Brad Keywell

That gamble paid off as Keywell went on to found or co-found a series of highly successful firms, including Groupon, the wildly popular group buying daily deal website that allows members to collectively take advantage of reduced prices on everything from local yoga classes to resort stays in Florence, Italy. He is also a co-founder and director of MediaBank LLC, a firm providing integrated technology platforms and solutions to the advertising and media buying industry. In addition, he is co-founder and managing partner of Lightbank, a venture fund investing in disruptive technology businesses. That term – disruptive technology – is defined as something that creates a new market, helping improve a product or service in unexpected ways.

Disruptive technology “on a daily basis gives us the opportunity to create things that never existed before,” Keywell says. “Today’s technology allows for true creation. It allows us to create businesses that could never have existed before now. It’s an exciting reality, harnessing this amazing technology.”

Bridging that gap between business and technology is part of what drives Keywell’s entrepreneurial goals. There is also the simple fact that “I find the act of creating new businesses makes me happy.” There is also the knowledge that with each new business comes a new opportunity to create jobs and improve lives. “New jobs will save the country,” he says.

Cranbrook, Keywell says, “gave me a sense of where and who I was . I look at it as a time when I was able to explore my creative side. It was an exceptional and formative time of my life. There are lucky people in life who get to go to a school that helps you know who you are. Cranbrook did that.”

Keywell works to help younger people find their path, through mentoring programs in the Chicago schools and as an adjunct professor at the University of Chicago Booth School of Business. For those thinking of becoming entrepreneurs themselves, Keywell advises, “It’s like being an artist. Artists have to create art whether it’s good or bad, whether it’s commercially successful or not. They have an insatiable need. Entrepreneurs have that need, too.” But, he says, it is important to remember “that a lot of it is failure. You have to work through failures to find those successes. Most overnight successes are 20 years in the making.” But for those working in this age of technological wonder, those successes can be well worth the wait.

The digital world may never be a perfect place but it will continue to evolve in ways that are unimaginable to most of us today. And we will rely upon visionaries such as Adelson, Westergren, Schwartz, Krstic and Keywell to explore that world’s frontiers, paving the way for the rest of us to follow. In an industry that never stands still, it is a relief to know it will never lose its intellectual appeal, constantly enticing innovators to keep pushing its ever expanding borders.