In partnership with
✍🏽 Landon’s Loop #150
What’s in the Loop:
🎙️ Chicago Futurist Vol. 11 with Brendan Reilly, Candidate for Cook County President
💼 3 AI Roles in Chicago
🍀 St Patty’s Vibecoding Hackathon Recap
📅 8 Events in Chicago This Week
🎙️ Chicago Futurist: Brendan Reilly, Candidate for Cook County Board President
Alderman Brendan Reilly represents Chicago’s 42nd Ward in the heart of downtown and is running for Cook County Board President.
Ahead of tomorrow’s election, we spoke about how local government can better support builders and founders, from fixing policies like Chicago’s cloud tax to modernizing procurement and treating public data as infrastructure.
Here’s our conversation:
What’s one policy decision you saw up close that unintentionally slowed innovation or investment in the city?
BR: The "Cloud Tax" (Lease Transaction Tax) on remote software and data processing. It was a short-term, reactionary revenue grab by the city that sent a chilling message to the global tech community, that Chicago is a place where digital scaling is penalized. It forced startups to think twice about expanding here.
As County President, my vision is to shift the local government mindset from taxing innovation to incentivizing it, ensuring we are structurally competitive with places like Austin or Miami.
Explain the structural incentives inside government make tech projects so hard to get right?
BR: The core issue is that government procures technology focused entirely on rigid specifications and risk avoidance. Procurement is designed to prevent lawsuits, not to deliver a seamless UX/UI. We reward vendors with further contracts to avoid additional procurement, even if the final product is obsolete or late on arrival, rather than iterating via agile development.
To fix this, we need to completely overhaul how the County buys tech. We move toward outcome-based procurement and create "talent tours of duty" to bring top-tier engineers out of the private sector and into public service for two-year sprints.
Could AI help modernize how Cook County assesses property values and improve transparency for residents and businesses?
BR: Predictability is the absolute bedrock of investment. Right now, our property tax system feels like a black box. We need to open-source the mass-appraisal algorithms. Residents and founders shouldn't need an expensive, politically connected lawyer to decipher their tax bill.
By deploying AI to continuously audit and refine assessment models against real-time market data, we can guarantee assessments are rooted in reality, allowing businesses to forecast their runway 10 years out instead of dreading the next triennial reassessment.
How could we unlock public data in a way that drives innovation while protecting privacy?
BR: It looks like creating a County Data Trust, where we move away from "black box" third-party contracts, like the recently renewed Apriss Contract, that allow vendors to monetize or inadvertently leak our data to third-parties. We must treat data as a public asset by asserting sovereign control and implementing a zero-trust architecture, allowing researchers and startups to build on anonymized datasets without compromising the privacy of our residents.
By creating a secure Sanctuary API that filters for high-level transparency while strictly blocking the bulk data transfers often exploited by outside agencies, we can ensure that our data infrastructure serves as a engine for innovation rather than a liability for our neighbors.
Why does government rarely operate with an experimentation mindset?
BR: Because in government, a failed experiment is unfortunately a front-page scandal. It’s not just investment money you’ve wasted, but taxpayers dollars. In the startup world, it’s a necessary pivot. We have engineered the bravery out of our civil servants. To change this, we must establish formal regulatory sandboxes, controlled environments where startups can test new tech (like autonomous transit or blockchain-based property records) with relaxed regulatory friction. We need to give our departments the political cover to try things that might fail, because that is the only way we will ever discover what succeeds.
What would it take to become one of the leading regions for building tech companies?
BR: We have to stop ignoring our advantages! We have unparalleled national labs (Argonne, Fermilab), world-class research universities, and a legacy of manufacturing. Success means creating physical and economic "Quantum and Cleantech Corridors" with zero-friction zoning for R&D-heavy startups. Most importantly, it requires building dedicated commercialization pipelines, which ensure that a breakthrough at the University of Chicago can become a Series A company in the West Loop, funded by local capital and supported by County grants.
How can we play a role in accelerating the conversion of underused office space into housing and maybe even physical communities for founders?
BR: Ideally, the Loop is evolving from a 9-to-5 workplace into a 24/7 hyper-connected neighborhood, but the math on adaptive reuse is incredibly difficult. The County’s role is to make that math work. We need to streamline property tax incentives specifically tailored for complex office-to-residential transitions and ensure we aren’t taxing these buildings into obsolescence before they break ground.
Beyond housing, we should be incentivizing the conversion of commercial real estate into urban vertical farming, biotech lab space, and light-manufacturing incubators.
If you could remove one bureaucratic friction point that slows entrepreneurs down today, what would it be?
BR: Permitting Purgatory. Whether it’s a zoning variance or a simple business license, the lack of a unified, digital tracking system drains capital and kills momentum. I would implement a digital clock on county approvals. If the bureaucracy doesn't process your application or give you a specific reason for delay within 30 days, your approval is automatically granted. We need to move at the speed of business, not the speed of paper.
When we revisit this conversation ten years from now, what would success look like for Cook County?
BR: Cook County will be recognized globally as the great turnaround story of the decade. We will have slowed population decline, stabilized our tax burden through a modernized commercial tax base, and fully digitized our government services. Success looks like the brightest minds in the world choosing to come to Cook County to solve the hardest problems in climate, health, and tech, because they know their local government is an active partner in their success.
People want density, reliability, and opportunity. They want a city where the public transit actually works, the streets are safe, and the local government functions like a responsive, intuitive app, not the classically dreaded DMV visit.
Quality of life is no longer just a perk; it is our primary economic development strategy.
The Illinois primary elections are Tuesday March 17. Make sure to exercise your right to vote and support leaders who are serious about growing our city and strengthening its future.
💼 Who’s Hiring in Chicago
Stealth Startup — AI-Native Sales / Account Management
Early GTM hire at a Chicago startup building an AI-first sales platform. Ideal for someone who understands both startups and modern AI tooling.
→ Learn more
Tractorbeam — Forward-Deployed Engineer
Chicago AI lab hiring engineers who sit at the intersection of strategy and implementation, building real AI systems for enterprise customers.
→ Learn more
Cook County — Cloud Data Platform Manager
Opportunity to help modernize public infrastructure by leading cloud data systems for one of the largest counties in the U.S.
→ Learn more
Hiring in Chicago?
List your role in Landon’s Loop and get it in front of tens of thousands of engineers, PMs, operators, and builders across the city.
🍀 St. Patty’s Vibecoding Hackathon
While most of Chicago was out celebrating St. Patty’s on Saturday, we had a different kind of energy in the office.
We hosted the VibeCoding AI Hackathon with DeepMind at Drive Capital.
With less than a month of promotion, we saw over 450+ total RSVPs all for a 125 person capacity event.
All around Fulton Market, lines stretched outside bars. Inside our office, the lines were for demos.
We had builders spread across every corner of our office. 30 presentations. Tables full of laptops. Endless coffee.
A friend said something last week that stuck with me: AI has the power to bring people together. Especially around vibecoding. People often say AI will make us more distant from each other. I actually think the opposite is happening.
This technology is moving incredibly fast, and communities are looking for places to build and learn from each other. We see it every month at our AI events.
They started as meetups for engineers and technical builders. But lately we’re seeing something new. More people who aren’t technical are showing up because they want to understand what’s happening and learn how to participate.
That curiosity is powerful.
Chicago has always been a city of builders. Now we’re seeing that same energy show up around vibecoding.
The Architecture Behind AI-Native Revenue Automation
Most “AI finance” tools guess. Finance can’t. This white paper explains how AI-native revenue automation combines reasoning, deterministic math, and commercial context to automate billing, cash, and close—without sacrificing accuracy. Read the architecture behind AI-native revenue automation.
