Segment 1: Tom Fortino, Founder and Principal, Alpha Wealth Group, and host of “The Alpha Wealth Hour” on WGN Radio, joins John to talk about the impact of the Israel-Iran conflict on the U.S. economy, when the Fed will likely cut interest rates, why the market is still holding up despite all of the uncertainty, what is going to happen with tariffs and President Trump’s tax bill, where he sees opportunities in the market, and what he’s telling his clients right now.

Segment 2: Robert Sevim, President of the Chicago region of Savills, joins John Williams the outlook for the commercial real estate market in Chicago. What is the current state of the office leasing market? What’s the latest on return to office mandates? What can we expect from the market through the end of the year. Robert breaks it all down.

Segment 3: Kelly Clancy, Managing Partner, Lettuce Entertain You, joins John Williams to talk about the launch of Prime Meats by Lettuce!

Segment 1: Jason Turner, Chief Investment Strategist for Wintrust Wealth Management, joins John to talk about the fairly benign inflation numbers released this week, corporate earnings continuing to be healthy, and if he believes it’s time to lower interest rates.

Segment 2: Bree Fowler, Senior Writer, CNET, joins John Williams to talk about Tesla “tentatively” set to begin providing robotaxi service in Austin, Texas, later this month, and Disney and Universal suing popular artificial intelligence image-generator Midjourney.

Segment 3: Aki Ito, Chief Correspondent at Business Insider, joins John to talk about new data that shows that companies are hiring less in roles that AI can do.

Segment 4: Lisa Nucci, Chief Marketing Officer, Choose Chicago, joins John to talk about the launch of Choose Chicago’s new marketing campaign for the city,’ Never Done. Never Outdone.’

Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about long-term care insurance and what you need to know, what she thinks of President Trump’s plan to give newborns $1,000, and to answer all of your financial questions.

Steve Grzanich has the business news of the day with the Wintrust Business Minute.

United Airlines has partnered with Spotify to give flyers new in-flight entertainment. The partnership gives passengers free access to more than 450 hours of playlists, audiobooks and podcasts. The content will be available on United flights by 2026. United says it’s also working to allow passengers to sign into their own Spotify accounts. 

Also, 400 layoffs are being planned at CareerBuilder as the company prepares to close its U.S. headquarters in Chicago. Listen for more below:

Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk the importance of getting feedback at work, and why networking is key when trying to get a job

Segment 2: Philippe Weiss, President, Seyfarth at Work, joins John to explain why the most valuable employees of 2025 are ambassadors and anticipators.

Segment 3: Carl Prouty, “The Technologist” at Abt Electronics in Glenview, joins John to talk about some gift ideas for Father’s Day. Also, Carl tells John about Abt’s newest attraction: The Bear, a remarkably preserved skeleton of an 85,000-year-old cave bear! Customers can also make history by helping name the Cave Bear through a social media contest running from June 9–15, 2025. One lucky participant will win a $100 Abt Gift Card. For full details and to submit your entry, please visit Abt’s Instagram page @abtelectronics.

Steve Grzanich has the business news of the day with the Wintrust Business Minute.

Chicago-based Potbelly is seeing growth after warning in 2020 about going out of business. Crain’s says the sandwich chain has seen progress in its turnaround plan, including positive net income in the first quarter. Potbelly had income of $85,000 compared to a loss of $2.7 million during the same period in 2024. Sales rose about 1%. The company’s earnings beat estimates. Potbelly shares are up 20% in the last month. The sales jump comes as other restaurants have seen a drop.

Also, Bally’s casino has settled a lawsuit filed by an activist group. Listen for more below:

Segment 1: Ilyce Glink, owner of Think Glink Media and Best Money Moves, joins John Williams to talk about why Chicago is a great place for a staycation, and how low credit scores from student loan debt nonpayment has been impacting homebuying.

Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about a Chicago startup that helps disinfect spaces raising $1.6M, A new fund out of the University of Chicago will invest in deep-tech startups, and a Chicago-based investor in climate technology raising $430M.

Segment 3: Jodi Zombolo, Associate Vice President, Visitor Events and Programs, Chicago Botanic Garden, tells John everything you need to know about the new Patterned by Nature installation, which celebrates the universal attraction to patterns! Jodi gives us all the details on what you’ll see!

Segment 1: Craig Bolanos, Founder and Wealth Advisor at VestGen Wealth Partners, joins John Williams to talk about the good job report, what is driving the market today, the dustup between President Trump and Elon Musk, the outlook for Tesla (and EV’s in general) moving forward, the fantastic run that gold has had recently, what he thinks of Fed policy, why he think there should be two rate cuts this year, and the importance of keeping diversified.

Segment 2: Nick Schlanger, director of research services at NAI Hiffman, joins John to talk about why Chicago has an advantage over other regions for reshoring manufacturing.

Segment 3: Mike Spriggs, Head of Consumer Insights, Fiserv, joins John to break down the Chicago data in Fiserv’s May Small Business Index. You can look at the data via the AI assistant here.

Segment 1: Steven Esposito, President of Yellowstone Wealth Management in Lake Forest, joins John Williams to talk about the uncertainty in the market, but how uncertainty can lead to opportunity. Steven also explains why he believes its time for the Fed to cut interest rates.

Segment 2: Bree Fowler, Senior Writer, CNET, joins John Williams to talk about Meta cutting a 20-year deal to secure nuclear power to help meet surging demand for artificial intelligence and other computing needs, and the social media platform Reddit suing the artificial intelligence company Anthropic.

Segment 3: Matt Alston joins John Williams to talk about a recent piece he wrote in Business Insider about how employees dislike work satisfaction surveys.

Segment 4: Ray Stout, Executive Director, Illinois Craft Brewers Guild and the ICBG Educational Foundation, tells John everything you need to know about the return of Friday Night Flights to Gallagher Way in Wrigleyville.

Steve Grzanich has the business news of the day with the Wintrust Business Minute.

The University of Chicago has received a $21 million donation to establish a new quantum research center. Philanthropist Thea Berggren made the donation, and the new center will include her name. It’ll will be located in the Pritzker School of Molecular Engineering and will pursue research that merges quantum technology with biology.

Also, a new restaurant is about to open directly accessible from the 606 Trail in Chicago. Listen for more below: