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Most tech entrepreneurs might dream of ending up with their companies listing on the Nasdaq, but Brad Keywell isn't sure it's always the right call to make.

Doing an IPO ‘can be fun’ but doesn’t always lead to the best result

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Chicago tech veteran Brad Keywell just became the third U.S. founder to win the EY World Entrepreneur Of The Year award.

Uptake CEO Brad Keywell Wins World Entrepreneur Award

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Brad Keywell has been named the EY World Entrepreneur of the Year for 2019, marking a record third win for the US in the competition’s 19-year history.The serial entrepreneur, also known for co-founding voucher website Groupon, was recognised for building Uptake Technologies, a maker of AI software for industrial companies.

AI software founder wins world entrepreneur award

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Brad Keywell is cofounder and CEO of Uptake, an industrial AI startup that achieved unicorn status in its latest funding round. In a recent video interview with LinkedIn managing editor Chip Cutter, Keywell revealed that there's a very specific ritual he partakes in every Sunday night — one that makes a big difference to his employees and also his family.

This successful CEO says his Sunday ritual keeps his employees more in tune and makes his week more productive

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Uptake's mission: to create a world that always works. That's a pretty big ambition, but this Chicago-based SaaS start-up believes that AI and machine learning are the answer. Uptake takes voluminous amounts of data produced in industries like energy and transportation and uses AI to unlock all the ways a particular process or machine could potentially fail.

Uptake named CNBC Disruptor 50 company

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When you're one of three founders of Groupon, the company that energized Chicago's tech scene, what do you do with the rest of your life? If you're Andrew Mason, you head for the West Coast. If you're Eric Lefkofsky and Brad Keywell, you stay in Chicago and start more companies, fund others with a VC firm, and get involved in Chicago's civic and philanthropic community.

Life after Groupon: Eric Lefkofsky and Brad Keywell

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Earlier this week, I wrote that the two questions I get most frequently from people who are interested in learning about Heartland Tech are about what cities they should be watching and what startups should be on their radar. I wrote about cities to watch here, and now I’d like to talk about startups to keep an eye on in 2018.

10 startups outside Silicon Valley to watch in 2018

When we think about corporate philanthropy—the allocation of company resources for public benefit—we often limit our definition of resources to employee time, money, and product. But how valuable are these resources, actually, to social sector organizations?

Giving Your Genius: A New Approach to Corporate Philanthropy

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The world is changing. There’s no way around this fact. The Fourth Industrial Revolution is now. And, whether you know it or not, it will affect you. Billions of people and countless machines are connected to each other. Through groundbreaking technology, unprecedented processing power and speed, and massive storage capacity, data is being collected and harnessed like never before.

The Fourth Industrial Revolution is about empowering people, not the rise of the machines

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Brad Keywell is enjoying a repeat act. In the short period of time since he co-founded Chicago-based Uptake Technologies in July 2014, Keywell has seen his start-up reach a $2 billion valuation on the back of $146 million in funding, including $40 million from Revolution Growth, the venture firm of AOL co-founder Steve Case.

Why Warren Buffett is betting on this software start-up

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Given there are only 24 hours in a day, it doesn’t seem possible to do everything Brad Keywell does.  For starters, the Detroit-area native co-founded Groupon.  But there’s more: He’s created multiple other companies that have had a profound influence on Chicago, including Tempus, a technology company working to battle cancer; Lightbank, a venture fund investing in technology businesses; and MediaOcean, a technology platform for the media-buying industry.

Men Of The Year

Brad Keywell is the co-founder of Uptake Technologies, Lightbank, and Groupon, and has launched over a dozen companies. But don't call him a Silicon Valley darling -- he's committed to seeing Chicago rise as a tech hub. Produced by Haley Draznin, CNN.

Brad Keywell: The Ultimate Entrepreneur

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It’s been nearly two years since Fortune profiled entrepreneur Brad Keywell’s startup, Uptake Technologies, which slices and dices data from sensors on industrial machinery and other sources. Since then, the Chicago-based company has done some growing up.

Exclusive: Berkshire Hathaway Energy Inks Deal With Data Crunching Startup

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Every successful business begins its life as an idea. The exhilarating journey from idea to reality is the essence of the entrepreneurial endeavor--and yet, most ideas never complete this journey. For every idea that triumphs, there are a thousand that fall by the wayside. As someone who believes that human innovation and entrepreneurial action is among our highest callings, I constantly ask myself: How do I know if an idea will succeed?

The most important thing you can do with your brilliant idea is to try to kill it

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Uptake differs from other of Keywell’s co-founded start-ups in that he employs collaborative disruption: “We are disrupting the blind spots,” Keywell says. In other words, “We are choosing to be disruptive with a partner who has a strong edge, rather than what we’ve traditionally done – which is be disruptive from the outside.”

Uptake CEO Brad Keywell: “We are disrupting the blind spots”

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Caterpillar, the sixth-largest public company in the Chicago region, and Brad Keywell, one of the city's wealthiest venture capitalists, are teaming up on a new startup, called Uptake, the equipment-maker announced Thursday.