Chicago’s Fab Five: The People Driving Our Entrepreneurship Community

With 16 years in Chicago’s entrepreneurship community, I have been as impressed and proud of our town’s recent surge of activity as anyone. A couple weeks ago, I got to thinking about what has driven it. What were the proverbial sparks that lit the fire? Who have the key players been?

A lot of people and organizations have made a difference. But as I pondered those questions, a handful came to mind rather quickly.

Here are the ones I consider to be Chicago’s Fab Five: the key players who have helped drive our community to where we are today, and who will inspire and guide us in the future.

  1. Groupon. No matter what is being said about its business model, sustainability prospects, IPO potential, or impact on small businesses, they belong on this list. A blog post I wrote for Crain’s late last year – especially the second half – explains why, so I won’t go into the reasons here. And no matter what happens with the company, they will remain on my list.
  2. Excelerate Labs. There are too many people involved to mention, but its founders – Troy Henikoff, Nick Rosa, Sam Yagan, Kapil Chaudhary – are the ones who obviously made it happen. Their ability to attract hundreds of applicants from around the country in the summer incubator’s first two years proved that entrepreneurs are willing to move to Chicago. Their ability to bring angels and venture capitalists from the coasts to listen to the companies’ investor pitches proved that there is indeed deal flow in Chicago. The fact that they invited a diverse cross-section of the community – not just entrepreneurs and investors but service providers, academics, technical experts, etc. – into the Excelerate Labs family proved that this effort isn’t just about them. And, most importantly, their ability to take fledgling startups with interesting business ideas and then mold them into high-potential business opportunities, proved that their effort is working.
  3. Matt With a vision, a few dollars, and an off-the-shelf social networking tool, the unassuming serial entrepreneur created what has become the place for Chicago’s digital community in the form of Built in Chicago. Matt has publicly acknowledged that he didn’t know what would come of it; he had no idea that nearly one year later, it would have 5,000 members and be a place to which where entrepreneurs, investors, and others in the community flocked for events, news, job openings, and chatter. He quietly secured modest financial support from some heavy hitters, invited the community to have a voice in its development, and continues to turn to BIC members for ideas and thoughts.
  4. Kevin Willer, Chicagoland Entrepreneurial Center. OK, I’m going to say what a lot of people have been thinking and whispering over the last few months: the new leader of the CEC is exactly what we needed. Kevin’s been on the job barely six months and has already had an impact simply because of who he is and how he carries himself. He puts his title, organization, and ego aside in the interest of the larger effort. He shows up at meetings and events, listens more than he speaks, greets people and spends time talking with them. His weekly blog and Twitter presence help create some transparency. All these things have helped turn the CEC into a more collaborative, accessible, and community-oriented organization than ever before; and in a mere six months.
  5. Ann Dwyer, Crain’s Chicago Business. This is one that might surprise some, but those of us who have been in the community for some time know what a difference-maker she has been. One challenge Chicago has had over the years is a lack of media coverage of entrepreneurial stories: the companies, founders, universities, organizations, and events. With the support of Crain’s leadership and her colleagues, Ann has quietly – and very effectively – brought those stories to light. She’s tapped into over a dozen people to contribute to her Crain’s blog for entrepreneurs (full disclosure: I’m one of them); has built an impressive following on Twitter due to her skilled curation of content and stories; and through that, has given a platform to hundreds of people and organizations in Chicago to tell the community what is going on.

As I said earlier, there are many more who deserve to be on this list…who’s your pick?

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