isn’t a monoculture. It’s not all SaaS or search engines. It’s healthcare, logistics, finance, insurance, manufacturing. If AI’s going to reshape the real economy, it needs a place to plug in.
That’s Chicago: home to the third-highest number of Fortune 500 HQs in the country. 26% of local companies are already data-ready, and 22% are cloud-ready.

Translation? Once leadership gives the green light, AI isn’t stuck in pilot mode, it will move to full-scale production, fast.
What to Expect
Chicago is a city of builders and implementers. This is where AI gets out of the lab and into the warehouse. Into the ER. Into the budget spreadsheet.
Infrastructure. Talent. Industry.
It’s not a buzzword. It’s an actual playbook.
Chicago isn’t just betting on AI. We’re executing it.
💰 A Banking Partner for the Builder Journey
Silicon Valley Bank, a division of First Citizens Bank, is the bank of innovative companies and investors.

With 40+ years of dedication to our sector, SVB has deep experience banking investors and innovation clients.
Their entire business, from solutions and technology to credit policy and beyond, is purpose-built for high-growth companies and investors and delivered at the speed they need.
If you're interested in learning more about SVB - Book a Meeting with Chicago’s own Nick Jones today

📆 This Week’s TechChicago Week Events
TechChicago Week is here! Here are my top event picks for the week ahead:
Powering AI in the Heartland 🚙
Hosted by Drive Capital
Monday
FoundersCHI
Monday
TechChicago Week KICKoff
Monday
Founders N' Funders: Chicago VC Reverse Pitch
Monday
UChicago Tech Ventures Demo Day
Monday
TechPalooza 🚙
Hosted by Drive Capital and 1871
Tuesday
Founder Night Out: In-Person Startup Networking in Chicago
Tuesday
A Founders & Funders Happy Hour: TechChicago Edition
Tuesday
Book Launch: 'Sweaty Equity' Book by Mike Shannon
Tuesday
Coffee & Capacitors: Climate x Hard Tech Breakfast
Tuesday
AI Action Lab: From Fear to Forward Motion for Your Business
Tuesday
Chaos to Clarity: How Process Mining is Changing Tech Leadership
Tuesday
Capital Summit
Tuesday
I have VIP codes. Email me if interested
Lenny’s Newsletter Meetup
Tuesday
AI Agents in Healthcare Symposium 🚙
Hosted by Drive Capital, JP Morgan, and Tempus
Wednesday
Gemini API Sprint - Chicago
Wednesday
Chicago Digital Health Tech Breakfast Meetup at TechChicago Week 2025
Wednesday
Pixels & Prosecco: Women in Tech Mixer
Wednesday
Reinventing Industry: Clean Energy and Sustainability
Wednesday
Humans First Venture Investing
Wednesday
Josephine Collective Founder Pitch Event
Wednesday
Pre-Seed Between the Coasts 🚙
Hosted by Drive Capital, Cooley, Matchstick Ventures, and Bernstein
Thursday
Early-Stage B2B Founders & Funders Breakfast
Thursday
Legal Considerations for Quantum Computing and AI
Thursday
Nerds Like Me
Thursday
Private Airport Hangar Pitch Competition
Thursday
Jews in Tech Breakfast
Friday
AI Strategy Live Planning Session
Friday
🗞 Previous Newsletters:
👋 See you next week!
New crane 🏗️ spotted from Fulton Market today
Now we just need about 100 more
— #Landon (#@landon20s)
1:40 AM • Jul 16, 2025