✍🏽 Welcome to Landon’s Loop: your weekly read on Chicago startups!
In this week’s edition #127:
- Reflecting on Drive Capital’s Annual Summit
- Chicago make list of top 10 funding markets for first time
- 8 tech events in Chicago this week
Building Between the Coasts: Reflections from TAM
Last week I was in Austin for our firm’s Annual Summit, which we call TAM (The Annual Meeting)

Our goal was simple: bring together top founders, investors, and LPs building between the coasts under one roof.
The Heartland is vast. Its scale can make it harder to find the right partners, especially from afar. Yet that same scale represents a multi-trillion dollar economy waiting to be connected.
As AI reshapes industries from manufacturing to healthcare, the biggest impact will be felt in places where those industries live: between the coasts.
Innovation isn’t tied to one city.
What We Heard
We hosted an incredible lineup of speakers who highlighted just how diverse and powerful our regions are:

Mark Suster from Upfront Ventures spoke about why Los Angeles has become a hotbed for aerospace innovation.
Zachary Mears, SVPo f Strategy & Growth at Anduril, explained why their company chose Columbus as the home for its next-generation manufacturing plant, the largest of its kind.
Ed Hallen, who co-founded Klaviyo, shared lessons on why relentlessness separates the founders who succeed from those who do not.


I also led a panel with Alex Cohen, founder of Hello Patient, on founder-led storytelling. My core argument was the internet has no geography. Distribution doesn’t depend on your zip code.

We discussed how the internet is the great leveler for founders outside SF and NYC to share uniquely grounded stories.
What I Took Away
My favorite part of TAM wasn’t the stage, it was the hallway.


Seeing our entire portfolio in one place was energizing.
At Drive, we invest at every stage, from pre-seed to pre-IPO. So bringing our founders together and letting early CEOs learn from later-stage operators, and vice versa is what made it feel so special.


Building between the coasts is rewarding.
And after a week in Austin, I’m more convinced than ever: the future of innovation will be written in the Heartland.

Today we're welcoming 150 CEOs from startups across the country and 50 VCs to Austin for TAM.
The vision for TAM is to gather the best of the best from a large geography (𝐴𝑚𝑒𝑟𝑖𝑐𝑎) to one city for one day.
Should be fun.
— #Drive Capital (#@drivecapital)
1:41 PM • Sep 17, 2025
📊 Chart of the Week
Company building is more than raising money. Founders should always optimize for building where their customers are and where they have an edge in talent.
Still, it’s great to see Chicago make Carta’s top 10 funding list for the first time ever.

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📆 This Week’s Chicago Tech Events
AI in B2C Marketing
Tuesday
1 Million Cups
Wednesday
Chicago Data Night: Haifeng Xu (UChicago)
Hosted by Drive Capital and UChicago Data Science Institute
Wednesday
Nucleate Chicago: Activator Virtual Info Session
Wednesday
Consumer Chi Coffee Club with MFD and JP Morgan
Thursday
Governance for Hardware Startups
Thursday
WCXO INSIGHTS: AI Infrastructure for Financial Services by Supermicro & NVIDIA
Thursday
PROJECT PYGMALION HACKATHON
Hosted by SimCare and Drive Capital
Saturday