A Short Thought About the Chicago Startup Community

Last night I was invited to speak at WeWork on Kinzie in Chicago for Startup Grind.  It was a lot of fun.  The presentation was from 7-8, I got there at 6.  I was there speaking with entrepreneurs until 10:30.  I walked home and fell into bed around 11. The room was full.  The people were engaging and working on very interesting things.  There were people from all walks of life, all genders, all colors.

Chicagoans tend to walk with a bit of a chip on our shoulder.  We bristle when people say we aren’t good enough.  It comes from our history as the Second City.  The cover of the New Yorker sums it up for us.

We live in flyover country. People flock here from flyover country because in the greater Midwest, Chicago is truly the only metropolis that approaches an urban city like New York or something from Europe.

The Ivy League gets all the press.  But, the Big 10 is a damn good place to go to school and plenty of Big 10 alums left and built the cutting edge technology every one drools over in the Valley.

I think it’s time to stop wondering if Chicago has a startup community or not.  It does.  If we continue to nurture it, it will get really big.  It is wrong headed to compare it to other places head to head.  The only thing that matters is that the pie gets larger.  How does that happen?  Entrepreneurs get what they need.

Entrepreneurs are getting what they need in Chicago these days.  There is opportunity.  There is some capital.  There are customers.  There are support networks and connective tissue.  In some startup communities, the holy grail is that a startup founder successfully exits a firm and then starts a venture capital firm.  That’s not happening in Chicago.

Instead, successful startup founders are starting up new firms.

Bryan Johnson, Sean Chou, Andy Bokor, Chris Gladwin, Eric Lekofsky, Brad Keywell and others are actively pursuing new entrepreneurial endeavors.  All of them except for Bryan have chosen to do it in Chicago. There is a Chicago essence in the firms they are building.  They are building firms whose roots go back to the time when the city was built between 1870-1900.

I think we need to stop asking ourselves the questions, “Can it happen here?” or “Can we build it here?”.  I also think we need to shake off our Chicago DNA ingrained insecurities about not being able to measure up.  The answer is it already happened, and it’s built and continues to be built. Chicago measures up.

If you aren’t involved in the startup community, it’s pretty easy to do. Anyone from any age is welcome.  All you have to do is add to the community.  Just come to a meet up.  There are plenty of them that cover every sort of topic you might be interested in.  However, people with their hand out, or only interested in making money off entrepreneurs by providing a pay for service aren’t invited.  Give before you get.

Now, we just need to make it bigger.  The first wave happened and crashed on the beach.  It’s time for the second wave.  It’ll happen.

2 thoughts on “A Short Thought About the Chicago Startup Community

  1. I like your Chicago posts.

    What I’m not getting though is what makes Chicago special–not from an infrastructure but whether this is a fintech world, a media world or simply random.

    In my youth, Chicago to me personally was music and performing arts like comedy. Any of that bubble up into tech investing?

    Be cool to see a list of the successes there.

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