What does it actually take to make Chicago more affordable, safer, and functional? Joe Holberg — political outsider, former teacher, Google alum, and tech entrepreneur — is running for mayor with a platform built around housing supply, fiscal discipline, and a friendlier environment for businesses of every size. In this episode, Joe digs into the CTA safety crisis, Chicago's permitting problem, the parking meter deal that still haunts the city's budget, and why getting kids to school every day might be the single most important lever in the city. No political jockeying — just problem solving.

www.joeforchicago.com
https://www.instagram.com/joeforchicago/

In this episode, I pass the mic to Charles Wong of Umamicue and Episode 182. He hosts Shawn Smith of Heffer BBQ along with brothers Sam and Stephen Lee of K-TEX BBQ. They share their individual journeys into BBQ and where they’re currently at. They share notes on what has and hasn’t worked, manifesting a brick and mortar, and reflect on what Chicago BBQ can be. It was truly a pleasure to take a back seat as they went to depths I could have never gone to. I hope to host more of these roundtables in the future.

https://www.instagram.com/umamicue

https://www.instagram.com/therealhefferbbq

https://www.instagram.com/ktexbbq

John Carruthers didn't set out to raise $100,000 for Chicago nonprofits. He just wanted to do something that felt useful when the world stopped making sense.

When the pandemic hit, John — a writer and lifelong pizza obsessive — felt the helplessness that most of us did. What started as a weekly family ritual became something stranger and more beautiful — a secret alley pop-up, where strangers donate to John’s monthly charity of choice, show up to an alley, and eat great pizza.

That's Crust Fund Pizza. And it's become one of the most quietly meaningful food projects in this city.

In this conversation, we reflect on the current state of journalism, how John fell in love with Chicago, and how his love of making pizza has taken him across the world.

Find John at crustfundpizza.com and on Instagram at @nachosandlager