For Rebel One we take pride in elevating entrepreneurs wherever they are. In our ecosystem research report on Chicago we identify the venture capitalists, incubators, accelerators, startups, and other players that help the startup ecosystem flourish. Check out our latest report here.

1. Rebel One Ventures
Startup Ecosystem Analysis:
Chicago, IL
Sergio Marrero, Managing Partner
Vrat Joshi, Analyst

2. City Snapshot
Population | 2.5M (9.7M Metro Area)
Unemployment | 16.4% (2020)
(~3.6% historically | 2019)
GDP | $689.5B (3rd largest, US)
Education System
46 Colleges, 206K+ Students
Top Programs:
Chicago Booth | UC
Chicago Law | UC
University of Illinois
Northwestern University
University of Chicago (UC)
North Dame (feeds into Chicago)
Loyola University
A Bird’s Eye View
RBL1.COM
Sources: Federal Reserve Bank of St. Louis, US Bureau of Labor Statistics
Chicago, IL

3. Venture Capital Ecosystem
Funding Statistics
VC Investment: $2.19B, 278 deals
U.S. Deal Share: ~1.6%
VC Investment per Capita: $226
Top Investment Sectors:
Fintech, Education Tech, Healthtech,
Logistics, AI & Big Data
Macroeconomics of the VC Space
Sources: Pitchbook-NVCA Venture Monitor), Startup Genome
RBL1.COM
Ecosystem Observations
» Diversified venture economy: real estate, insurance, aerospace (value-wise), and
back-office efficiencies
» Residents have deep roots to Chicago; it has built a sticky culture (people want to stay)
» 3rd largest metropolitan U.S. economy: similar venture capital investment total as Miami,
San Diego, and Seattle
» Chicago’s startups create larger impacts locally than they do in the global scale, similar to
ventures in Austin, TX
» Number 1 ecosystem for female founders: 25+% of all startups are female founded
Chicago, IL

4. Funding Options
Looking into the Investors
RBL1.COM
Venture
Capital
Angels &
Angel Groups
Accelerators &
Incubators
Pritzker Group, Hyde Park
Venture Partners, Lightbank,
Jump Capital, ARCH Venture
Partners, OCA Ventures,
Origin Ventures, Chicago
Ventures, Illinois Ventures,
MATH Venture Partners,
Method Capital, Serra
Ventures, Impact Engine,
Cleveland Avenue, Chingona
Ventures
Hyde Park Angels, Angeles
Investors, Ron Levin, Eric
Lefkofsky, Brad Keywell, Mark
Tebbe, Stuart Larkins, Ira
Weiss, Jeff Weiner, Bill Miller,
Brett Hurt, Chris Galvin, David
Galvin, Dean Drako, Tony
Wilkins, Karen Kerr
Healthbox, Techstars Chicago,
Polsky Center for
Entrepreneurship and
Innovation, Elmspring
Accelerator, UofC New
Venture Challenge
Sources: Founder Institute
Chicago, IL

5. Startup Media Channels:
Built In Chicago, ChicagoInno, Chicago Tribune
Blue Sky Innovation, Startup Digest Chicago, 1871
Newsletter, Chicago Tech Events, Tech.CO
Meetups / Community Organizations:
FinTank, Startup Grind Chicago, Chicago Lean Startup
Circle, FUND Conference Chicago
Other Resources
Co-Working Spaces:
1871, Assemble, Blue1647, Catapult Chicago, Colab
Evanston, The Coop, Industrious, MATTER,
TechNexus, WeWork Chicago, Lacuna Artist Lofts
Founder Resources to Gain Knowledge
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Sources: Founder Institute
Chicago, IL

6. Current Leaders & Rising Players
Largest Companies (Market Cap)*:
Allstate, Archer Daniels Midland, Boeing, Caterpillar
Inc, Conagra Brands, Exelon, Kraft Heinz,
McDonald's, Mondelēz International, Sears Holdings,
State Farm, Tyson, United Airlines Holding, US Food
Holdings, Walgreens Boots Alliance
*Major corporate HQ or regional offices
Notable High-Tech Ventures Started:
GrubHub (Food Delivery), Gogo (Airline Service), Orbitz
(Travel Agency), Groupon (E-Commerce), Narrative Science
(Productivity), Coyote Logistics (Logistics), Echo Logistics
(Logistics), Outcome Health (formally ContextMedia –
Healthcare), Belly (Productivity) Raise (Consumer), Uptake
(AI), SpotHero (Logistics), Braintree (FinTech)
Who Dominates the Chicago Economy?
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Sources: Founder Institute
Chicago, IL

7. Economic Activity
RBL1.COM
HealthTech & FinTech Lead the Way
Recent M&A & IPO’s:
» Grubhub, Just Eat Takeaway* | $7.3B
» Give & Go, Mondelēz International | $1.3B
» Tapingo, Grubhub | $150M
» KLX, Boeing | $3.2B
» Braintree, Paypal | $800M
» Venmo, Braintree | $26.2M
» Agrible, Nutrien | $63M
» Level Ex, Brainlab | Undisclosed
» GoHealth IPO (GOCO) | $6.6B (MC)
» Grubhub IPO (GRUB) | $2.03B (MC)
» Sprout Social IPO (SPT) | $814M (MC)
Top Ranked Startups:
» Lightstream | Media & Design Software
» FanFood | Food Products
» Livly | Real Estate Services
» Healthjoy | Healthcare Tech
» Upshow | Media & Information
» Capital Markets Gateway | Fintech
» SpotHero | Automotive
» Cresco Labs | Cannabis
» Cameo | Entertainment / Social Media
» Elevate K-12 | EdTech
» Fooda | Food Products
» CashDrop | Fintech & Food
(Acquired, Acquiree | Deal Value), Market Cap at IPO, *deal has yet to complete, (current date: Q1 2021)
Sources: Pitchbook, Crunchbase, Chicago Business Journal M&A
Chicago, IL

8. Map / Region Insights:
» Major startup spaces and players are highly
concentrated in the “River North” and Loop area,
specifically in Merchandise Mart building (houses
1871 and MATTR). Other budding communities
include Wicker Park, West Loop, and Pilsen.
» While educational institutions are
entrepreneurially focused, they mostly exist in
different parts of the city (e.g. Northwestern
University in Evanston, IL)
» Most Chicago startups are being acquired by
larger corporate firms in the city
» About ⅓ of startups are founded / run by women
» 45% of Chicago's investments have a 10X ROI
compared to 25% for the Bay. Also, highest MOIC
of all cities 5.5X from 2006 – 2018.
» Raised $351 million Q1 2020, down -3.8% YoY
Area Insights
Venture Capital Accelerator / Incubator Co-Working
Sources: Startup Genome
RBL1.COM
Analyzing the Geographic and Economic Reach Chicago, IL

9. Analysis
Feedback from locals immersed in the ecosystem:
» Many Midwest investors are considered “old money” that perpetuate
a culture of more conservative investment risk tolerance
» Local community has a lack of institutional support for experimentation
(e.g. free cohorting spaces such as AWS Loft)
» Local entrepreneurs while interested in entrepreneurship are less
focused on high growth tech ventures
» More capital exists than skilled talent with the experience and
management training
» Limited funding opportunities leading Seed and Series A investments
and beyond between the pre-seed and growth phase
Subject Matter Expert: Julie Martin, Dan Eidell, Samara Hernandez, 1871
RBL1.COM
Insight from Local Subject Matter Experts Chicago, IL

10. The startup ecosystem in Chicago has been a source of innovation across
industries with an increasingly strong presence in the Food and AdTech space
among many others. Reviewing the profile of the metropolitan area, while the
economy is diverse and large (3rd largest metropolitan market in the U.S.), it is
ranked lower than other entrepreneurial ecosystems in terms of total startups
and venture capital dollars deployed annually. The reason for this is a tight local
connection, but a weaker link to the global scale. Many exits are with large
corporations within the city, rather than well-broadcasted IPO’s or other
acquisitions outside of Chicago: this indicates a strong link within the local
community. For Chicago to continue expanding, it is imperative the city looks to
scale. In other news, there is movement linked with major tech companies such
as Google, Salesforce, Amazon, and Facebook which have been establishing
operations in the city over the past 5-10 years. We believe this will result in more
trained executives with capital leaving those institutions to start companies in the
coming years.
State of the Market
Sources:
Interviews: Julie Martin, Dan Eidell, Samara Hernandez, 1871
https://fi.co/insight/the-chicago-startup-ecosystem-canvas-a-giant-list-of-startup-resources-in-chicago, http://www.worldbusinesschicago.com/data/chicago-business-overview
https://www.bizjournals.com/chicago/news/banking-and-financial-services/mergers-and-acquisitions,
https://www.bloomberg.com/news/articles/2018-03-27/the-extreme-geographic-inequality-of-high-tech-venture-capital, https://files.pitchbook.com/website/files/pdf/2018_Chicago_Venture_Ecosystem_AHH.pdf
https://www.americaninno.com/chicago/inno-insights-chicago/chicago-sees-strong-year-in-vc-funding-with-2-2b-raised-in-2019/#:~:text=Chicago%20companies%20raised%20%242.186%20billion,and%20%241.3%20
billion%20in%202016, https://www.flaticon.com/, https://www.bls.gov/eag/eag.il_chicago_md.htm, https://fred.stlouisfed.org/series/NGMP16980,
https://www.bizjournals.com/chicago/news/2020/05/31/chicago-startups-raise-68m-in-may.html#:~:text=Chicago%20startups%20raised%20%24351%20million,economy%20due%20to%20Covid%2D19.
https://startupgenome.com/reports/global-startup-ecosystem-report-2019, https://startupgenome.com/reports/gser2020
Analysis
Chicago, IL