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✍🏽 Welcome to Landon’s Loop: your weekly read on Chicago startups!
In this week’s edition #115:
- My upcoming fireside with Brad Feld, co-founder of Techstars
- 4 must-attend events happening this week in Chicago
- A look at Chicago companies that hit $100M+ valuations by founding year
- A local dev launched a ChatGPT trained on Chicago city data
🔙 Last Week in Chicago
Norton Rose Fulbright interns visited our office to learn about the Chicago venture landscape
Big thanks to my good friend George Khalife for organizing. 👇🏽
We held our 19th AI Tinkerers Chicago meetup
Our tinkerers community is growing rapidly. We now have over 1,300 community members and 120+ demo submissions in the last 6 months.👇🏽
ChatGPT on Chicago City Data demo’d at our AI Tinkerers Meetup
Last month, I shared a blog about how Chicago could use AI to better serve residents, including an idea for a city-trained GPT to answer questions about zoning, licenses, and transit.
After reading the blog, Mirza Baig (a local AI engineer) built AskCHI just days later. It's a chatbot trained on city data that helps residents ask questions, pay tickets, and submit service requests. 👇🏽
Drive Capital Head of Marketing Nils Root speaks to our founders
Nils stopped by our Chicago office to discuss content, PR, and events with our seed companies. 👇🏽
📖 Techstars Co-Founder Brad Feld Is Coming to Chicago
I’m teaming up with Bernstein Private Wealth to host a fireside chat with the legendary Brad Feld!
Brad Feld is a partner and co-founder of Foundry. He’s been an early-stage investor and entrepreneur for over 35 years, since founding his first company, Feld Technologies, in college.
He’s the author of several books on entrepreneurship and VC. Even started blogging in 2004 before VC Twitter existed.
In 2006, Brad co-founded Techstars, which has funded over 3,700 companies across 55+ global accelerator programs, with a portfolio valued at $27B+ and 15 unicorns including DigitalOcean, SendGrid, and Chainalysis.
Brad’s philosophy is simple: give first without expecting anything in return. He’s put these lessons in his new book Give First, which is a philosophy that encourages giving time, resources, and expertise without expecting anything in return.
It goes beyond “paying it forward,” promoting a continuous, optimistic, and empathetic mindset that creates positive feedback loops for individuals and entire communities.
The book shows how embracing Give First can help build vibrant startup ecosystems and transform you into an exceptional mentor.
In our fireside conversation on July 17th, we’ll explore how generosity, mentorship, and long-term thinking have shaped his approach to investing and leadership. It’s not a book talk, but his latest release, Give First, will definitely help frame the discussion.
Reply to this email if you’re a founder that’s interested in attending!
📊 Chart of the Week
This is worth checking out: Jackson Bubala from Motivate Ventures pulled data on Chicago’s tech scene over the past 50 years.
One of the charts tracks Chicago companies that reached $100M+ in value by founding year. One year stands out: 2014.
It was a class that had a mix of logistics, industrial-tech, and applied AI. These teams built during a capital-efficient era, focused on fundamentals, and many scaled into category leaders.
$100M matters. It signals traction, market fit, and staying power. Crossing $100M is often the milestone that defines real impact.
If you're building in Chicago today, the questions that I have are:
How do we bring back that 2014 energy
Which industries will define the next era of Chicago tech
💰 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
📆 Events Around the City This Week
Quick Reminder: TechChicago Week is right around the corner starting on July 21st! Make sure you take a look at our events
Chicago Female Founders & Friends
Monday
ClickHouse + Docker AI Night
Tuesday
Data Poisoning Discussion
Wednesday
Polsky Exchange Capital Access - Mona Ventures
Thursday
🗞 Previous Newsletters:
👋 See you next week!
Long Chicago
— #Landon (#@landon20s)
2:59 AM • Jun 25, 2025
