About - Chicago Ventures

Chicago Ventures launched in 2012 with support from Chicago’s leading entrepreneurs and investors.

They noticed that Chicago and the central region of the country had many of the ingredients of successful startup communities: dedication to building sustainable businesses, strong quality of life and low cost of living, close proximity to over a third of all Fortune 500 companies, and top-notch university systems — missing, though, was access to smart, connected, experienced capital.

That’s why we’re here.

We understand that entrepreneurs need varying levels of guidance from their investors. While we can’t speak for ourselves, the companies we invest in tell us that our ability to resonate with them as entrepreneurs — and connect with them as people — is an added bonus to our operator backgrounds and network of investors and advisors, customers, talent, and later-stage investors.

[Don’t take our word for it. Ask them directly.]

Investment focus

We invest in tech-enabled businesses with each initial investment, generally into a seed round, ranging from $750K – $1M.

We invest in both enterprise and consumer businesses — with investments in analytics, B2B2C, sales and marketing SaaS, payments/loyalty, healthcare IT, and marketplace/on-demand services.

We’re committed to supporting our companies during their early growth. In fact, we have the highest “smart money” follow-on rate for all micro VCs outside of the coasts.

Our team

Our team is a group of operators with deep roots in the Chicago tech community.

Investment Committee

Godard Abel SVP and GM (previously CEO) SteelBrick; Co-Founder/Chairman, G2 Crowd // Chicago Ventures EP
Godard Abel

Godard Abel

SVP and GM (previously CEO) SteelBrick; Co-Founder/Chairman, G2 Crowd // Chicago Ventures EP

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Godard previously founded SteelBrick (acquired by Salesforce in 2015 for $360 million), and BigMachines, a leading software as a service (SaaS) provider which he grew profitably from scratch to $50 million in revenue while building a global team of 250.

BigMachines was acquired by Oracle in 2013 for over $400 million. After this successful exit, Godard stepped down as CEO in 2011 and took time off to pursue two goals: playing a scratch round of golf and qualifying for the Boston Marathon. As of April 2013, he’s accomplished both. Born in Germany, but raised and educated in the US at MIT and Stanford, Godard is an odd combination of a laid back German and determined, precise American engineer. While his coding skills are rusty, he once wrote a simulation program at MIT that ran on a Cray.
Shradha Agarwal Co-Founder, Outcome Health // Chicago Ventures EP
Shradha Agarwal

Shradha Agarwal

Co-Founder, Outcome Health // Chicago Ventures EP

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ContextMedia Co-Founder Shradha Agarwal has a lifelong passion for people and communication, having started her first media enterprise when she was nine years old. At ContextMedia, Agarwal developed expansion initiatives that has doubled the company’s growth year-over-year. As an investor through Jumpstart Ventures and as a mentor, Agarwal is inspired by ambitious solutions to educate youth, mentor confidence in women and engage peers civically. Agarwal was honored as a Champion of Change by the White House and has won Tech Woman of the Year in Chicago.
Rob Chesney COO, Trunk Club // Chicago Ventures EP
Rob Chesney

Rob Chesney

COO, Trunk Club // Chicago Ventures EP

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As a former Vice President at eBay and Executive in Residence at Greylock Partners, Rob has deep e-commerce expertise and experience leading new businesses through periods of hyper-growth. As COO, Rob plays a central role in the general management of Trunk Club, overseeing customer acquisition, leading innovation of the technology platform and managing the build-out of the company’s operations. Rob holds an MBA from Kellogg and and a BA from McGill University. He looks forward to taking his son to a Cubs World Series game… before his son grows up.
Jason Duboe VP Special Projects, Outcome Health // Advisor
Jason Duboe

Jason Duboe

VP Special Projects, Outcome Health // Advisor

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Jason Duboe was a founding member of the Chicago Ventures team and led investments in enterprise software and healthcare IT from 2013-2017. He is now VP of Special Projects at Outcome Health.

His investments include PreparedHealth, CredSimple, Data.World, Datica Health, eRelevance, G2 Crowd, GAN Integrity, Get Smart Content, Healthfinch, Hint Health, infinite IO, ItemMaster, MyAlerts, PartsMarket, preData, PulseData, project44, Spotlite, Telnyx, Troops, WiderCircle, and XOR Data Exchange.

Prior to joining Chicago Ventures in June, 2013, Jason worked at Summit Partners, an $18bn venture capital firm, focusing on internet, software, and communications technology investments. Jason sourced and was actively involved in several of Summit’s technology portfolio companies. His investment experience includes minority growth investments in Logi Analytics (business intelligence and analytics SaaS), Zenoss (open-source IT systems management tools), and Acacia Communications (NASDAQ: ACIA). Jason is also an active angel investor and sales advisor to several early stage technology startups.

Jason holds an A.B. in Economics, with Honors, from Harvard University. He is a Chicago native and was named Forbes 30 under 30 Venture Capital in 2017.
Bob Fealy Founding Managing Director, Limerick Investments // Chicago Ventures Advisor
Bob Fealy

Bob Fealy

Founding Managing Director, Limerick Investments // Chicago Ventures Advisor

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Bob is founding Managing Director of Limerick Investments, a seed-early stage investment firm that empowers exceptional entrepreneurs to pursue emerging ideas and markets applying disruptive strategies and technologies. For over two decades, he has been involved with early stage technology companies, having founded Duchossois Technology Partners and serving as Chairman of the Illinois Innovation Accelerator Fund (i2A Fund) and Chicago Ventures. His past board seats include the boards of Alereon Semiconductor, NetEffect (acquired by Intel), Aura Communications (acquired by Freelinc), Continental Community Holdings (sold to private investment group), Chairman of AMX Corporation (acquired by Harman International) and Chairman of Milestone AV Technologies (acquired by The Pritzker Group). From 2001, he served as Chairman of Brivo Systems, which was sold in 2015 to an entity controlled by Dean Drako, founder of Barracuda Networks.

In 1986, he co-founded Chicago’s first Chinese-American Bank, New Asia Bancorp, which became one of Chicago’s largest minority owned businesses, and which was acquired in 2006 by Cathay General Bancorp. He currently is a member of the Board of Directors of Churchill Downs, Inc. (NASDAQ: CHDN), where he Chairs the Nominating and Governance Committee and serves on the Strategy and Executive Committees, and he is Lead Director of Pella Corporation. In 2014, Fealy co-founded with his daughter Live Grit Multisport, Chicago’s “Endurance Athlete and Triathlon Center” in the West Loop. He is a founding board member and Chairman of the Illinois Venture Capital Association and is a member of its Political Action Committee. He was awarded IVCA’s 2010 Richard J. Daley Medal for his contributions to the Illinois venture capital and private equity community.

Fealy previously served as President and Chief Operating Officer of The Duchossois Group, a privately-owned diversified operating and investment firm. Prior to Duchossois, he was Vice President – Business Strategy of Cummins, Inc., where his responsibilities included the establishment of various global alliances, acquisition and divestiture activities, and oversight of the Company’s minority investments in various technology ventures.

His current not-for- profit work includes serving as Chairman of the Board of Trustees of the University of Cincinnati Foundation, Chair of the Board of Directors of the Chicago Children’s Choir, board member and co-chair of the capital campaign of The Morton Arboretum, a partner in Social Venture Partners, an Advisory Board member of the Polsky Center for Entrepreneurship and Innovation at the University of Chicago Booth School, and a member of the University of Cincinnati Lindner College of Business Advisory Council, which awarded him the 2009 Carl H. Lindner Award for Outstanding Business Achievement. Fealy holds a bachelor’s degree from the University of Cincinnati Lindner College of Business. He was awarded an Honorary Doctor of Commercial Science degree from the University in 2013 and he is a certified public accountant (inactive), as well as a member of the Economic Club of Chicago, the Executives’ Club and the National Venture Capital Association.
Chris Hill Founder, Spotlite // Chicago Ventures EP
Chris Hill

Chris Hill

Founder, Spotlite // Chicago Ventures EP

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Chris Hill is a serial entrepreneur and active angel investor. Chris founded Spotlite in 2012 to provide consumers with the education and guidance to make health benefits decisions that best fit their personal needs. In 2014, Spotlite was acquired by Rally Health (owned by UnitedHealth Group). Chris founded PerkSpot in 2006 and currently serves as its Chairman. PerkSpot provides employee perks and buying programs to more than 5 million employees from large employers including Starbucks, Yahoo!, Southwest, and Walgreens. Before becoming an entrepreneur, Chris spent five years working in investment banking and private equity. Chris is a graduate of Taylor University.
Brett Hurt CEO AND CO-FOUNDER, DATA.WORLD // CHICAGO VENTURES EP
Brett Hurt

Brett Hurt

CEO AND CO-FOUNDER, DATA.WORLD // CHICAGO VENTURES EP

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Brett is the CEO and Co-founder of data.world, a new stealth venture that will very positively impact the world. He is also a seed-stage investor at Hurt Family Investments (HFI) in partnership with his wife, Debra. HFI are involved in 42 startups and ten VC funds. HFI has directly made 32 startup investments, and Brett has also joined the Advisory Board of ten additional companies. Prior to HFI, Brett founded Bazaarvoice (NASDAQ: BV) and served as CEO and President for 7½ years, leading the company from bootstrapped concept to almost 2,000 clients worldwide and through its successful IPO. He subsequently guided the company through a successful follow-on offering and two acquisitions, PowerReviews and Longboard Media. Prior to Bazaarvoice, Brett founded Coremetrics and helped grow the company into a global, leading marketing analytics solution for the eCommerce industry before its acquisition by IBM.

Brett holds an MBA in High-Tech Entrepreneurship from The Wharton School at the University of Pennsylvania and a BBA in Management Information Systems from the University of Texas at Austin. He serves as an Entrepreneur-in-Residence at the Wharton School. Brett previously served as an Entrepreneur-in-Residence at the McCombs School of Business and also served on the Board of Directors of Shop.org for six years. Brett established the Bazaarvoice Foundation and is very active in the philanthropic arena. He received the Austin Entrepreneurs Foundation’s Community Leadership Award in 2012. Brett is entrepreneur empowerment group RISE’s Serial Entrepreneur of the year for 2012. He was named by E&Y as Entrepreneur of the Year for Austin in 2009 and is a member of the Austin chapter of the international Young Presidents’ Organization (YPO). Brett was named CEO of the Year for large companies by the Austin Business Journal in 2012 and received the Joseph Wharton Award for Young Leadership in 2013. Brett and Debra received the LBJ Humanitarian Award in 2014 for their dedication to public service, philanthropy, and the Austin community. Brett was awarded the Henry Crown Fellowship from The Aspen Institute and joined the 2015 XIX class, named “Dare, Greatly”.

To help support Austin’s entrepreneurs, Brett serves as a Partner at Capital Factory and Mentor at Techstars Austin; invests in early-stage companies, funds, and philanthropic endeavors with Hurt Family Investments; serves as the Chairman of the Board at Edgecase (formerly named Compare Metrics); and blogs at Lucky7.io. He serves on the Board of Directors of the Entrepreneurs Foundation of Central Texas as well as Conscious Capitalism, both of which are non-profits designed to bring out the best in business in the way it can serve society at large. Brett can be followed on Twitter at @databrett.
Eric Lunt Chief Technology Officer, Signal // Chicago Ventures EP
Eric Lunt

Eric Lunt

Chief Technology Officer, Signal // Chicago Ventures EP

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Eric is the Chief Technology Officer of Signal (formerly BrightTag). Prior to joining Signal, Eric was co-founder and CTO of FeedBurner, which Google acquired in 2007. After the acquisition, Eric remained at Google in a senior technology role. Prior to FeedBurner, Eric co-founded and served as CTO at Spyonit.com (acquired by 724 Solutions), served as lead technical architect at Digital Knowledge Assets (creators of the collaborative personal publishing software “sceneServer”), and helped to lead the application architecture team in Accenture’s next generation technology group known as “Project Eagle.” Eric graduated from Princeton University with a B.S.E. in Mechanical Engineering and a Certificate in Applied Computational Mathematics. Eric was recognized as one of Crain’s Tech 25 for his contributions to drive technology growth in Chicago
Rishi Shah CEO, Outcome Health // Chicago Ventures EP
Rishi Shah

Rishi Shah

CEO, Outcome Health // Chicago Ventures EP

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Rishi U. Shah, Chief Executive Officer and Founder of ContextMedia, is a successful media and technology entrepreneur & investor who founded ContextMedia in 2006 to improve health outcomes by serving actionable health information to chronic disease patients. Today, the company’s digital place based media networks and mobile media offerings impact hundreds of millions of patient visits across 10,000+ hospital & health systems and the firm’s clients include 33 of the 35 largest life science manufacturers.

In addition to his work at ContextMedia, Rishi serves on the Board of Directors of many civic organizations including Young Presidents Organization (YPO), 1871, MATTER, and the Academy for Global Citizenship, an internationally renowned charter school. In 2012, he co-founded a personal venture investment firm, Jumpstart Ventures, through which he has made over 45 direct investments in fast growing early to late stage startups. Additionally, Rishi serves as a mentor for numerous technology start-up accelerator/incubator programs including TechStars Chicago, HealthBox and Blueprint Health in New York City.

Previous to ContextMedia, and while in his first year in college, Rishi founded NBR, a Northwestern University-based collaborative publication distributed to more than 60 leading college campuses worldwide. In high school, he founded a home computer consulting firm whose clients were acquired by a national electronics retailer. Rishi has also started and led several non-profit initiatives including the Urban-Suburban Domestic Exchange Initiative, a program sponsored by the Gates foundation to facilitate cross-school interaction.

Crain’s Chicago Business recognized Rishi as the youngest ever member of their annual 40-Under-40 class in 2009 and he frequently lectures at Northwestern University’s Kellogg School of Management & McCormick School of Engineering. A Chicago resident, Rishi is an avid fan of his hometown Bulls.
Jai Shekhawat CEO and Co-Founder, Fieldglass // Chicago Ventures EP
Jai Shekhawat

Jai Shekhawat

CEO and Co-Founder, Fieldglass // Chicago Ventures EP

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Mr. Jai Shekhawat co-founded Fieldglass, Inc. in 1999 and was its Chief Executive Officer. Under Mr. Shekhawat’s leadership, the Fieldglass platform has grown globally with users in 100+ countries, multiple languages and currencies and over $25 billion in annual spend.

Mr. Shekhawat served as Strategy Consultant of McKinsey & Co., where he served clients in the financial services, technology, corporate strategy, cross-border alliances, e-commerce, internet services and transportation industries, working primarily in the areas of corporate strategy, sales effectiveness, marketing and cross-border alliances. Mr. Shekhawat served as Head Of Operations of Syntel, where he helped build it from a 50-person firm to nearly 700 consultants in six years and also helped create an international sales and service delivery organization to provide application management services to the Global 2000.

He has more than 18 years of experience with software development, information technology and management consulting. Mr. Shekhawat spent several years as a senior executive in the Information Technology field. Mr. Shekhawat also co-founded Quinnox. He serves as a Director of Quinnox, Inc. He serves as Members of The Board Of Advisors at StarVest Partners, L.P. He serves as a Member of Advisory Board of Eved, L.L.C.

He is a Founding Member of both the FireStarter Fund and the Chicago TiE chapter. He is a Mentor within the Chicago entrepreneurial community. He serves on the Board of Trustees of the Field Museum of Chicago and is a Board Member of Metrosquash. He has held various civic and board positions including serving on the Mayor’s Council of Technology Advisors (MCTA) for the City of Chicago, and the board of TiE Midwest. He is actively involved with the University of Chicago’s Booth School of Business and his alma mater, Northwestern’s Kellogg School of Business, in a variety of ways. He is a frequent speaker at a variety of industry forums. He was named Ernst & Young’s “Entrepreneur Of The Year(R)” in the private equity/venture capital category for the Midwest region. He was Ernst & Young’s 2012 Midwest “Entrepreneur of the Year” as well as the 2012 recipient of the Peter Yessne Staffing Innovator Award, recognized for pioneering the Vendor Management Software (VMS) space.

Mr. Shekhawat holds Master’s in business administration with specializations in finance and strategy from the J.L. Kellogg School of Management at Northwestern University in Evanston, Ill. He holds Bachelor’s Degree in Management Science from the Birla Institute of Technology and Science, Pilani, India.
Brian Spaly Founder and CEO, Trunk Club // Chicago Ventures EP
Brian Spaly

Brian Spaly

Founder and CEO, Trunk Club // Chicago Ventures EP

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Brian is currently the Founder and CEO of Trunk Club, where he’s focused on making it easy for men and women to discover and acquire awesome clothing without the hassles of the traditional shopping experience. Trunk Club has clubhouses in Chicago, Dallas, Washington D.C., Los Angeles and Manhattan, and a direct sales team of over 500 personal stylists. Nordstrom (NYSE:JWN) acquired Trunk Club in 2014 for $350M.

Prior to leading Trunk Club, Brian founded Bonobos, a men’s clothing company that is famous for the best-fitting pants on earth, by selling trousers out of the trunk of his car during business school in Palo Alto.

Today Bonobos is a thriving ecommerce/hybrid business based in Manhattan with over 20 showrooms in top cities across America and $100M+ revenue run rate. He serves on three startup company boards, including Shiftgig, Blitsy and Luxury Garage Sale. As well, he is a prolific private investor and advisor to entrepreneurs, with a personal portfolio of 50+ angel investments.

Brian holds an MBA from Stanford and an AB degree from Princeton. He is an avid hockey player, cyclist, telemark skier, squash player, and enjoys windsurfing, sailing and water skiing. His favorite authors are Roald Dahl, Neal Stephenson, Mark Helprin, and Nicholas Taleb.
Sam Yagan Vice-Chairman, Match Group // Chicago Ventures EP
Sam Yagan

Sam Yagan

Vice-Chairman, Match Group // Chicago Ventures EP

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Sam Yagan is the Vice-Chairman of Match Group (Nasdaq: MTCH), a position he assumed after serving as the company’s Chief Executive Officer and leading it through a period of explosive growth that culminated in its IPO. He has co-founded several companies, including SparkNotes, eDonkey, OkCupid, Techstars Chicago, and, Firestarter Fund, & Corazon Capital.

Sam has been a leader in the dating industry since he co-founded OkCupid in 2003 and grew it into one of the most popular dating products in America, amassing over four million active users. OkCupid has earned widespread media acclaim and has been described as “the Google of online dating” and where “dating meets Facebook.” In 2011, Match, Inc. acquired OkCupid for $90 million.

Sam’s prior entrepreneurial ventures in the consumer internet sector include SparkNotes (founded in 1999), still the dominant brand of study guides and eDonkey (founded in 2002), once the largest P2P file-sharing network in the world. He sold SparkNotes to Barnes & Noble, Inc., where he served as Vice-President and Publisher and oversaw the expansion of the previously all-digital brand into an expansive multi-platform media business.

Outside of work, Sam’s primary passion is working with early-stage entrepreneurs. In 2009, he co-founded Excelerate Labs (now TechStars Chicago), a leading start-up accelerator, and served as its first Chief Executive Officer. In 2014, Sam founded Corazon Capital, a small angel fund; he sits on the board of several start-ups, including ShiftGig, SpotHero, Roniin, & Brilliant. He also advises several venture capital funds, including Hyde Park Venture Partners and the FireStarter Fund, which he co-founded. He serves on Target Corp’s Digital Advisory Council and the Stanford Graduate School of Business Management Board.

Sam has been named to TIME Magazine’s “100 Most Influential People in the World,” Fortune Magazine’s “40 Under 40,” Crain’s Chicago “40 Under 40”, Billboard Magazine’s “30 Under 30,” Crain’s “Tech 25,” D Magazine’s “Dallas 500” and ranked #19 on Silicon Alley Insider’s “Most Inspiring and Influential People.” He has received the Chicago Innovation Awards’ “Visionary of the Year Award,” IMSA’s “Distinguished Leadership Award,” and the DCIA’s “Pioneer’s Award.” Sam has testified before the Senate Judiciary Committee and has spoken at the CATO Institute, Digital Hollywood, IRCE, the Federal Trade Commission, and numerous other industry events.

Sam has a BA with honors in Applied Mathematics and Economics from Harvard College and an MBA from the Stanford Graduate School of Business, where he earned distinction as a Siebel Scholar, an Arjay Miller Scholar, and the Henry Ford Scholar, the award granted to each class’s valedictorian.

We’re seed stage tech investors.

That’s why we’re here.

Investment focus

Our team

Investment Committee