Why Chicago is One of the Best Cities for Entrepreneurs

Why Chicago is One of the Best Cities for Entrepreneurs

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!

More Guides You Will Love

What The Best Presenters Always and Never Do Presentations take on many forms, from slideshows to the more stunning videos that are becoming more commonplace on the internet. As a matter of fact, Computing Forever tells us that of the seven most popular types of videos ...
How Michael Slaby Utilized Technology to Win the ’08 Obama Campaign—and Forever Changed Political Campaigns Whenever I heard about the role technology played in Obama’s campaigns, it read something like this: “Obama seizes victory with social media,” or, “Bush campaign lags in use of digital…leads to GOP failure.” What most of thes...
Should a Non-Technical Founder Learn to Code? "Should I teach myself to code today?" I could spend the next 2 years teaching myself a programming language, and I’d still be a more efficient marketer than coder. I know this, and that’s what continues to hold me back fr...
Skinny Cows Many businesses want to generate a steady return of profits and keep their costs down.  So how can you become a cash cow while maintaining a lean startup business model? A cash cow is a business venture that generates posi...
Startups: What to Do if One of Your Customers Goes Bankrupt Bankruptcy. It’s a pretty scary thought but not an uncommon one to most starters who stare down financial ruin every day. For a minute, forget about your own business or personal bankruptcy and the related specter of ra...
You are Wasting More Time on Social Media Than You Think In a single day, this is the number of times I checked the following applications, whether on my phone, tablet, or laptop: Facebook: 9 LinkedIn: 5 TweetDeck: 17 Instagram: 4 Now, let's say I spent an average of 4...
Six Months Later: Impact Engine and Social Enterprise are Killing It Less than a year ago, I asked a prominent figure in Chicago’s startup community about local investors’ interest in the social enterprise model. She told me flatly, “No one cares.” Well, they care now. Since Impact Engin...
5 Critical Startup Lessons from DoNotRent.com CEO, Mike Cerny Mike Cerny, CEO and founder of the startup DoNotRent.com, a national apartment review and ratings website based in Chicago, knows the challenges of building a company from the ground up. He has faced the typical trials startu...
13 Smart Ways to Spend and Manage Your Startup Money "What's the best financial decision that you've made for your company in the last six months?" This is the question that was posed recently to 13 members of the Young Entrepreneur Council (YEC), an invite-only organization...
The 8 Commandments of Growth Hacking The term “startup” is overused. Too often, we causally connect “startup” with any newly opened organization. I get it, too: startups are exhilarating. Saying you opened a pizza shop or wrote a fledgling business plan just doe...