
Matt O'Shea
Alderman of Chicago's 19th Ward since 2011 (City Council member), recently announced he will not seek reelection in 2027.
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Oct 30, 2026
Chicago school board election, new Bears stadium proposal | The Chicago Report
4:19
4:26
4:37
4:53
Anita BlantonHOST
Explain why you are so frustrated about this rollout and what you do know about this new pilot.

Matt O'SheaGUEST
So, you know, taking us back to the beginning, in September of 2024, more than two years ago, the mayor shut down ShotSpotter.

Matt O'SheaGUEST
When he made that announcement, he promised the city that there would be a replacement.

Matt O'SheaGUEST
There were nine bidders, and the Department of Procurement Services has had the names of those nine bidders and has had...
The Ray Stevens Show (Oct. 22, 2026) | Chicago’s Budget Crisis, Women’s Sports & Italian-American Heritage
17:27
17:47
17:57
Ray StevensHOST
How does this city, no matter who is the next mayor, or even if Johnson stays in there by some crazy chance, How do you work your way out of this mess that we've created?

Matt O'SheaGUEST
And if the election were tomorrow here in the city, two people are going to make that runoff.

Matt O'SheaGUEST
And I'm guessing a lot of your listeners are saying, what's this guy talking about? If the election were tomorrow, it's Brandon Johnson and Alexi Giannullis.
6 MINS LATER
Built to Win: a Deep Conversation with Dr. Chris Murphy & Dr. Matt O’Shea
7:35
8:00
8:08
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7:12Perrin DesPortesHOST
I wonder if you could maybe take us through some of the evolutions of your business and yourself as the entrepreneur and even talk about what might have been some of the biggest challenges along the way.

Matt O'SheaGUEST
Um, and I kind of was one of those guys who largely got into dentistry because that was, you know, all I really knew and just kind of was an easy path and wasn't entirely sure that that was me necessarily, but that's, that's the, the route that I took and, and early on was starting to burn out a little bit out sooner than I would have expected.

Matt O'SheaGUEST
Um, and then found spear education, which was my Kool-Aid flavor of choice, um, among many.

Matt O'SheaGUEST
Um, and I just went nuts on it and, um, had the time and the, the finances to make that happen.
23 MINS LATER
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30:59Perrin DesPortesHOST
Can you talk just a little bit about the way you think about fulfillment in life as a business owner and the way your business is a complement to that?
July 30, 2026 - 7 a.m.
31:56
32:08

Matt O'SheaGUEST
I'm going to the Cubs game, the Cards-Cubs game today with my girls and my wife, and we're going to have a blast this afternoon.

Matt O'SheaGUEST
Was there any doubt you were going to go into the family business? Tell me, after you graduated from SHU, were there stops along the way? Well, I made quite a few.
