Alex Kotlowitz

Cassius Tae

The DIY spirit is often made perfect in the city of Chicago. Few others embody that vibe like Cassius Tae [https://www.youtube.com/channel/UCjiHw4YMab65da9uX9nBXuA]. In this chat, you’ll hear how Cassius crafted a life as a writer, designer, and rapper. Plus, Cassius shares how he kicks up his compassion as a mentor to creators with an event called The Writers Room. Get full access to Kevin's Substack at kevincoval.substack.com/subscribe [https://kevincoval.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Bobby Whittingham

This is a conversation about being called home to the family business. Bobby Whittingham is a 4th generation entrepreneur in one of Chicago's most storied industries. In this chat, Kevin tracks the story of Bobby's great grandfather, who started a meat packing legend with a 100 bucks in 1947. How is it that Whittingham Meats [https://www.whittinghammeats.com/pages/story] has survived nearly eight decades? Bobby drops some truths about the grit that rules his hometown. Get full access to Kevin's Substack at kevincoval.substack.com/subscribe [https://kevincoval.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Holley Brandchaft-White

Why are some of us drawn to spaces where people are doing hard things? Holley Brandchaft-White [https://www.instagram.com/holley_shft/] has chosen that life, and has something to say about it. In this convo, Kevin talks with Holley about her journey from being a social worker in trauma units to using an MBA in pursuit of mental health innovation. Holley is the co-founder of SHFT Behavioral Health [https://www.shftbh.com/about], Chicago’s first emotional wellness urgent care center. You’ll hear how our city’s resilience and segregation often collide in ways that hurt and help. Get full access to Kevin's Substack at kevincoval.substack.com/subscribe [https://kevincoval.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Shadow Master

This conversation may be the master class on defining what Chicago has fused into hip hop culture. As Shadow Master [https://shadowmastermc.bandcamp.com/album/art-of-a-lion] says, “We have flavors that don’t exist anywhere else.” In this chat, Kevin talks with the creator and curator of 606 [https://www.youtube.com/@606chicago8], the longest running open mic freestyle session in the world. You’ll catch how music flowed from every hallway of Shadow Master’s family house on the West Side. It turned him into a singer, before he was an MC. Plus, you’ll hear his vision for turning hip hop into therapy at neighborhood schools. Catch 606 Chicago every Tuesday night at Boulevard Sports Lounge [https://boulevardsportslounge.com], 2645 West North Avenue in Humboldt Park. Get full access to Kevin's Substack at kevincoval.substack.com/subscribe [https://kevincoval.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Alex Kotlowitz

How does one land not so purposefully in this town? Alex Kotlowitz [https://www.alexkotlowitz.com/] has a story or two to share about that. In this conversation, Kevin talks with Alex about the many ways Chicago invaded his soul as a writer — then a resident. His journalism is steeped in empathy. It’s one of the reasons he is able to tell the most difficult stories [https://www.penguinrandomhouse.com/books/95252/there-are-no-children-here-by-alex-kotlowitz/]. Get full access to Kevin's Substack at kevincoval.substack.com/subscribe [https://kevincoval.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]