This week, a sit-down with the founder of World Business Chicago. Waymo and Springfield get closer on an Illinois AV bill. Along with events happening around Chicago.

Let’s dive in:

Paul O'Connor founded World Business Chicago, the official public-private economic development agency for the City of Chicago. Mayor Richard Daley asked him to run it.

The organization he built from scratch is still running the same play, at a bigger scale. WBC's latest State of the Economy report puts the region at $929B in GDP, the third-largest metro economy in the country, with 223 expansions, relocations, or new market entries last year, a record on their count.

The headline on Paul's time at WBC is Boeing. Headquarters from Seattle to Chicago. He walked me through how it actually happened.

WBC started as the Chicago Partnership for Economic Development. The Commercial Club asked him to take World Business Chicago. Paul asked for $100,000.

"We spent the first eighteen months building a regional database," he said. "And then Boeing came. Daley gave us the Boeing lead. And then we won."

That database is still a standing research center putting out important information on our city every year.

Paul dates the win to 2000. The move was announced in March 2001 and completed that September.

The database claim holds up. A June 2001 letter he wrote for the Chicago Fed already leans on compiled regional numbers. A 2002 WBC release under his name cites BLS data comparing Chicago to Atlanta, NYC, SF, and San Jose.

Paul's point today is not that 2001 was better. It's that the work compounded.

"The little seeds that were planted then, they are trees now."

Paul didn't stop being an urban strategist when he left WBC. He spent the next decade at SOM's City Design Practice, thinking about cities the way an architect thinks about load-bearing walls. That's the lens he brought to the second half of our conversation.

The old WBC model was one pitch for every industry. Paul's generation built the regional database, then sold Chicago as a whole to whoever was listening.

The newer approach, organizing by industry, is already working here in pockets. mHUB for manufacturing. Matter for healthcare. Portal Innovations for life sciences. Each is built around one industry's specific problems, not a generic playbook.

Where Paul lit up was the diversification point. Chicago's economy doesn't lean on one industry the way Boston leaned on science or Detroit leaned on cars. No sector clears thirteen percent of the total here in Chicago.

"Because of the diversification of the economy, this is the perfect place to apply AI," he said.

I pitched Paul a version of this that goes even further. A simple way to make AI work for every Chicagoan.

Imagine citywide deals with the major model providers. Not a pilot for a few downtown offices, but free credits that any resident can claim, whether they’re running a SMB on the South Side, taking classes at a city college, or figuring out a side project.

More classes. More seminars. Neighborhood workshops that meet people where they already are. A city that treats AI reskilling and upskilling as basic infrastructure.

The same idea as putting computers in every library when the internet launched. We understood then that access could not stop at the people who already had it, so we built it into the places everyone shares.

It reminded Paul of the Boeing play. 18 months of unglamorous work first. Then, when the moment shows up, don’t say no.

The seeds are trees. The question is whether we still know how to plant.

Last week, I sat with Lara Dailey from Waymo, Rep. Kam Buckner, and Senator Michael Hastings at Morningstar during 1871's policy morning.

We spent 30 minutes talking about what it actually takes to put autonomous vehicles on Chicago streets.

Lara led with safety. 94% of serious injuries come from human error.

Fatigue, distraction, impairment. That is what Waymo’s are built to take out. Hastings added the hardware: 360-degree lidar and radar, coverage a person in the seat doesn’t have.

No one on the panel was selling this as a CTA killer. In SF, 36% of Waymo trips connect to transit. The Chicago gap they named is South Side and West Side deserts, plus seniors and people who cannot drive. Complement, not replacement.

Kam and Hastings said Illinois is extremely close on an AV bill this fall. Liability, data preservation, first-responder protocols will be a main priority. The cars are already mapping Chicago.

The push for Waymo is more than just for the vehicles themselves. Lara put local infrastructure following Waymo north of $100m which could include depots, charging, maintenance, fleet operators, and cleaning. We spoke a lot about how even when you don’t see a driver in the seat, there is more to the whole operation.

At the end, everyone agreed: Chicago is the hard test. We have multiple seasons here including winter and construction. If the stack works here, it works everywhere.

Follow me on Twitter and Instagram