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Matt O'Shea

Matt O'Shea

Alderman of Chicago's 19th Ward since 2011 (City Council member), recently announced he will not seek reelection in 2027.

Oct 30, 2026

4:19
Explain why you are so frustrated about this rollout and what you do know about this new pilot.
4:26
So, you know, taking us back to the beginning, in September of 2024, more than two years ago, the mayor shut down ShotSpotter.
4:37
When he made that announcement, he promised the city that there would be a replacement.
4:43
So for the past two years, we've waited for what that replacement could be.
4:49
There was a request for proposal, an RFP put out.
4:53
There were nine bidders, and the Department of Procurement Services has had the names of those nine bidders and has had...
5:05
many to choose from for over a year.
8:20
Why do you think we can't get past that?
17:27
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?
17:38
Well, you know, it's the problem we see here in our city.
17:40
It's the problem we see everywhere.
17:42
People won't come to the table and look to find middle ground.
17:47
And if the election were tomorrow here in the city, two people are going to make that runoff.
17:52
If the election were tomorrow, it's Alexi Giannoulis versus Brandon Johnson.
17:57
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

23:59
Can you expand on that?
7:12
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.
7:27
Sure.
7:28
Um, yeah, just to, to put a little bit of context on it.
7:32
Um, like I said, my dad was a dentist.
7:35
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.
8:00
Um, and then found spear education, which was my Kool-Aid flavor of choice, um, among many.
8:08
Um, and I just went nuts on it and, um, had the time and the, the finances to make that happen.

23 MINS LATER

30:59
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?
31:52
Tell me about that.
31:53
They love them.
31:55
They love them a lot.
31:56
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.
32:03
But dad and mom definitely loving having the grandkids around.
32:08
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.
32:16
Bradley, Illinois Central College, Lincoln Land, and finished up at UIS.
34:38
No,

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