CEO Sundays: A Newcomer’s Thoughts On The Chicago Startup Scene

By February 27, 2011

Written by Nick Cronin

About five months ago I decided to quit my job and focus full-time on my startup ExpertBids I was living in Milwaukee, Wisconsin at the time, and although I loved the city, I wanted to move to a location with a more vibrant startup scene. Without my old job to hold me back, I was really open to move just about anywhere. My initial thought was that either of the coasts would be my best bet, but after doing some research I realized the startup scene in Chicago was really starting to grow. So last October, I moved myself and my business to Chicago.

Now fast forward to today and Chicago has not only met, but exceeded all of my expectations in terms what it offers to entrepreneurs and startups. In this article, I want to highlight three aspects of Chicago’s startup scene which I have found extremely helpful in running a startup. The list is not exhaustive and there are undoubtedly many other resources I have yet to uncover or merely forgot to mention.


There is no shortage of resources out there for entrepreneurs. BuiltinChicago is a great site to meet and connect with Chicago-area entrepreneurs and business people. The Chicagoland Entrepreneurial Center is worth checking out for the resources they offer. FlyoverGeeks, Technori, Beyond the Pedway and Enterprise City are all great blogs which cover area entrepreneurs, startups, and events.

One other resource I uncovered about a week ago was a program run by Sandbox Industries, which is called ‘office hours’. I thought it would probably be myself and one other person having a very short talk, but nonetheless I thought I’d give it a try. I was pleasantly surprised when seven people filled a conference room to talk with me about my business. For about an hour, I had the opportunity to talk with seven very intelligent and enthusiastic people, from technical to business people, who each offered a valuable perspective and suggestions regarding my business. At no-cost, this is a unique and fantastic resource for any entrepreneur in Chicago.


There is an ever-increasing number of events for Chicago area entrepreneurs and startups. Obviously, time is crucial when you are trying to build a company, but I have found that taking the time to attend some of these events is well worth it. I have found these helpful both in terms of there content and also the people I’ve met at these events (more on that below).

There is the bootstrappers breakfast where approximately thirty bootstrapping entrepreneurs get together and discuss the issues they are facing. I have found that discussing problems and solutions with other entrepreneurs in an informal setting can be very helpful both in terms of solving current problems and avoiding future problems.

Other events worth checking out are Entrepreneurs Unpluggd and Chicago Lean Startup Circle. Finally, though I have not yet attended, I look forward to MidVentures Launch and Groupon co-founder, Brad Keywell’s Chicago Ideas Week.


The people of Chicago’s startup scene have been the most impressive aspect to me. At each event I’ve attended, on the L, at my office, and everywhere else I go, there seems there is a real excitement about what is happening in Chicago. Fueled by Groupon and other wildly successful companies, there is a passionate community rallying around entrepreneurship and startups in Chicago. This is both exciting and motivating.

Not only is there passion, there is a real sense of community. People are willing and even reaching out to help startups and entrepreneurs in any respect they can. I have contacted and met with a lot of people and found the vast majority to be very helpful. I even unknowingly reached out to an advisor of a company which is in a way competitive to my startup. This individual was not annoyed in the least and politely told me he could not talk specifically about my business due to the conflict of interest, but told me he’d be happy to discuss any other topic. The reason I tell this story is that I think it encompasses the attitude of the people I have encountered and their overall willingness to discuss, introduce, and help out in any way they can. There is a passionate community out there who by helping each other out, are constantly improving the overall startup environment here in Chicago.

Because of this community and the other resources available, I am very happy, and proud, that I decided to move here to grow my business and be a small part of this exciting time for entrepreneurship and startups in Chicago.

Nick Cronin is the founder and CEO of ExpertBids, a professional services marketplace. ExpertBids is based in the Loop and allows individuals and businesses to get free, personalized bids from lawyers, accountants, and consultants. Prior to this, Nick was a practicing corporate attorney and founder of Nick lives in Old Town and looks forward to cheering for the Brewers in the heart of Cubs territory.