From October 14 to 20, nearly 200 thought leaders from around the nation—including Dr. Buzz Aldrin, Cat Cora, and David Gregory—will be on hand to speak at Chicago Ideas Week, which entrepreneur Brad Keywell established in 2011 to foster ideas and collaboration to ignite change. Beyond the weeklong event, though, CIW boasts a co-op of members eager to help Chicago make moves globally. In a lively recent discussion at the Ideas Week offices, Michigan Avenue Editor-in-Chief J.P. Anderson joined Keywell, CIW Executive Director Jessica Malkin, and other key supporters of the event to discuss how Chicago Ideas Week is fulfilling its mission to help the city think forward.

See profiles on eight of the movers, shakers, and thinkers involved with Chicago Ideas Week>>

Michigan Avenue: Let’s start from the beginning. What was the inspiration behind Chicago Ideas Week?
Brad Keywell: I happen to love ideas. I’d gone to a number of different “ideas things” like the Renaissance Weekend in South Carolina and the Aspen Ideas Festival. When you’re at these conferences, there’s an energy that is created out of nothing and connects you, which results in activity after the conference that wouldn’t happen otherwise. I was envious of that. Especially on the West Coast, they have a lot of stuff that connects people inorganically—engineers with poets, or scientists with technologists—so the idea was to do this here in Chicago. Motivator number one was that we didn’t have it; number two was people saying it would never work. My response was, “Great, let’s just do it.” And off we went. I went around and told the story about what we were going to create, and every entity and organization that we spoke to about it responded by saying, “Amen. How can I help? How do I get involved?” That first year was so significant. Jessica Malkin and Carrie Kennedy and the team that came together—the level of performance was so high that we hit a grand slam out of the gates, and all of a sudden it was real.
Jessica Malkin: Year one was like a Brad Keywell road show through Chicago trying to tell everybody in our networks what was going to happen, and we pulled it off. So we took the next challenge from Brad, which was to grow it. This year, it’s become more about creating a year-round community [and becoming a] connection warehouse that people can utilize to start to “mind-mob” issues—which is Jimmy Odom’s term—so we can help tackle some of the issues that the city’s dealing with.

MA: What drew the rest of you to become participants in Ideas Week?
Imran Khan: I started teaching at William R. Harper High School, which is considered one of the toughest schools in the country. I began to realize there was a huge gap in social and cultural understanding and connectivity, and it’s hard to describe the impact of that isolation—how dramatic an effect that has on the future of our city and of so many people’s lives and their understanding of what is possible. I was teaching kids who had never been in elevators, never seen the lake, never been to grocery stores. I started to really attack the problem with a couple of teachers [to expose kids to experiences in the city]. When we met everyone at Chicago Ideas Week, we were on the same wavelength: We combined our ideas and started serving about 25 kids in a single school; now, we’re serving 360 kids in six schools. Teachers do great work, but Ideas Week gave us the platform where we can have the megaphone, we can tell the story, and things blew up.
Patricia Cox: I was looking for inspiration and information around the things that mattered to me: urban issues, education, healthcare, culture, and interacting with the community in a meaningful way. I looked at the first lineup of Chicago Ideas Week, and I was like, “Check! Check! Check!” Every issue was being explored in multiple dimensions, which was important. I was also starting to invest in small companies—Impact Engine, Accelerator, 1871—and felt like CIW hit on all the things I was thinking about in a way that expanded it. I wanted to be part of it and see if I could help build it in some way.
Leslie Bluhm: Also, the way that Brad created it is much more accessible to people than your typical ideas conference. A lot of them are unbelievable events, but because of location and cost, they’re not accessible to everybody. One of the beauties of Chicago Ideas Week is it’s absolutely accessible.

MA: To the casual observer, there may not necessarily be an awareness of Ideas Week’s mission to effect social change. How did that aspect of CIW come about?
JM: After [we proved ourselves in] year one, we sat down with key partners and they challenged us to choose one issue to tackle. We were coming off a summer that had extreme levels of violence. We [decided on] an initiative around how to get guns off the streets, and we did an official partnership with the City of Chicago and Twitter, [asking the question “What if Chicago got illegal guns off its streets?]. It was the first time any campaign had been done with a tri-partnership like that. We went from nobody really realizing what the platform was and that it existed to a half a billion media impressions worth of exposure. The city of Philadelphia ended up creating the Philly Peace Plan, a campaign in reaction to What If Chicago, launched just two days after we launched. Now we’re talking about [a larger-scale] phase two of the gun initiative.

MA: It’s unique that CIW is a private venture, and yet you’re working hand in hand with the public sector to make things happen. How does that dynamic work?
Jimmy Odom:
To me that’s how it should be. It’s so strange that we think we should simply elect officials and say, “Hey, you have great ideas: Go, step back, and watch this develop.” What could we expect to happen other than us being disappointed with what they come back with? But, if we have a collective group of intelligent, motivated individuals who come together and say, “Not only have we elected officials, but we’re going to come up with ideas, think outside the box, and not be restricted because we have no chains,” real solutions can be presented much more efficiently. We should not be detached from solutions.
JM: This city has no lack of people hounding them with great ideas about how to make everything better, not realizing the restrictions that exist; instead, what we look to do is say, “What are the areas in which you need our help?”
BK: If we had started [CIW] with an agenda—if there had been any politics or partisanship or whatever, none of which I have any interest in being part of—CIW wouldn’t be what it is. By virtue of it being a 501(c)(3)... it’s hard to take issue with the quality of discourse that comes out of what we’re doing.
Mike McGee: The Starter League has been working with the city and the mayor specifically to show teachers web development so they can educate their kids how to code. One of the things that the mayor can’t do is teach people web development. We can do that. But, he has the connections with Chicago Public Schools to make that happen. It’s not about putting everything on someone’s shoulders, but it’s recognizing the strengths of both sides. That’s a true partnership.
BK: Can I ask you a question, Hebru? How do you think this city helps its artists?
Hebru Brantley: There’s a huge lack of help with artists, down to the core of the CPS. There were several programs for schools that would integrate the arts more, but it comes back to the level of experience that some of these kids have outside of that four-block radius. It’s hard to teach a kid about Basquiat or Warhol if they’ve never set foot in a museum before. The impact from a jpeg to an actual piece is completely different. Putting a computer in front of a kid doesn’t make him or her a graphic designer. Giving them pencils doesn’t make them artists. They need to be guided and coached just as they would in a math or science class.

MA: To Brad’s point about how the city encourages artists, how do all of you feel the city encourages innovation and new ideas?
JO: [My company] WeDeliver is a by-product of the support of Chicago, our business leaders, our social representatives, and our political system. I am a living, breathing example of how the Chicago ecosystem began to foster innovation.... There’s technology being built that’s supporting the system that we have. It’s created a snowball effect. Truly, Chicago has become a part of that conversation. Our Groupons and our Grubhubs put us on the map, but that was simply a blip. Now there’s so much more around us allowing Chicago Ideas Week to amplify what’s already happened.
MM: Brad was talking about how he started Chicago Ideas Week through storytelling: All he had was a story to tell, and he just went around Chicago. That’s the same way that we got started with The Starter League. We didn’t have any money, but we had a story about what we wanted: We wanted to create an environment where people without the skills to build start-ups would have a safe and fun place where they could do that. We went around to as many people as we could find, and they said, “How can we help?” One thing that is beautiful about this city is that there are amazing people here who are willing to help.
BK: The one issue we still have in Chicago is that we’re not comfortable with risk and failure. We punish failure, and that’s dangerous. What marks the Silicon Valley community as being so awesome is that when you fail, they’re like, “Okay, what are you going to do next?” We’ve got to change the general appetite for what a “good” fail means—and once you fail, do you deserve a second chance? I think you do.
LB: The social entrepreneurs we bring as fellows to Ideas Week report that one of the most important things they get out of the experience is this fellowship. They need a community whether they have success or failure, and that absolutely is what Chicago Ideas Week does for them.

MA: Let’s think about Ideas Week 2018: What do you envision in a best-case scenario that Ideas Week will be doing?
There’s stuff going on year-round, and Ideas Week is the Super Bowl of a year’s worth of activity. It’s acknowledged on a global basis as one of the important ideas platforms that exists; the co-op has morphed into a series of platforms where serendipity is created and communities activated in lots of creative ways.... I can keep going! The good news is we’re going into our third year, and it’s already one of the important ideas platforms in the world. It took Davos 20 to 30 years. Five years from now is a long time.
MM: At our last co-op meeting, someone brought up the point, “How is Chicago known outside of Chicago?” We know all the amazing things that we do, but there’s this perception out there about the city’s identity that we don’t think about every day. It would be great in three, five, 10, 15 years if Chicago is the place where innovation happens, education happens—like a mecca. The thing that I hear a lot in our community is we need to be more like Silicon Valley or New York. But I want us to do it our way.
HB: This is my first year with CIW, and I feel rejuvenated. I’ve been in conversations before like this with different people, but I never felt—once I left the table—that anything would come to fruition. Listening to everyone talk here, it’s put a battery in my back to go the extra step because I feel like my efforts will be matched.
BK: We will match your efforts. I promise.

See the extended version of our Chicago Ideas Week interview here>>

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