Top 10 wonderful Windy City tech startups
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Chicago, the Midwest balance point of New York and Los Angeles, beats everyone in toughness and tech startups

Chicago, the City of Big Shoulders, the Windy City, the city of immigrants – and the third largest city in the U.S. with over 2.7 million busy people scurrying around the shores of Lake Michigan. Are you a Batman fan? You should know that Gotham City is Chicago, not New York, so rethink your superhero locales.

Everything that makes a big city a big city is in Chicago. All major sports teams, including the Chicago Cubs baseball team that lifted their curse, finally, with a World Series win in 2016. Huge skyscrapers. Multiple major universities such as the University of Chicago, Northwestern, Loyola, and DePaul.

Research schools combined with a financial center and city and state government offices make for an active startup culture. The unofficial “Capital of the Mid-West” beckons those striving for better in the middle of the country and the middle of the action.


Photo courtesy: Groupon

Everybody loves a deal, and Groupon started the “deal of the day” marketing phenomena and still casts the biggest shadow. Seems like every business and service has used Groupons for marketing to new customers from the corner bakery to the global behemoths.

First angel money arrived in early 2007 ($1 million), but the official company start date is November 2008, helped along by another $4.8 million in January of that year. The pile keeps getting bigger, with $30 million Series B, $135 million Series C, and a whopping $950 million Series D money in January 2011. IPO money, $250 million, brings the total investment to a staggering $1.39 Billion.

IRI Worldwide

Photo courtesy: IRI Worldwide

1979 was when IRI Worldwide opened their doors offering analytical support. Dull? Maybe, and they rocked along their merry marketing way when suddenly Big Data got Big for real and IRI turned research into consumer and media number crunching into predictive analytics. They now reach from retail to finance to healthcare and more.

While 1979 may be too old for a startup, 2011 certainly isn’t. That’s when IRI received $85 million in venture funding from New Mountain Capital. The same group plopped down another $96+ million in July of 2016 for a pile $181 million high.


Photo courtesy: GrubHub

The first company in the food pickup-and-delivery business to gain mindshare space in the brains of the public, GrubHub started in 2004 trying to leverage the Internet for food pickup requests. Remember, the iPhone didn’t appear until 2007, so co-founders Matt Maloney and Mike Evans got in way early. Worked, too, since now they cooperate with more than 20,000 restaurants in more than 500 cities.

Cooking on low for several years, GrubHub didn’t grab any Series A money until November, 2007, and that was only $1.1 million. That went well, and a Series B round, also from Origin Ventures, added another $2 million in March 2009. November 2010 saw $11 million in Series C money, followed by $20 million Series D bucks in March 2011, and another $50 million in Series E in September 2011. Last funds came from an undisclosed amount from Private Equity. Total investment is around $84 million.

Sprout Social

Photo courtesy: Sprout Social

Companies that want to benefit from social media today need to manage that social media interaction. One way to do that is work with Sprout Social, a company that believes “the world is better when businesses and customers communicate freely.” They also help hook enthusiasts, a small percentage of whom can drive a large groundswell of good will and business.

Somewhat late to the social media world, Sprout Social opened up in 2010, buoyed by an undisclosed Series A placement in May of that year. November came with $1 million in seed money, followed by $10 million and $8 million of Series B fundings in June 2014. An indication of success is the $42 million Series C money that came in February 2016, bringing the total investment to $61 million.

G2 Crowd

Photo courtesy: G2 Crowd

Who do you trust for software reviews? Your neighbor? A website you never heard of? How about your peers, thousands of them, all gathered together on the G2 Crowd website? Over 100,000 software users from companies small to huge give and get honest feedback that G2 Crowd turns into crowd-sourced data.

First reviews began in the spring of 2012, and $2 million in seed bucks arrived in February 2013. Angel money appeared in May 2014 ($2.5 million) and $7 million in Series A came in July 2015. Big splash? $30 million in May 2017, stacking the total up to nearly $46 million.


Photo courtesy: Yello

Chicago companies employ hundreds of thousands already, and when they need more they can call Yello to help solve their “talent acquisition” problems. Yes, it’s a digitally wonderful age, but HR still often collects paper resumes at career fairs. Yello helps companies identify, track, lure, and interview candidates with hooks like a mobile app and video interviews. Sure beats a Rolodex (ask your grandfather).

Opening the doors in the heat of 2008’s summer, Yello sweated out their development until Series A funding of $6 million appeared in the fall of 2014. A year later, Series B money ($5 million) arrived, followed by $4.2 million in Series B money in August 2016. Finally, $31 million in Series C funds from JMI Equity came in June 2017 putting their total investment just north of $42 million.

Narrative Science

Photo courtesy: Narrative Science

Data is everywhere and can be overwhelming and cold, but not when companies like Narrative Science “humanize” the data to make it work for businesses. A world leader in “Advanced Natural Language Generation” with its Quill program, Narrative Science’s customer list is heavy with heavyweights like Credit Suisse, MasterCard, intelligence agencies, and USAA (also an early investor).

Founded in 2010, which is fairly early in the big data market, Narrative opened their doors with venture money to the tune of $1.35 million. January 2011 came with $6 million in Series B funding, then $3 million in debt financing in July 2012. Big piles include Series C of $11.5 million in September 2013, $10 million of Series D in November 2014, and $11 million Series D again in April 2017 for a total of $43.4 million.


Photo courtesy: Snapsheet

What do people love more than their phones? Cars! And using their phones in their cars, leading to a sudden need for repairs. Luckily, Snapsheet does exactly that. The free app lets owners of crumpled fenders photo, describe, and broadcast their repair needs to local autobody shops.

Snapsheet started uncrumpling their first fender in 2010, and collected $250k in seed bucks in September 2011. Four months later, Series A money totaling $1 million drove in, followed by three undisclosed venture rounds. Listed rounds include $10 million in December 2013, $20 million in October 2016, and just recently $12 million in Series D in June 2017. That’s a bumper crop of $43.25 million.


Photo courtesy: ShipBob

One way Amazon wins so often? Great shipping logistics. But they have warehouses full of money, so how do small companies compete? Call ShipBob. They promise to leverage their smarts and shipping contacts to give a small biz the same transport logistics as the really big guys.

2014 seems late for shipping support, especially since Benjamin Franklin was appointed the first postmaster general in 1775. But ShipBob started fast, turning an initial $20k in seed bucks into $1 million seed money in April 2015, then $4 million 13 months later. Biggest box of bucks? $17.5 million from Bain Capital in June 2017, meaning a total of $22.52 million.

CloudCraze LLC

Photo courtesy: CloudCraze

Salesforce usually gets labeled as the primary Software As A Service “shining example” with good reason. CloudCraze has built their business by filling in the gaps for customers. Hooking the Salesforce information to ecommerce, sales, marketing, and service, CloudCraze has signed up some of the biggest companies in the world (Coca-Cola anyone?).

Doors opened in 2009, not terribly long after Salesforce appeared. August 2015 saw $10.63 million in venture funding appear. That was followed in January 2017 by Insight Venture Partners Series A placement of $20 million.

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James Gaskin

About James Gaskin

James writes books, articles, and jokes about technology, and consults for those who don’t read his books and articles.

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