Harper Reed

5 Damn Good Reasons to Startup in Chicago

If you’re not from Chicago, the extent of your Chicago knowledge might boil down to deep-dish pizza and “My Kind of Town.” But look a little closer, and you’ll find a thriving technology scene – and some damn good reasons to startup in Chicago. This celebration of the Chicago ecosystem is brought to you by @properties, the leading Chicago real estate brokerage serving both the city of Chicago and North Shore through dynamic marketing and innovation. Read more here!
If you’re a local thinking about an entrepreneurial career, or a non-Chicagoan looking for a place to set up shop, here are some reasons to consider the Windy City.
1. Local success stories
It might not have spawned the likes of Google or Apple, but Chicago has been the birthplace of some great startups – and some great entrepreneurs. Founded in 2004, GrubHub went on to raise over $80 million, acquire four companies – including Seamless – and go public in April of last year. Love it or hate it, Chicago-born Groupon has managed to raise over $1 billion and acquire 33 companies since opening its doors in 2008 – and went public in just three years.
On the other side of the spectrum, Jason Fried’s Basecamp – founded in 1999 as 37signals – has remained staunchly independent. The only investment they’ve taken was from Amazon founder Jeff Bezos in 2006, and their goal is to stay in business for the long haul.
You’ll also find Harper Reed in Chicago, who went from CTO of Threadless to CTO of Obama for America. Now, he’s started his own company called Modest, which offers a mobile commerce platform. From food to productivity to politics, Chicago boasts many success stories to inspire you.

2. The Midwest mentality
Entrepreneurs in Chicago are proud to build solid companies that earn revenue. You’re less likely to come across cool little free apps with no monetization strategy in sight. For the budding entrepreneur, this means you’ll be encouraged to figure out how to survive, grow, and stay in business.

“I think Chicago could be a great place for building bootstrapped companies, long-term companies, companies that are focused on selling stuff, on revenues and profits,” Fried told us. “I think that represents the City of Big Shoulders, that represents the hard-working Midwest, the whole ethos here.”

Other startup scenes focus on “blowing things up fast” and not on making money, Fried said, and that’s a “dangerous, dangerous thing.”
3. Strong community
In July 2006, we held our first-ever Tech Cocktail event in Chicago. Startups were becoming popular, and we wanted to give entrepreneurs a way to connect and show off their creations. Almost 250 attendees showed up to mingle and check out the six showcased startups, including investors, developers, designers, and hackers.
Almost 10 years later, the startup community in Chicago is thriving. You can find support at innovation hubs like 1871, Sandbox Industries, and TechNexus, or get accelerated by Techstars Chicago, Impact Engine, or Healthbox Chicago. If you don’t have an office and don’t want to work from home, you can sign up for coworking at Catapult, CoLab, Grind, Industrious, Platform Coworking, WeWork, or one of the many other spaces around the city.
According to AngelList, there are over 2,000 startups and about 750 angel investors in Chicago. Many of them come out to the multiple startup events that happen every night (see Built in Chicago’s events board). Startup Institute Chicago also hosts events to help newcomers find out about the Chicago startup scene and find a job at a startup. Many of the local colleges – including Loyola Chicago, DePaul, Northwestern, and the University of Chicago – have entrepreneurship programs to expose young people to the field.
And every year, more than 10,000 people from around the country gather for the Techweek conference. There’s no shortage of support organizations, places, or events to help you in your startup journey.
4. Support for women
According to one survey, Chicago has 24% women in its startup scene – below the national average of 29% – and the locals are trying to change that.
Ms. Tech is a collaborative forum of hundreds of women that was founded in 2010 as a simple Facebook group. Now, Ms. Tech holds networking and educational events to help women grow their business, network, and find valuable resources. Other local organizations supporting women entrepreneurs include SimplyBe TV and The Founding Moms.
Many national organizations have local chapters based in Chicago, such as Women in Technology International, Lesbians Who Tech, Women Who Code, Girl Develop It, and Women 2.0.
Chicago women are also willing to speak up for a more inclusive community. When Techweek published what some thought was a sexist ad for a rave party, the community started a dialogue – including this open letter by Built in Chicago CEO Maria Christopoulos Katris. Community leaders will be the first to say there is room for improvement, but at least the issue is on the table.
5. Food and fun
Every summer, Chicagoans come out for the huge Taste of Chicago outdoor food festival. Think deep dish pizza, hot dogs, and so much more – a symbol of the city’s culinary pride.
Deep dish pizza from Giordano’s
When you’re not working, Chicago has tons of outdoor activities to help you recharge and relax. Walk through Lincoln Park or Millennium Park, home of The Bean (a huge mirrored public sculpture in the shape of, yes, a bean). Spend a day at the beach or the zoo. Watch the city come alive with street festivals, parades, and farmers markets. Or just explore Chicago’s diverse neighborhoods, from Pilsen to Little Village to Humboldt Park to Greektown and Little Italy. It’s no wonder almost 3 million people choose to make Chicago their home.

Harper Reed image credit: Joi Ito / Flickr / CC BY-SA 2.0
Pizza image credit: Eric Chan / Wikimedia Foundation / CC BY-SA 2.0
Bean image credit: Robert Lowe / Flickr / CC BY-SA 2.0