✍🏽 Landon’s Loop #182

🎙️ Chicago Futurist: Betsy Ziegler

My earliest memory in Chicago tech was at 1871. I was a junior or senior at DePaul, building a podcast with my best friend, who passed away a few years later. We spent a lot of days at the Merchandise Mart, borrowing 1871's pod space. So sitting down with Betsy Ziegler from 1871 meant a lot to me.
If you're new here, 1871 is Chicago's startup hub. It's a nonprofit that opened in 2012 and spent more than a decade at the Merchandise Mart.
In February 2025, Betsy told members 1871 could no longer sustain the real estate and would leave the Mart.
9 months later, Thanksgiving week, she sent the city another email that she had been diagnosed with ovarian cancer.
We filmed this interview on Oct 1, two days before she hit 6 months of remission.
When did you realize 1871 after COVID wasn't what it was meant to be?
BZ: The original thesis of 1871 worked. The idea, I mean, certainly at that time, there was nothing else like it, right? And putting everything under one roof. And the idea of somebody being virtual was like, I mean, it wasn't even a word that people used. So the idea worked.
As soon as the pandemic hit, we knew that the model had shifted because people reacted very abruptly to that. And so the real estate model, which was the underpinning of the business, 1871's a nonprofit, so we had a real estate business model, we knew was upside down pretty quickly.

How would you define 1871 today?
BZ: I still say we're infrastructure. But infrastructure detached from an address. And so when I think about the role of 1871, I mean, our job is not about a desk. Our job is about increasing people's probability of success and shortening their timeframe to reach it. Like, that is our job. And that storyline is actually much more simple in this business model than it was in the Mart when I had a rent bill I had to pay. Right? Not that they were necessarily in conflict, but it wasn't always a mission orientation because I had a business to run. I still have a business to run, but in a very different cost structure

SpotHero, which started in 1871, got acquired by Uber. How special did that feel?
BZ: When that happened, it felt very personal to me and to the 1871 team and board and community. It was so amazing. And Mark Lawrence is just an extraordinary leader and built this amazing team. They don't talk about themselves a lot, right? They have enormous pride, but they're not out there like pounding their chest for themselves, which again, is true for many people in Chicago. And so part of it was like, how do we help do that? How do we help bring the celebration to them, which is part of why we opened the Momentum Awards with that.
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🚆 Chicago Builds: Third Rail
I just released the official schedule for Chicago Builds: Third Rail on November 12th

Chicago Builds: Third Rail is a summit on how people and goods move through this city: autonomy, freight, micromobility, and rail. 250 founders, operators, engineers, public officials, labor leaders, and investors. Doors open at 2pm.


💴 The Head Tax is Back
On Wednesday, Mayor Johnson released a $17.6B 2027 budget to close an $882 million budget gap, and he recommitted to bringing back the corporate head tax.
The new version charges companies with more than 125 employees $25 per worker per month and would raise about $101 million a year. Employers with workers in Chicago's designated "socioeconomically disadvantaged areas" could get credits that cover it. The mayor now is calling it the "equitable employer tax."
The council already said no. Last month, 29 alders in the Budget Accountability Coalition wrote that they won't support a head tax or "any levy that makes it costlier to keep and create jobs."
The part founders should watch is the one getting fewer headlines. The budget raises the personal property lease tax, the one that hits equipment rentals and cloud computing and is already the highest in the nation, from 15% to 20%. The city expects about $234 million from those changes.
The head tax mostly hits big employers, and it looks headed for another loss. The lease tax hits every two-person startup paying for cloud software, which is exactly the kind of company Betsy is betting on. I asked her how founders get heard at City Hall.
Her answer: making sure "City Hall has an appreciation for what the life is like for these young companies."
Budget hearings run for the next three weeks, and the council has until the end of the year. If you’re building a companu in Chicago, now is the time to tell your alder what 20% costs you.
📅 Who’s Hosting This Week in Chicago
WoCS Chicago x Rod Cherkas: Book Launch
Hosted by Drive Capital
Tuesday
TechWalk | Chicago, 10/27
Tuesday
Scratchpad Chicago: Session 70
Tuesday
Lunch and Learn - From Hyde Park to the Boardroom
Wednesday
Supper Club: Compute Chicago
Wednesday
Chicago CISO XC Executive Dinner
Wednesday
OpenAI Forum
Thursday
Chicago AI Builders Meetup: From First Build to Production
Thursday






