Why Chicago is One of the Best Cities for Entrepreneurs

by: Adam Lupu

I’m currently on a plane somewhere over Nebraska. I left Chicago an hour ago, and I’m on my way to San Francisco. While I’m out there, I will visit a couple west coast startups, reconnect with old friends, and stop by the old haunts I once frequented. It’s not my first time in the Bay Area. I lived there for six years before returning to my hometown of Chicago. But, I return today with a different perspective on how entrepreneurship works. I’ve seen a new breed of business builders in the midwest. So as I return to San Francisco, I am excited to compare startup culture of the Midwest with that of the Bay. In preparation for this trip, I’m writing down the top five reasons I think Chicago can now be considered one of the premier locations for entrepreneurs to realize their visions.

1.) Revenue over risk

Chicago startups and venture capital firms value strong, tested business models. This is not to say that our counterparts on the coasts do not. It’s merely to say that in Chicago, the number of users you have pales in comparison to the number of paying customers you have. The size of your market is not as important as the revenue it generates. And the value of your professional network is not as critical as the members of your team.

2.) Not changing the game, just playing it better

Chicagoans don’t look for the risky new market; they look for the growth of existing markets and the capitalization of resegmented markets. While Groupon made a big splash with its creation of the daily deals market, there are far more examples of Chicago companies (GrubHub, Belly, Orbitz) taking existing markets and re-imagining them to everyone’s benefit.

3.) Co-working

1871, Catapult, TechNexus, CoLab Evanston, and several other locations offer some of the nicest co-working opportunities for entrepreneurs. More than just opportunities to network, these locations have training and education specifically for startups. Some even have their own residential incubators or business accelerators. If you have a small team and are looking to get started, these co-working locations are a much better choice than a fancy coffee shop or your friend’s garage.

4.) Advice

You don’t need to be part of a startup accelerator to get world-class advice in Chicago. In my experience, it’s the friendliest place for burgeoning entrepreneurs. I have seen lawyers provide multiple hours of free counsel. I’ve attended free talks and workshops featuring accountants, marketeers, data experts, and businessmen. And if you want to get a hold of someone for more personalized advice, they are usually just one or two referrals away. What’s more, they will take your calls and respond to your emails. While the winter weather is always going to be a drawback, there’s nothing cold about the Chicago tech scene. Developers share best practices and work with those just breaking into the craft. Designers hold camps to talk prototyping and strategy. I have never seen a more supportive, accessible community. And when you’re on your own, or a company in its infancy, support and access go a long way to giving you the confidence to keep striving.

5.) Technori, Built In Chicago, Lean Startup Circle, and Excelerate

Not a day goes by in Chicago, when there isn’t a meetup, social event, pitch, workshop, panel, or competition going on. In fact, last Tuesday, there were three going on at the same time, on the same night. Chicago is the only city I know of where you can spend a week attending events with free drinks and food, and come away with all the professional connections you need to drive your business forward for another six months. There are opportunities to meet co-founders, advisors, and talented teammates. And because of the friendly, unassuming, and pretense-free attitude most Chicago entrepreneurs have, you can even form a genuine, lasting friendship.

For these reasons, and several more, Chicago has become a very encouraging space for technologists, entrepreneurs, and makers. When I land in San Francisco, I will be comparing it against a new standard. Chicago’s no-nonsense, cooperative, and vibrant community of business builders make it the location to beat as I consider the future of the craft.

Where does Chicago rank on your list of entrepreneurial hotspots? What advantages do you notice? What challenges do you see the city facing? I welcome your comments below!

About the author Adam Lupu @HowWeLearn
Adam Lupu is a Learning Architect designing and building new structures in education and technology. He is currently founding The Delta Program, a technology training and immersive learning environment specializing in Android Development. Lupu also works with international non-profit Global Playground to unite children across the world in learning and play. A former math and physics teacher, Adam has a Masters in Learning Sciences from Northwestern University and can be found tweeting @HowWeLearn, proudly shouting "Maybe next year!" outside Wrigley Field, or enjoying a Freebirds burrito in Austin, TX.

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