From Steel City to the Chicago Urban League with Karen Freeman-Wilson

Khullani Abdullahi (00:01.582) Hello and welcome to the AI in Chicago podcast. I'm your host, Khullani Abdullahi, the founder of TechniAI, a Chicago-based AI governance, risk compliance and strategy firm. AI in Chicago spotlights local operators, builders and thinkers, as well as policy and civic leaders who are scaling applied AI from their home in Illinois with a global impact. Each episode delivers practical stories and actionable insights. that empower leaders to understand AI and its implications and use cases, minus all of the hype. Our guest today is Karen Freeman-Wilson. and nationally recognized strategist whose career sits at the intersection of law, public service, and economic development. For over 40 years, Karen has been a driving force in navigating complex civic challenges. Currently, she serves as the president and CEO of the Chicago Urban League, where she leads one of the nation's premier civil rights organizations. In this role, she's focused on architecting structural change using data-driven programs to advance financial mobility and workforce readiness for Chicago's black communities. Her executive leadership is grounded in her tenure as a two-term mayor of Gary, Indiana. As one of the few Black women to lead a major American city, she spearheaded ambitious initiatives to modernize government operations, stabilize the local economy, and revitalize neglected neighborhoods. A graduate of Harvard University and Harvard Law School, Karen brings a rare mix of systemic economic analysis and on-the-ground community leadership. Most recently, she Khullani Abdullahi (01:43.616) she has turned her focus to the future of work, ensuring that as artificial intelligence reshapes labor markets, it continues to serve as a rule, as a tool of equity, rather than a driver of disparity. I'm so pleased to welcome a leader defining the future of inclusive economics, Ms. Karen Freeman-Wilson. Welcome. Karen Freeman-Wilson (02:04.798) Thank you so much, Kalani. It's so good to be with you today. Khullani Abdullahi (02:09.164) I'm so glad and I appreciate you taking the time to chat with me. I always like to start off with helping my audience understand. your origin story and where you've come from and how you evolved your civic leadership perspective. So I'd love to start off and invite you to tell us about your journey throughout your career and how you arrived at this point as a CEO of the Chicago Urban League and then think through and figure out when did AI first appear on your radar as a force that could appear on your radar as a force for meaningful impact or change in the community. easy serve. Karen Freeman-Wilson (02:51.818) That's really an interesting question. Well, I'm a native of Gary, Indiana. And if you know anything about Gary, it is the birthplace of US Steel. In fact, the largest for a long time, the largest corporation in the United States. It is still the home of the flagship operation. of U.S. Steel, which means that it is very much a manufacturing town. And so I grew up in that culture. My father was a steel worker. My grandfather was a steel worker. My uncles were steel workers and even my aunts worked in the steel mill. At the same time, my father and mother really instilled the importance of education and civic engagement in me very early on. Education was just a no thought given, that's just something that you had to do. Get good grades, you could do whatever you wanted to do, but you had to bring good grades into the house. Khullani Abdullahi (03:55.79) Right. Right. Karen Freeman-Wilson (04:18.474) And my mother was very community oriented. So she was involved with the NAACP. She was involved with the Urban League at that time. And she ran a building for one of the service organizations in the city, Gary Neighborhood Services. And so she knew a lot of people. At the same time, Mayor Richard Gordon Hatcher ran in 1967 for mayor. He was one of two people who were the first to run for mayor of major cities. The other one was Carl Stokes in Cleveland. They were both successful and the movement associated with their candidacy and service was something that very much influenced my life. I had the opportunity as a seven-year-old to see him campaign. In fact, he campaigned at a house party in the basement of our home. And throughout Mayor Hatch's 20 years of service, he always made himself available to young people. And so every time I saw him in the community, I would run and say, there's the mayor. And my mother's like, leave the mayor alone. He's busy. But because I had met him early on, that was my mayor just like it was everyone else's. Just as if I had really voted for him as a seven year old. But seeing that, seeing how he changed the community, seeing his Khullani Abdullahi (05:54.51) you Khullani Abdullahi (06:02.731) Right. Karen Freeman-Wilson (06:15.946) available and accessible way of service influenced my thinking about not only civic engagement, but public office, the importance of having people with integrity hold public office and very much influenced my decision early in life as a little kid that I wanted to do what he did. And And so I went about that business, maybe not as mayor early on, but certainly as a prosecutor, then a public defender, a judge, someone who brought drug courts to not just Gary, but the state of Indiana, and ultimately serving as AG and then being instrumental in the drug court movement nationally. But always with the I. and the idea of wanting to come back and serve as the mayor of my hometown. And it took three times, but I had an opportunity to do that. And once I did it for two terms, I knew that there would be always an opportunity or an effort on my part to do something in the service realm. And so that's the thread that has really influenced my life to be able to serve. And even now, as the CEO of the Chicago Urban League, the president and CEO, that is what we do every day. We serve the community here in Chicago. Khullani Abdullahi (08:05.71) Can you share a little bit about, and not everybody I think is familiar with the Chicago Urban League, can you share a little bit about the organization? I did a little bit of research and I hope I characterized it correctly when I was introducing you, but I'd love to hear directly from you, what is the Chicago Urban League and what does it mean and why is it important and why did it feel like the right next step for you in your civic leadership? Karen Freeman-Wilson (08:14.047) That's true. Karen Freeman-Wilson (08:35.731) Sure, so the Chicago Urban League is an organization that for almost 110 years will be 110 years old this December. We have promoted, fought for, advocated for economic and social justice for Black residents of Chicago and other underserved residents here in the community. And we've done it through a variety of measures. We've done it through advocacy. We've done that through the promotion of public policy, but we also have done it through direct programming. And so we have a workforce development program. We have housing and financial empowerment. We have entrepreneurship and economic development. We have youth and family services. We have a leadership practice that boasts one of the most prestigious leadership programs in the city of Chicago. And then we also have a research and policy institute that has published the state of black Chicago here in the community for over 60 years. Khullani Abdullahi (10:04.062) It's fascinating because I've run into two of the graduates of the leadership program before I even knew it was connected to the Chicago Urban League. Two of my previous guests and the first guest I ever had on this podcast, Tim Turner, who I believe is the president of the alumni association and then John James is also a graduate of impact. Karen Freeman-Wilson (10:11.591) Impact, yeah. Karen Freeman-Wilson (10:22.3) Of course, yeah, he's the president of the Alumni Association. Karen Freeman-Wilson (10:32.04) Yeah, yeah, absolutely. Khullani Abdullahi (10:33.198) All of the executive VP, C-suite Black leaders in Chicago apparently are coming through this impact program because everybody in AI and the senior level has somehow been connected to that universe. So I don't doubt the impact of that program. And you can see the leadership. in nonprofit, in finance, where Jean-James is. So I didn't know it was through the Chicago Urban League until many months after meeting both of them and interviewing them both. Thank you for sharing that. Karen Freeman-Wilson (11:07.114) Well, I call them all very affectionately, my children. They're still young enough to be my children in that the cutoff is 45. But yes, yes, for sure, for sure, yeah. Khullani Abdullahi (11:12.118) Yes! Khullani Abdullahi (11:18.062) 45 and they're both under 45 because I think I'm older than both of them and I'm 42. No, they've been very lovely and so thoughtful and I think so impactful. And so, you know, I think already there's individuals who are members of the Chicago Urban League broadly who are thinking about AI in different capacities as the leaders of a large one of the nation's largest civic organizations. How is AI entering the conversations and how did it get on your radar and where is it coming up most frequently and how are you guys thinking about AI as civic leaders? Karen Freeman-Wilson (12:04.564) Those are all great questions. It actually got on my radar before I came to the league. And it was from a policy perspective as people began to think about self-driving vehicles. And as a mayor, of course, you have to think about that from resident safety. Khullani Abdullahi (12:24.419) Right. Karen Freeman-Wilson (12:32.682) all kinds of things associated with the self-driving vehicles. And so when I got to the league, we had people who were already thinking about AI in both the training realm, the workforce training realm, in the entrepreneurship realm, and in our youth and family services realm as we Khullani Abdullahi (12:58.19) Right. Karen Freeman-Wilson (13:02.59) direct young people towards careers, we wanted to make sure that they understood and considered AI. And so we have been training in just the basics of AI so that people will understand the terms, so that people will understand what's possible, what the options are. And We've been doing that in our workforce training department for probably two to three years. We had a tech training program, a having tech training program, but we've also done it to help small business owners think about how AI can help in the advancement and forward movement. of their businesses. And so that is something that we do as a part of a business technology course for our entrepreneurs. And that's been extremely well received. But our real focus area is in the workforce development area. I was involved in Khullani Abdullahi (14:16.385) Yeah. Karen Freeman-Wilson (14:26.332) a jobs of the future study again during my tenure as mayor. And one of the things, and this was done with the African American Mayors Association. And one of the things that we wanted to really, really be intentional about as mayors is how do we ensure that our residents, our black residents in particular, don't get left behind? And so partnering with organizations like the League and others who do training like yours is so critical to ensuring that the wave that we see of artificial intelligence doesn't leave even more Black folks behind. I think, yeah, I'll leave it there. Khullani Abdullahi (15:00.92) Right. Karen Freeman-Wilson (15:23.284) for you to ask the next question rather than rambling on. Khullani Abdullahi (15:23.563) Yeah. No. So one of the things that strikes me is that you, as an elected official, had to deal with the regulatory aspect of AI first, right? Where can it be used? How can it be used? Where's the liability? Where are the risks? And so I think that gives you a risk-forward thinking, risk-based framework for it. So... Karen Freeman-Wilson (15:38.962) Sure. Yep. Yep. Karen Freeman-Wilson (15:52.724) Mm-hmm. Khullani Abdullahi (15:52.736) Alongside that kind of risk universe, where are you seeing some of the emerging opportunities and risks of AI for these communities of color? And alongside that question, do you think that the current civic leadership and elected officials and public policymakers, do you think they're equipped to lead? in an AI first world and what would they need to do to be able to be better positioned to lead? Karen Freeman-Wilson (16:29.448) I think that many of our elected leaders, civic officials have gone to great lengths to get as much information as they can. Even with that effort, they need more information. I think in order to lead effectively in this environment, because the information changes so quickly, because the technological advancements are so rapid, we need to Khullani Abdullahi (16:41.036) Yes. Khullani Abdullahi (16:57.56) Right. Karen Freeman-Wilson (16:58.854) almost have someone on the team that is not just an IT person. I mean, you know, every city has an IT person, but you really need someone who is in charge of advancement and technology. Khullani Abdullahi (17:15.884) Right. And then. Karen Freeman-Wilson (17:17.628) And so I think that's one of the challenges that elected officials have right now. Khullani Abdullahi (17:23.726) Right. So if you, as just as you're looking for your information diet, I always like to ask my guest questions that I think people can then turn around and act on. So say somebody was a part of your organization or a similar organization, what should they be sharing with their leadership and in what format? to help inform your strategies and choices and the data that you have access to. Karen Freeman-Wilson (17:55.036) I think that one of the things that we would like to know more about and that we're really looking for more is what are some of the entry level opportunities for AI? What are some of the barriers that are created through AI? How do you... Khullani Abdullahi (18:12.846) Okay. Wait. Khullani Abdullahi (18:18.094) Right. Karen Freeman-Wilson (18:23.654) address those barriers so that people are not hampered from a job opportunity standpoint. How do you get people to rethink their job opportunities? For instance, at one point, Khullani Abdullahi (18:36.376) Right. Karen Freeman-Wilson (18:48.094) there was a movement for people to either go to the workforce or the military after graduating from high school. And then there was a movement to say, everybody should go to college. You can go to junior college, you can go to four year college, you can go to, but you gotta go to college because that's how you get, education is the key. Now, people understand that you don't necessarily need a traditional college degree, two or four year, in order to have a meaningful career. And so I think that it is really important and possible for the discussion around AI to really frame the Khullani Abdullahi (19:22.478) Right. Karen Freeman-Wilson (19:41.02) opportunities that exist to have meaningful careers without spending two full years or four full years in an educational setting. So what does that education look like? When do you start the exposure? How often, you know, do you need to be updated? And, you know, for instance, We do CLEs all the time as attorneys, but do you need it? What does that look like in the AI universe? So those are the types of things. And so that's from the hands-on, practical workforce side of it. But there's also the public policy side of it that says, well, AI for everything. Well, if you say that. Khullani Abdullahi (20:11.821) Yes. Khullani Abdullahi (20:16.43) Right. Karen Freeman-Wilson (20:37.277) then that's going to have an impact and in many instances, a negative impact on the ability of people to get employed. So what does that mean? You don't just stop AI, because we know that it's not stopping anyway, right? So how do you get people retooled for other areas? How do you... accelerate their AI education so that they can get retooled for even something that is more of a long-term career opportunity in the AI arena. Khullani Abdullahi (21:18.414) Excellent. So do you think Chicago, Chicago we know it has, is pretty, I think the city of Chicago is like 30 % African American, 30 % Latino, 30 % white American. And so it is one of the more diverse cities in the country, kind of evenly split, but still pretty highly segregated. What does a equitable economic empowerment in AI-driven economy look like in Chicago with all of its class and race issues? And what is it about Chicago that enables it to be able to kind of solve these problems in ways that probably other cities may not be able to? Karen Freeman-Wilson (22:08.68) I think that the first thing that allows Chicago to solve its challenges around not just race, but around race and poverty is the recognition that it has a problem. You know, there are other communities, regions that live under the guise Khullani Abdullahi (22:22.008) Mm-hmm. Khullani Abdullahi (22:26.402) Right. Karen Freeman-Wilson (22:36.106) of being fully integrated and that everybody has an opportunity to do everything. Chicago knows that's not the case. We see it every day. And increasingly, people understand the relationship between allowing the status quo to fester and Khullani Abdullahi (23:02.924) Right. Karen Freeman-Wilson (23:05.04) and what happens to all of us. So we understand that unless I ensure that people on the South and West sides have options and opportunities to work in the AI field, their inability to realize those opportunities will adversely impact me on the North side. That's just... Khullani Abdullahi (23:33.165) Right. Karen Freeman-Wilson (23:35.026) real. So if that's the case, then I should be even more committed to creating a level playing field both in and out of the AI arena. and you can't talk about the creation of that level playing field without really thinking about what type of education people receive because you have to have a certain baseline education to really understand and act in the AI universe. Khullani Abdullahi (24:18.35) right? The fundamentals almost. So from where you Karen Freeman-Wilson (24:21.778) Yeah, well you gotta have it. Khullani Abdullahi (24:24.0) Yeah, from where you sit kind of at the intersection of economic development, public policy, civic engagement, marginalized communities, and then also in the third largest city in America, if you had to kind of prioritize gaps in access or training or readiness, and you could wave a wand and issue some new policy or corporate action that would immediately reduce the risk of What would it look like for you to choose a policy or a corporate action that you think would have an immediate impact? Karen Freeman-Wilson (25:05.83) Absolutely, and that's a great question. I've been working with the Civic Committee of the Commercial Club, and that's the committee that really promotes civic engagement. And the corporations that are members of the Commercial Club have really been tasked to look at their employment. opportunities to look at their workforces and determine, you know, what are those jobs that really don't require a college degree? And how do you develop a training program for those jobs? What does that look like? And how can you work with groups like the Urban League, like Skills for Chicago Lands Future, like the CARA Collective to say, we're going to train you, we're going to spend 10 to 12 weeks training you in this opportunity so that you can go right into the workforce, support your family and create better opportunities, not for yourself, not just for yourself, but also for your children. So that is not necessarily a mandate that you can place on corporations, but what we've tried to do is place an imperative on them to say, if you do this, not only will it be better for the people who will be the recipients of these opportunities, but it'll be better for you and the others in your company who believe themselves to be far removed from the issue. Khullani Abdullahi (26:35.491) Right. Khullani Abdullahi (26:53.544) Right, these communities. And I think that's such a clear action because there are so many jobs I and I can speak for. We've all held jobs that no one taught me how to do in college or law school, right? There's the work of being in the real world. In fact, when you show up, Karen Freeman-Wilson (27:10.218) Yeah, yeah, of course. Khullani Abdullahi (27:16.394) everybody goes through an informal or formal training process and apprenticeship in the real world because in the real world, you know, even if you do internships, there's a disconnect between your education and business requirements. So making that explicit and saying, you know, if there is not a college degree required for someone to show up and you're going to have to show them how to do this work anyway. then why make it a barrier to entry to joining your organization? Okay, so on the corporate side, I think that's a very clear, like a corporate action that they can take that can address these risks. Karen Freeman-Wilson (27:43.572) Yep. Khullani Abdullahi (27:58.39) What policy recommendations do you have when it comes to reducing the risk of inequality in the AI arena? What are some things that policy leaders can do? And in the spirit of full transparency, I interviewed Representative Bob Morgan. in the past who's the architect of the AI and mental health bill. So I know there are policy and elected officials in Illinois who are willing to act on AI. So I don't think it's far-fetched to share with them some of the policy recommendations you have from where you sit in our city. Karen Freeman-Wilson (28:18.836) Sure. Karen Freeman-Wilson (28:34.356) So I think that one of the things that we have to be careful for about, and we know about minor aspects of, and I won't say minor, but we know about aspects of AI, like when you put your hand under the faucet, it might detect it, but it might not. So a person like me has to go like that, right? Khullani Abdullahi (28:52.749) Yes. And it does not recognize you. Yeah. Right. multiple times, yep. Karen Freeman-Wilson (29:04.074) So that's a minor, you know, it's a nuisance, but it's not going to change my life. There are other aspects of AI that could be life changing. And so I think there is a level of vigilance that elected officials have to have that. Khullani Abdullahi (29:15.018) Right. Khullani Abdullahi (29:18.434) Mm-hmm. Mm-hmm. Karen Freeman-Wilson (29:31.914) community members have to have, that those who are civic leaders, whether you're talking about sororities and fraternities, whether you're talking about other civic groups, have to think about that historically they have not necessarily been tasked to think about. That, you know, they might say... They might believe that to be out of their will, will house, but I'm suggesting that it is not and that we need everyday people to understand it so that they can talk to the legislators of Illinois so that they can advocate to the Cook County Board, to the mayor's office, to others who. really do care about this and who may not have even thought about. Khullani Abdullahi (30:32.174) Right. That's excellent because I think it just don't opt out, right? You have to opt in. Don't opt out and say, yeah. Karen Freeman-Wilson (30:38.952) Yes, yes. You have to opt in. Because it's easy to your point to just opt out and say, you know what, that's not my area of expertise. And I'll tell you a secret, that was probably my first inclination. Khullani Abdullahi (30:58.06) Right. Karen Freeman-Wilson (30:59.56) But then when I realized that this is not going anywhere and there is opportunity in this space, then I said, know, okay, it's time for you to understand. Now, G.P.T. is my friend. Khullani Abdullahi (31:16.47) Right. You don't know how you lived without it, right? Aren't you glad? Aren't you glad? I do think that we were lucky that we had access to these technologies after college and law school though, because could you imagine not doing your own outliers? Karen Freeman-Wilson (31:23.754) I don't know. Yeah, right, right, right, right. Karen Freeman-Wilson (31:34.637) gosh, it would be a dilemma. It would be a dilemma. Khullani Abdullahi (31:38.318) You had to those outlines, right? Now it does them for you. I tried and I looked, do all your entire constitutional law one outline in 30 seconds, which took us four months in the library. One case. Karen Freeman-Wilson (31:50.73) Sure, that would have cut into my hustle because my roommate and I used to sell outlines. That would have taken my whole reverence new stream away. Khullani Abdullahi (31:58.382) That was a whole revenue stream back in the day. Khullani Abdullahi (32:06.35) that's too funny. And I suspect you would not be the accomplished attorney and civic leader you are today if you didn't have to create any of those. It is, I think it is a double edged sword, right? The tool. Karen Freeman-Wilson (32:08.786) Yeah. Karen Freeman-Wilson (32:16.252) Hey, I'm telling you, I'm telling you. Khullani Abdullahi (32:23.82) you know, using the tool to expand your own bandwidth and capacity or having the tool reduce your cognitive capabilities, right? And I think about that a lot with, I have a seven year olds and how we think about AI and parenting. So there's a lot there. Karen Freeman-Wilson (32:29.673) Yes. Karen Freeman-Wilson (32:35.945) Yeah. Khullani Abdullahi (32:40.814) I think something that you shared that I thought was really compelling is this notion of not excluding yourself prematurely. Are there any recommendations you have for helping people shift from a fear of automation to a feeling of... agency and opportunity, right? What can you say to people who are ignoring the AI emails that they're getting from their teams, who are not signing up for the tools, who think they can just ignore it the way they've ignored other digital transformations? What words of wisdom and feedback do you have to help them kind of make that shift? Karen Freeman-Wilson (33:29.04) I always use something that is really, really simple. Two things, one is I remind them, or at least some of them, of a time when people didn't use seat belts. And now you wouldn't leave home without one. The other thing is that I challenged them. I said, you know, you don't have to read a peer-reviewed treatise, but just read one page about AI. And you always remind them you're using it anyway. Khullani Abdullahi (34:02.221) Right. Right. Khullani Abdullahi (34:12.94) Right. Karen Freeman-Wilson (34:13.736) You're always asking Siri something. You're always asking Google whatever the Google's name is. You're always asking them something. So why not let it serve you even more? Other than to find, you know, how to shaft. I just aged myself. Khullani Abdullahi (34:16.823) Do we have? Khullani Abdullahi (34:24.823) Right. Khullani Abdullahi (34:29.518) All right. Khullani Abdullahi (34:34.818) Right. Khullani Abdullahi (34:41.406) You did because I was thinking I was like the car part like the shaft Jackson it is Samuel Jackson Okay, the other part is I need to speak English to like 98 99 so I missed a lot of pop culture Karen Freeman-Wilson (34:44.794) It's like, Shannon, who is Shaft? Who's Shaft? John Shaft. Karen Freeman-Wilson (35:00.026) Okay, yeah, so you miss you miss John Shaft. He was long gone, but his grandsons came back. His son and grandson came back. Khullani Abdullahi (35:09.14) I have to look at that. When you have heard from citizens and everyday people, in addition to AI maybe impacting their jobs, have you heard of other categories of concerns that they've raised around AI? Karen Freeman-Wilson (35:11.368) Yeah. Karen Freeman-Wilson (35:20.286) Mm-hmm. Karen Freeman-Wilson (35:28.062) Certainly the safety concern, the displacement, like you said, people often talk about it making them lazy or making their children lazy or dumb. And, you know, not using it pejoratively, but just making people lazy. Khullani Abdullahi (35:33.773) Yep. Khullani Abdullahi (35:45.032) Mm. Right. Khullani Abdullahi (35:53.578) Right. Impact it has on the young people. So when we think about community, so one of the, think, like, Karen Freeman-Wilson (35:55.112) Yep. Yes, for sure. Khullani Abdullahi (36:04.606) and this is true for I think almost all communities across the board, is that there is a big distinction between the companies building the AI technologies and deploying them in communities and then the citizens who have to live in a world where these technologies exist. Now we know in Europe, Karen Freeman-Wilson (36:23.498) For sure. Khullani Abdullahi (36:24.714) we have, they have very strong articulation about community harms. And then they have strong protections against those community and citizenship harms that they've identified. And so for example, in Europe, your grocery store, can't do a retina scan and a facial scan and connect your mobile data to your purchasing data and have this profile of what shelf you looked at and then what chips you ended up buying, right? That is not the Karen Freeman-Wilson (36:54.014) Bye. Khullani Abdullahi (36:54.628) case in America. when you and so Illinois, unfortunately, we live in a state where I think we're very comfortable, you know, regulating. But having said that, as we think about community harms and harms to citizens, like in addition to concerns about bias or surveillance, et cetera, Karen Freeman-Wilson (36:57.011) no. Yeah. Karen Freeman-Wilson (37:01.098) you Khullani Abdullahi (37:17.614) how over the last 40 years of your career, you've seen different harms come and you've seen governments and elected officials come up with different kinds of safeguards. What do you think are the kinds of safeguards and strategies and risk mitigation for harms for communities that we can maybe think about applying in this AI world that you have seen succeed in the past? or that you've seen implemented in communities, what might governance or safeguards look like for protecting people in the AI world? Karen Freeman-Wilson (37:52.938) So I think we have to look at how information that is collected, whether it is scans, retina scans, finger scans, any of that information that typically is collected through jobs or sometimes just through convenience. mean, think Amazon, right? When you go to Whole Foods. I think we have to regulate access to that information and how it's used. You know, the same may be thought about or regulated as well as you think about the AI that's used through ring doorbells and other electronic monitoring items, license plate readers, things of that nature, you have to... really think carefully about how those tools are used and how you monitor people. And so the General Assembly really does have to think about in advance, how might they be used, but more importantly, how might they be abused? Khullani Abdullahi (39:17.198) What do you say to corporations, and we know this happened when Illinois passed the Wellness and Oversight of Psychological Resources Act in August of 2024, 2025, I believe. companies lobbied and said, if you regulate AI and chat bots, it's going to impact innovation, don't kill innovation. What do you say to companies and groups that are going to want to resist the regulation and collection of biometric data and the way that we use that data, especially in AI world? What pushback would you have to their claims of you're going to reduce innovation? Karen Freeman-Wilson (39:58.314) would say that that's not true. I mean, you look at other things that have been developed over time, whether you're talking about alcohol, whether you're talking about vehicles, everybody can't drive a vehicle. You know, we regulate that. We are a society that regulates things and regulates innovations for the protection. Khullani Abdullahi (40:02.946) Yeah. Khullani Abdullahi (40:12.866) Mm-hmm. Right. Karen Freeman-Wilson (40:26.566) of those who need it the most. We're able to walk and chew gum. And so that's what I would say. Khullani Abdullahi (40:31.566) Right. Regulation does not preclude innovation. I love that. tell me about your 2026 vision for the Chicago Urban League, particularly as it relates to AI. Karen Freeman-Wilson (40:39.12) at all. Khullani Abdullahi (40:52.758) What does the ideal strategy and vision that you guys have laid out look like and your efforts that are coming up in the next 12 months? Karen Freeman-Wilson (41:04.092) So there are two areas that I think are really important to this conversation. The first is our overall pursuit of a democracy agenda. And by that I mean advocacy, mean the use of public policy or the pursuit of support for public policy. And I also mean the importance of civic engagement, how we encourage people to be civically engaged. Voting is just the baseline, but there are other areas and ways to be civically engaged. And much of that will intersect with the way that we think about artificial intelligence. The other... thing that I'm excited about is very practical. And it's kind of something that plays to our hands-on programming versus our public policy work as well. And that is the utilization of or the implementation of training programs that will allow people to go right into a job. and utilize AI skills and build on them through the training that's available at that job. And if we can make them prepare people for the entry level utilization of artificial intelligence, then they get in and the sky becomes the limit for them. Khullani Abdullahi (42:47.213) Right. Khullani Abdullahi (42:55.052) Right, for those individuals. If you could share, are there any corporate partnerships or sponsorships, et cetera, that would be helpful in 2026. What kinds of organizations would you be looking to partner with and in what ways? Karen Freeman-Wilson (43:14.418) Yeah, so I would say our tech companies getting support from our tech companies and we certainly have a relationship with Google currently. We're looking to grow that and have been in talks with them. We would love to enhance our relationship with Microsoft. We think that that is critical to our training efforts. Khullani Abdullahi (43:26.99) Right. Karen Freeman-Wilson (43:44.122) And then some of the other platforms that people don't, you you don't think about Uber as a tech company, right? You think of Uber as a car company or transportation. It's all about tech. DoorDash, tech. Instacart, tech. You know, all of those are Airbnb, tech. They utilize tech to make life easier. And so, You know, one of the things that I'd like to do with our youth is kind of put that, those origin stories in front of them, right? To help them think about how did someone go from this idea to having the biggest tech company in the world, like an Amazon, like some of the others. And if we can do that, then we'll see our next generation of tech companies, many of those may even come from our community. Khullani Abdullahi (44:55.19) I think that's such a great point because Chicago in general, have a very diversified economy, but we haven't done a great job in building large native homegrown technology companies that are founded and built here and that are, you know, where all the fundraising happens and all the growth happens. And I think that that is a very large missed opportunity because it only takes few unicorns to transform a city and an economy, right? And so I love that. Okay, so when you look at the years ahead, I'd like you to share kind of, you know, the thing that keeps you up at night. What are some of the questions that keep you up at night about Chicago's potential in the age of AI? And then also, what gives you hope? about Chicago's potential in the age of AI over the next few years. Karen Freeman-Wilson (46:00.702) Well, certainly one of the things that keeps me up is the fact that some of our colleagues, some of our children could be left behind if there aren't equitable opportunities. That keeps me up to the point that we are always thinking about how do we prevent that from happening? How do we work in coalition? Khullani Abdullahi (46:16.844) Right. Karen Freeman-Wilson (46:28.756) to prevent that from happening because that's not just an urban league move. At the same time, the thing that makes me hopeful is that we're not the only one thinking about this. We're not the only one that cares about this. We're not the only ones who are committed to this work. And because we're not, then that... bodes well for the opportunities that we can provide to our next generation. Khullani Abdullahi (47:06.7) Well said. I usually like to wrap up my interviews with some lightning round cultural questions. So I'm with all of them, but I'd love for you, before we dive into your final thoughts, is there a favorite neighborhood restaurant or coffee shop that you enjoy, that you would recommend? Karen Freeman-Wilson (47:14.986) Love those. Karen Freeman-Wilson (47:32.114) I love Virtue and Hyatt Park. Can't get enough of it. Khullani Abdullahi (47:34.55) Okay, can't get enough of it. Virtue in Hyde Park. And then deep dish or flat, is it flat fried pizza? thin crust. Thin crust? Okay. Karen Freeman-Wilson (47:37.5) Yeah. Yes. Karen Freeman-Wilson (47:43.69) thin. I'm a thin crust person. That comes from my East Coast days. Khullani Abdullahi (47:49.63) Okay, okay. And then it doesn't have to be a Chicago leader, but is there a leader, past or present who inspires your approach? Karen Freeman-Wilson (48:00.656) I have always been inspired by Barbara Jordan. I think that she is practical. She is one of the most inspiring communicators I've ever seen. It would have to be Barbara Jordan. Khullani Abdullahi (48:18.36) Can you tell me who she is? I feel like I should know, but I don't. Karen Freeman-Wilson (48:21.386) No, sure. Congress person from Texas was one of the prosecutors of Nixon in the Watergate case. So a little bit before your time in the 70s. So yeah, that's not a bad question to ask. But yeah, if you look up her cross-examination on YouTube, it is... Khullani Abdullahi (48:25.889) Okay. Khullani Abdullahi (48:31.928) Yeah. I'll have to. I'll have to look her up. Karen Freeman-Wilson (48:49.514) still mesmerizing. Yeah, yeah. Khullani Abdullahi (48:50.104) The master class. Wow, okay. Thank you. I have learned something new. Okay, and then is there a book, speech or idea that you return to often? Karen Freeman-Wilson (49:05.994) That's a, I would have to say to whom much is given, much is required, reference the Bible. Khullani Abdullahi (49:14.838) Yeah. Any final thoughts that you'd like to share with our audience on anything that we've discussed? Karen Freeman-Wilson (49:24.516) I, one, I just want to thank you for creating this space. It's so important that people understand that AI is something that we should embrace and not be afraid of. I know that there is this continuing debate about technology, whether you're talking about AI or data centers or, you know, there's just this great apprehension. I mean, this palpable collective anxiety and I'm just encouraging people to look for the opportunity in those spaces because one recognition that we should all have is that it is here to stay. Khullani Abdullahi (50:12.118) Absolutely. Karen, thank you so much for taking the time. I really appreciate you. And I appreciate all the insights that you've shared. I imagine that our audience will have a lot to think about. And hopefully, you've given other leaders frameworks and strategies and thoughts that they can bring into their own work. So thank you so much again. Karen Freeman-Wilson (50:18.548) Thank you. Karen Freeman-Wilson (50:35.198) Thank you, Kalani. It's been an honor to be with you and on your program. Khullani Abdullahi (50:41.258) should think.