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

Yuta Katsuyama moved to Chicago to study design and business — and quickly noticed something missing: onigiri. What started as a personal craving became a brand now stocked on over 60 shelves across Chicagoland. Yuta talks about bridging Japanese food culture and American entrepreneurship, and what it means to build something from pure necessity.

https://www.onigirikororin.com/
https://www.instagram.com/onigirikororin_riceballs/
https://www.instagram.com/yuta.kororin

One meal at Franklin Barbecue lit a fire in Charles Wong that spreadsheets never could. Since then, he's been quietly building something special — Texas-style BBQ layered with Chinese and Vietnamese heritage, served up through pop-ups and residencies that turned first-time customers into loyal community. After a heartbreaking near-miss on a food hall space, Charles regrouped, reflected, and set his sights on what's next: a brick-and-mortar that he hopes will finally give his community — and his team — a place to call home.

https://umamicue.com/
https://www.instagram.com/umamicue/

What if the most powerful thing you could say to someone wasn't advice — it was I believe you?

We sat down with Holley Brandchaft-White, licensed clinical social worker, former Lurie Children's Hospital ED clinician, and co-founder of SHFT Behavioral Health — Chicago's first mental health urgent care center for young people and families. Returning guest Steph Krim of Good Things Vending joins as co-host.

After a decade in the children's ER, Holley saw firsthand that most people in mental health crises didn't need to get that far. SHFT was built on that truth: meet people earlier, before the small things pile up into something unbearable. But it's not just about where you go — it's about what the environment makes possible. The same amount of time with a patient can feel entirely different when there are no monitors beeping, no signatures being rushed, no sense that someone is already halfway out the door. SHFT changes everything.

Whether you've been in therapy for years or never considered it, this one might shift something in you.

If you or someone you know is struggling, you don't have to wait for a crisis to ask for help. Call or text 988 to reach the Suicide & Crisis Lifeline — free, confidential, 24/7 support for mental health, substance use, or emotional distress. Save it in your phone. 911 is for immediate physical emergencies. 988 is for everything that lives in between.

https://www.shftbh.com/

https://www.instagram.com/holley_shft/

https://www.instagram.com/goodthingsvending

Tony is back for round three! He was on the show five years ago when he was just establishing the professor pizza brand and three years ago when he partnered with the Atomic Hospitality group to provide his pizza on a rooftop in west loop. Since then, he's been approaching two years with the 50/50 hospitality group at their old town location. He just opened a slice shop in west town as well as in Boston. This is an episode about our love for Chicago food, the beauty of collaborations, and future endeavors like bringing frozen pizzas to the market. Please enjoy my conversation with Tony Scardino. 

https://professorpizza.com/

https://www.instagram.com/professorpizza/

https://www.instagram.com/professorpizzawesttown/

Our next guests are the dynamic duo behind AB Law. Despite being located on the north side of the city, they are helping individuals experiencing a variety of hardship obtain legal status across the country. Their friendship was formed while working together at a restaurant and blossomed into a partnership after working at two law firms previously. We reflect on their personal ties to immigration and why they’ve dedicated their lives to helping others obtain their citizenship. Please enjoy my conversation with Anastasiia and Mia of AB Law. 

https://chicagoablaw.com/

https://www.instagram.com/lawyeranastasiia/

Our next guests are riding the wave of aloha washing over the chicagoland area. They are the yin to each other’s yang. We reflect on the various iterations these lunch plates have taken from pop up tents and food trucks to their first brick and mortar in Highwood, IL. Today, they’re opening their second location in South Loop near the Sears Tower. Congrats friends. Please enjoy my conversation with Nate and Dianne of the Da Local Boy. 

https://dalocalboy.toast.site/

https://www.instagram.com/dalocalboy/

Our next guest is the owner of Ragadan and A Pizza Pie in Uptown. He reflects on his family’s journey to Oklahoma City from Amman, Jordan. It’s not too often you find a joint that serves great burgers and falafel. Despite the fast casual nature of his restaurants, he’d like to find a way to bring more traditional Jordanian dishes like mansaf to the community. The question is what it’s going to cost him. Please enjoy my conversation with Danny Sweis. 

https://ragadan.com/

https://www.apizzapie.com

https://www.instagram.com/ragadanrestaurant

https://www.instagram.com/a.pizza.pie

Our next guests are two college friends that host album listening parties around the city. What started as a way to stay in touch with their group of friends has expanded into a third space for like-minded individuals. Whether it’s your hundredth or first time listening to an album, all are welcome. Please enjoy my conversation with Grant and Kalium of The Heavy Rotation.

https://www.instagram.com/the.heavy.rotation