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CHICAGO
Before the region was known as “Silicon Prairie,” VCs called Chicago “the flyover city” as they jetted from Silicon Valley to Boston looking for startups to invest in. As no industry dominates the city, startups in Chicago are diverse. And with colleges like Northwestern, Urbana-Champaign (UIUC), and University of Chicago so close by, the talent is all around. Treated like an ex by the founders of Netscape, PayPal, YouTube, and Yelp—who all ventured to the Valley to begin their companies—Chicago finally found a friend in Groupon, where the fingerprints of cofounders Eric Lefkofsky and Brad Keywell are still left all over the Chicago tech scene. With its affordable prices and insistence on no ketchup on hotdogs, the Chicago startup scene hopes to embody the values of its largest incubator, 1871, named after not the Great Chicago Fire, but the innovation and teamwork that came after it.
VENTURE ACTIVITY Q4’15 - Q3’16
VC FUNDING: $1.8B
DEALS: 275
EXITS 100
5 YEAR YoY FUNDING GROWTH: 14.6%
5 YEAR YoY DEAL GROWTH: 10.8%
Source: CB Insights
CHICAGO AT A GLANCE
Power Breakfast
Chicago Cut
Lou Mitchell’s
Pierrot Gourmet
The Bagel
Yolk
Coffee Shops to Start Up In
Goddess & the Baker
Intelligentsia
La Colombe
Sip Coffee House
Best Bars
Big Star
Lotties
Lux
Parlor
RL
The Aviary
Local Beer
312
Forbidden Root
Goose Island
Old Style
Go-to Shot
Fireball
Malört
Offline Tinders
Delilahs
Fado
Original Mother’s
Richards Bar
Soho H.
The Hangge Uppe
Underground
“Must Be At” Local Events
Air and Water Show
Art Expo
Blackhawks/Cubs/Bulls Game
Chicago Gournet
Lollapalooza
Old Town Art Fair
Navy Pier Fireworks
Second City
Taste of Chicago
TJ & Dave at iO
THE TOP
ANGELS
David Cohen
Deborah Quazzo
Harper Reed
Howard Tullman
Kevin Willer
Jason Fried
VCs
Apex Venture Partners
GSV Acceleration
GSV Ventures
Hyde Park Angels
LightBank
Pritzker Group
True North
Valor Equity
TOP ACCELERATORS
1871
BLUE1647
Catapult
HealthBox
Impact Engine
Matter
TechNexus
Techstars
U of Chicago New Venture Challenge
University Technology Park at IIT
ENTREPRENEURSHIP EVENTS
1871 TGIFs
Blogcademy
BMA
Chicago Startup Weekend
Chicago Venture Summit
Techweek Chicago
Q4’15 - Q3’16 TOP FUNDING ROUNDS
Avant—$325M
DuPage Medical Group—$250M
The Onion—$200M
SMS Assist—$150M
Vibes Media—$45M
Uptake—$45M
THE PAYPAL MAFIA
Chicago was once home to one of the most powerful mob groups of all time—the PayPal Mafia, many of whom once called UIUC their home. These individuals have had big roles in quite a few legendary companies.
TEAM MEMBER: Elon Musk
PAYPAL POSITION: Cofounder, Director
AFTER PAYPAL: Founder and CEO, SpaceX
Cofounder and CEO, Tesla
TEAM MEMBER: Peter Thiel
PAYPAL POSITION: Cofounder, CEO
AFTER PAYPAL: Managing Partner, Founders Fund
President, Clarium Capital
Board Director, Facebook
TEAM MEMBER: Max Levchin
PAYPAL POSITION: Cofounder, CTO 
AFTER PAYPAL: Chairman, Yelp; CEO, Affirm
Executive Chairman, Glow
Founder, Slide (acquired by Google)
TEAM MEMBER: Reid Hoffman
PAYPAL POSITION: Executive VP
AFTER PAYPAL: Cofounder and Executive Chairman, LinkedIn
Partner, Greylock
TEAM MEMBER: Keith Rabois
PAYPAL POSITION: Executive VP, Business Development
AFTER PAYPAL: Partner, Khosla Ventures
COO, Square
Investor, YouTube, Geni, LinkedIn, Yelp
TEAM MEMBER: Roelof Botha
PAYPAL POSITION: CFO
AFTER PAYPAL: Managing Partner, Sequoia Capital
TEAM MEMBER: Jeremy Stoppelman
PAYPAL POSITION: VP Engineering
AFTER PAYPAL: Cofounder and CEO, Yelp
TEAM MEMBER: Russel Simmons
PAYPAL POSITION: Engineer
AFTER PAYPAL: Cofounder, Yelp
TEAM MEMBER: Steve Chen
PAYPAL POSITION: Engineer
AFTER PAYPAL: Cofounder, YouTube
TEAM MEMBER: Jawed Karim
PAYPAL POSITION: Engineer
AFTER PAYPAL: Cofounder, YouTube
TEAM MEMBER: Chad Hurley
PAYPAL POSITION: Designer
AFTER PAYPAL: Cofounder, YouTube
TEAM MEMBER: David Sacks
PAYPAL POSITION: COO
AFTER PAYPAL: CEO, Zenefits
Cofounder and CEO, Yammer
Chairman, Geni
TEAM MEMBER: Dave McClure
PAYPAL POSITION: Director Marketing
AFTER PAYPAL: Advisor, Kiva
Founding Partner, 500 Startups
TEAM MEMBER: Premal Shah
PAYPAL POSITION: Product Manager
AFTER PAYPAL: President, Kiva
Note: UIUC grads are marked with UIUC logo.
Navigating One of the Best Music Festivals in The US
1 Cell Phones. Cell phones present a confounding conundrum for the average Lollapaloozer. On the one hand, they can be used to take pictures and videos for your 160-second snap story documenting the day’s antics, but on the other, will have unreliable service and power in the area. As bulky as they are, walkie talkies or messenger hawks could be used as alternatives.
2 Transportation. On the one hand, there’s the option of driving and parking. This method is sobriety inducing and cost ineffective. The second is public transportation—it can make for a good ride with a couple hundred other drunken festival-goers, but if one person throws up, it’s game over. We like cycling—plenty of places to park and the winds of the Windy City helping erase the ringing in your ears after Metallica.
3 Music. Choose one stage and stick with it—movement means leaving your friend who is looking for the port-a-potty behind, as well as functionally watching a live performance thousands of feet away on a TV.
WHEN: Last Weekend of July
WHERE: Grant Park, Chicago
ENTREPRENEURSHIP IN ACTION
Led by Founding President Josephine Lee, Northwestern was able to create its own entrepreneurship club, EPIC (Entrepreneurs Pioneers Innovators Creators). We interviewed the past president of EPIC, Suzee Han.
What does EPIC do? Before EPIC, there was a more fragmented entrepreneurship scene on campus. The past president rebranded and re-created the club with the help of advisors like [GSV Vice President] Li Jiang. I helped Jo create an entrepreneurship development program that spanned nine weeks. It was student run and we brought in professors and CEOs to teach various aspects of how to build a startup. We also launched our first hackathon, had a startup career fair, and had a large business competition that grew to such an enormous size that we couldn’t even imagine.
Who was the biggest speaker you brought in? With the help of the Farley Center, we brought in Peter Thiel. It was extremely exciting for us because he’s one of the top investors in Silicon Valley, was an early investor in Facebook (not to mention a founder of PayPal and Don of the PayPal Mafia). It was a great event. The event was coincidentally the first Monday of finals week, so people finished their finals early just to attend!
What was the club’s vision? Northwestern is a very pre-professional campus. There are a lot of students who strive to be consultants, professors, or bankers—entrepreneurship is growing but it’s not quite there yet. As such, we just wanted to create a more entrepreneurial campus because the entrepreneurial mind-set is important no matter what path you take. Our mission was to build an entrepreneurial community for everyone at Northwestern.