Chicago, across many dimensions, is a city that鈥檚 second to none. With apologies to Milwaukee, Detroit, Toronto, and those averse to puns about the Great Lakes, Chicago鈥檚 urban lakefront is truly superior, as is the restaurant scene. A crown on the nation鈥檚 breadbasket, it鈥檚 through the city鈥檚 exchanges that the world trades its agricultural commodities and financial derivative products, like options and swaps.
Subscribe to the Crunchbase Daily
But for a city whose latest fortune was born on the back of futures contracts, its startup founders lag behind others in capital to build the future. However, like the level of Lake Michigan itself, this too is on the rise.
According to Crunchbase data, startups in the greater Chicago metro area (which also includes places like Evanston and Naperville) have raised nearly $850 million in reported funding across nearly 90 VC rounds, year to date. Keep in mind that this is based on analysis of private-market data, which especially at seed and early stages is subject to reporting delays. Actual deal and dollar volumes are likely higher than what鈥檚 reported here, but this is enough to indicate, directionally, where Chicago鈥檚 startup ecosystem is at right now.
Dollar volume is, generally, on the rise. And that鈥檚 because Chicago deals are growing larger. For example: in 2018, the average early stage round (Series A or Series B, with some subsets of other round types too) topped out at roughly $6.5 million across 104 rounds. So far in 2019, the 36 reported early-stage rounds average out to $10.9 million. This doesn鈥檛 include the Cameo round, for which dollar amounts haven鈥檛 been publicly disclosed. The biggest early-stage deals so far include additive manufacturing firm , car insurance marketplace company , and a for , which uses specialized organisms and fermentation processes to produce nutritious proteins.
Similarly, at late stage (Series C and later), average deal size is up from $40 million in 2018 to $63 million in 2019 year-to-date, though cancer analytics company from May is primarily responsible for driving up this year鈥檚 late-stage mean.
Though reporting delays and the stealthy nature of seed-stage startups makes it difficult to quantify activity closest to the entrepreneurial metal, it certainly feels as though things are picking up at this end of the venture life cycle as well. In the past quarter, several Chicago-based startups picked up seed funding; these include: practice management software provider , code-less app builder , travel inspiration and planning platform , at-home dialysis startup , new nail salon experience , restaurant repair service , and mobile healthcare company , which have raised seed funding since April 1.
All’s not so rosy in Chicagoland tech though.
One of Chicago’s highest-flying unicorns came crashing back to earth in early May. , which makes money by displaying pharmaceutical advertisements in physician waiting rooms, led by middle-market PE firm . According , the transaction involved less than $100 million. The valuation of Outcome Health following the re-cap wasn’t disclosed, though Crain’s also reports that in Outcome Health, indicating its share value declined precipitously from its last financing.
Outcome Health raised in late May 2017. led the deal, in which , Google growth investment arm , and (a firm founded by current Illinois governor JB Pritzker) also participated, according to Crunchbase data. However, in November 2017 reveals other investors, including and Laurene Powell Jobs’s , among the ad firm’s backers.
At issue in that lawsuit? Fraud, and the fate of $225 million held in a subsidiary of Outcome Health called Gravitas Holdings. The cash was ostensibly earmarked for direct payout to Outcome鈥檚 founders, and , who led the company while it allegedly it was delivering in patient waiting rooms. Reports of said misrepresentation prompted by the U.S. Department of Justice and, ultimately, the lawsuit seeking to prevent the capital transfer. In January 2018, Shah and Agarwal and agreed to use $159 million of the $225 million held by Gravitas Holdings to reinvest in the business and pay down its debts, according to the Chicago Tribune. The settlement allowed Outcome to disburse remaining capital out of Gravitas Holdings, presumably back to Shah and Agarwal, who left their leadership roles at the company at that time. As part of the recapitalization event announced in May, Shah and Agarwal are out as stakeholders in the company, according to .
The reputation of Chicago鈥檚 startup ecosystem will take time and a long string of successes to make up for such a high-profile flameout and fraud scandal.
Despite being the third largest city by population, Chicago ranks ninth in known venture dollar volume (behind San Diego, Seattle, and Austin) and sixth (behind Boston, Los Angeles, and Seattle) in venture deal volume, year to date. San Francisco and NYC, respectively, retain the top two spots for both metrics.
There鈥檚 a lot of progress to be made, and Chicagoans are known for building. Here鈥檚 to hoping the third decade of the 21st century shapes up better for Chicago鈥檚 startup scene, and with fewer bad apples to boot.
Stay up to date with recent funding rounds, acquisitions, and more with the Crunchbase Daily.



67.1K Followers