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Serial Tech Entrepreneur Brad Keywell’s Secrets to Success


Take a look at the resume of Brad Keywell and it’s hard to imagine that these are the accomplishments of a single person. Anyone would be considered lucky to have just one of those career credentials under their belt. Based out of Chicago, Keywell has co-founded over 15 companies to date, including several high-profile tech startups such as Lightbank, Mediaocean, Echo Global Logistics, MediaBank and Groupon. Oh yeah, and he’s only 42.

“Grampa Fred” Kiesner first met Keywell back in the late 80s when he taught entrepreneurship at the University of Michigan. Keywell was just a freshman when he somehow managed to convince Kiesner to let him into his graduate-level entrepreneurship course.

“I saw a spark in this young kid and was impressed by his confidence and tenacity,” said Kiesner. “He went on to become one of the greatest entrepreneurs of our time and I am honored that he took the time to share his incredible story with our LMU students.”

During his lecture, Keywell spoke about his path to becoming a serial entrepreneur and shared some of the biggest challenges and lessons he’s learned from launching new business ventures. His started his first business, homemade greeting cards, at the tender age of six. By the time he graduated from the University of Michigan, he had already launched and sold several companies. During law school, he met current business partner Eric Lefkofsky, admitting “Eric and I were the only two from our graduating class who didn’t end up working in the legal industry.”

According to Keywell, the greatest characteristic an entrepreneur can possess is resourcefulness. Entrepreneurs must be willing to adapt to challenges and changes in the marketplace and find the right people who can help them achieve their goals. He also stressed the importance of having a mentor in your life. For him, that was media and real estate magnate Sam Zell.

Keywell somehow finds time in his busy schedule to be an adjunct professor at the University of Chicago Booth School of Business, where he teaches a course on entrepreneurship and building technology-based businesses. He is also the founder and chairman of Chicago Ideas Week, an annual event which hosts nearly 200 speakers at 80+ events with global media coverage, and is emerging as one of the major ideas and innovation conferences and platforms in the country.

Keywell received the 2011 Entrepreneurial Champion award from the Chicagoland Entrepreneurial Center.  He was named one of the nation’s Top Ten Collegiate Entrepreneurs in 1991 by the Association of Collegiate Entrepreneurs, and received the 2000 Conrad Hilton Distinguished Entrepreneur Award from Loyola Marymount University. He was named one of the “Internet 100” by Crain’s Chicago Business. He was keynote speaker at the 2004 National Conference of the Collegiate Entrepreneurs Organization. 

Keywell received his J.D. cum laude from the University of Michigan School of Law (1993) and his Bachelor of Business Administration with honors from the University of Michigan (1991). He also studied in 1990 at the London School of Economics. He is a member of the State Bar of Illinois and the Michigan Bar Association.