Chicago, it goes by many names: The Windy City, Chi-Town, and Chicagoland. I’ve even heard some people on the West Coast Best Coast call it the Los Angeles of the Midwest. Alternatively there are those on the East Coast that call it the New York of the Midwest.
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However, regardless of where you hail from, I think we should move past the small potatoes here and give Chicago some much deserved love. Sure, they have amazing museums, great pizza, and winning sports teams, but that’s not why they deserve our recognition today.
Rather, Chicago has one of the strongest crops of entrepreneurs who put the entirety of their being into building companies which elevate the people, the city, the region, and ultimately America. To that end, I went out and talked with some of the embedded, local entrepreneurs who know the ins and outs of Chicago better than most.
I asked them all one question: what makes Chicago’s landscape so awesome? I think you’ll find their answers inspiring and interesting.
Here are 9 entrepreneurs who love their city, and they’re not afraid to show it:
Abby Ross – COO – ThinkCERCA
“There are three main points: collaboration, physical spaces, and a supportive community. I work hand in hand with my CEO Eileen Murphy Buckley, who has decades of education and administration experience. But this isn’t the only opportunity I have to collaborate with people outside of traditional entrepreneurial spaces though – Chicago’s open and inclusive startup ecosystem affords an opportunity to collaborate with people from a number of different backgrounds.
And when it comes to places to work, Chicago houses coworking spaces across the city that give entrepreneurs the space they need to jumpstart their company without the headache of finding a place and furnishing it alongside running the actual business. Great example: ThinkCERCA started off at 1871, a collaborative space where entrepreneurs can focus on the work and less on the office administration.
There are also startup accelerators like Impact Engine, which gave me the confidence to create a company that would have a meaningful impact. Because of this support, I was able to scale ThinkCERCA to reach more students, and help schools achieve the only thing in this business that matters the most: student outcomes.”
Robert Haidari – Founder – Hot Emu
“Chicago is a big city with a small town feel: I love it. Business is done the traditional way, based on trust and respect. If a business wants to operate it has to try its best to satisfy clients, employees, partners, and investors. And everyone knows each other, whether they’re inquiring about someone’s work history, getting in touch with a potential business partner, or finding a mentor – everyone is within reach.
We also have a lot of great talent. Chicago universities are top ranked and produce a lot of graduates, which gives the startups here a wide range of potential employees. Not to mention we’re surrounded by various industries, many of them ripe for disruption.
In the middle of a highly concentrated pool of businesses, with money to spend and appetite to get ahead, I’m often asked if I would ever relocate to either coast. Never. Chicago has a very special feel to it, and I owe this city everything I have accomplished.”
Hazem Dawani – Cofounder – OptionsCity
“As a trading technology company, there is no better city in the world than Chicago. Obviously this is a market center, and the home of the world’s largest futures exchange, huge hedge funds, major trading firms, and other global companies that are active in the markets.
But the key is that when you combine that environment with a deep, talented, and stable labor pool, particularly of tech talent, it becomes an even better place for a business like ours. Every day I’m reminded of just how lucky we are to be in Chicago.”
Craig Vodnik – Cofounder – Cleverbridge
“Our first office was a 300 square foot space that cost about $600 a month. Today, the 1871 offers something even more attractive than what we had, but to start out, that was a very reasonable cost. Once we started hiring, we were finding really motivated and sharp people that wanted to work for an ecommerce company, not only for the job, but also for the career path that we would set them on. In California, companies are competing with Facebook, Twitter, and Google for the best talent and that free market thinking results in more outrageous costs all the time.
Obviously, being a Chicagoan, I had a support structure that I could call on in a pinch to help out, whether that was one friend answering phones for a week while I was in Germany or another friend shipping boxes from my house while I was at a tradeshow for three days.
Also, while there’s a 7 hour time difference to Germany, there’s a big difference in having two hours of workday overlap each day versus having none, which is what would have happened had we been based in California.
Not to mention I’ve seen what goes on in California, and Midwestern attitudes towards hard work, loyalty, and trust are intangibly important for an entrepreneur to build a successful business. Does your key salesperson come to you and talk about the recruiters hunting him down, or does he stay silent, always listening for the best offer and then jump ship after a year?”
Joseph Collins – Cofounder – Markr
“It’s all about the community. The 1871 is a great example of this: when the City of Chicago passed a law on SaaS companies that was going to hurt a lot of Chicago startups, 1871 was able to get in the ear of the mayor. Further, they were instrumental in influencing the Mayor to change the law and help the startups. I don’t know if there are many other cities that do that, or places that will help small startups in that way.”
Stephen George – Cofounder and COO – IndiCard
“Chicago’s diverse service economy gives IndiCard the perfect market to truly build a brand that we can then roll out to any city in the country. I’ve found that when Chicagoans get it, they get it and they love it. Businesses and individuals are inundated with so much technology here in Chicago that we really have to differentiate ourselves from the rest of the pack. Since we have a proven brand and product here in Chicago, we have a great foundation for success in our other live market like Denver and Las Vegas.”
Darren Guccione – CEO – Keeper Security
“I was born in Chicago, have lived here most of my life, studied Engineering at the University of Illinois, and have built my companies here. My family and I love living here – except when it’s 30 degrees below zero :).
The tech startup ecosystem has grown into something I would describe as amazing. There are so many creative entrepreneurs here that are challenging the ways we interact with technology, innovating, and creating environments to help each other succeed with organizations like 1871, Matter, TechStars, and Catapult.
Despite being a big city, we know how to stay both humble and grounded – this city is all about a no-BS attitude and disposition focused on execution. People are cool, friendly, and in the sincere Midwestern way, welcoming to newcomers. My team in Chicago is an extension of this, and they are some of the most dedicated, smart, and creative people I’ve ever worked with.”
Adam Fridman – Founder – Mabbly and Meet Advisors
“Chicago’s entrepreneurship community is exploding and the growth is daily and visible. It’s driven partly by the energy of the city itself but also by a wave of young people who are highly motivated to create their own spaces, both personally and outside the shadows of New York and San Francisco.
The good news is that Chicago’s startup community and culture are evolving so quickly that there are overwhelming events and opportunities like 1871, Technori, and SBAC. Finding the right one can be a challenge, so trying many different things and keeping an open ear are keys to getting the most of what’s happening in Chicago now.”
Greg Fenton – CEO and Tim Haitaian – CFO or RedShelf
“We think the Chicago tech ecosystem is the perfect place to be. Because we have team that is majority made up of individuals under the age of 30 that live downtown, it provides the best atmosphere to get to and from work. We love that our office is surrounded by art galleries, pubs, and bars to enjoy a few cold ones after working hard all day.
Greg considers working in Chicago and being a part of the tech startup ecosystem like summer camp for adults. There are so many different pieces of Chicago that one or a group of people can experience and do together, whether it’s after work on a Thursday night or getting together as team on a Saturday to go sailing.
Having a team full of different personalities, we chose Chicago as our headquarters because it has something to offer everyone’s personal tastes and preferences. And our office is pretty sweet, too!”