Brad Keywell

Uptake Technologies Co-Founder & CEO

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How Do You Come up With Your Best Ideas?

I get great ideas from actively finding inspiration and to me that often is people. People that I reach out to, to meet, I want to meet people that challenge me specifically in areas I don't…

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What Do You Splurge on in Your Business That's Worth It?

Well, we splurge on the basics, which is plentiful food, and drink, and creature comforts. We also splurge on education. So we splurge on exposing ourselves to interesting experiences and learning. So here's an example,…

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What Is the Secret to a Great Co-Founders' Relationship?

I've often said that having a business partner is every bit as challenging as having a spouse. Success in both of those is dependent upon communication. So by that I mean you have to be…

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How Do You Get Work Done While You Travel?

The way that I get stuff done when I'm, well anywhere, whether it's on the road or in my office, is about bucketing out those times and focusing. Focusing on the work at hand, and…

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How Do You Manage Your Emails?

I've tried every email management technique that can be imagined. I'm now a GTDer, so I'm big on the Getting Things Done methodology. I'm focused on quick touches, quick action, and the next action as…

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What Would You Do if You Found out You Had Two Weeks Left to on Earth?

If I had one last day on Earth, I would be with my family, of course, and I'd be with every friend I've ever had. And we would be learning, we would be learning and…

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How Much Money Does Your Local Movie Theatre Make?

First of all, the answer is not, so it's about how you figure out the answer. So, to me at least, it's the input which is the number of people, number of nights, number of…

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Describe the Internet to Someone Who Just Woke up From a 30-Year Coma.

The internet is every ounce of information ever accessible within four clicks. And then I have to explain what a click is so then we get to complication. So maybe I'd say the four things,…

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What Rituals Do You Perform Before a Stressful Task?

One hard task is working out. Whether it's running a marathon or it's just a workout, and the ritual there is just to be grounded. If there's a more pervasive ritual it's probably about presencing…

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How Do You Build a Strong Personal Brand?

The best way to build a brand, whatever the brand is, is to deliver value. And so whether it's a comedian who builds a brand by telling great jokes that make you laugh and they're…

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What Role Does Instinct Play in Your Decision-Making Process?

I'm a big believer about full-body instinct and so when somebody says my gut doesn't feel right, to me that matters. Where I can explain that it's used are really every decision about to start…

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Are Entrepreneurs Born or Can They Be Made?

I believe entrepreneurship is learned and I think that it is only learned through experience. So it is hard to truly learn the whole framework or playbook of entrepreneurship in a classroom or from a…

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Do You Have Any Tips for Managing Millennials?

Well, first of all, you're managing people that happen to be in a certain age bracket. But people, not matter what their age, I believe, want meaning in their lives, and they want to keep…

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How Are Millennials Different From Previous Generations Entering the Workforce?

There's a need to understand exactly why what somebody does matters. I think maybe in generations past someone would go work somewhere, do their job, and not really be exposed to or question why and…

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Where Do You Go to Rejuvenate?

To rejuvenate I go to the gym or I go for a run or I go, I move. So to me, rejuvenating is not about shutting down and doing nothing, rejuvenating is about leaning in…

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How Do You Make Meetings More Effective?

I think meetings are the ultimate double-edged sword. Let me explain, on the one hand you have to have meetings because it's about communication. On the other hand they're misused in every possible way. So…

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How Do You Overcome Imposter Syndrome?

I don't know exactly the imposter syndrome definition, but I would tell you that entrepreneur minds are active minds and a lot of the action is self-defeating. So the syndrome I think that is easy…

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How Do You Stop Procrastination?

Look, Adam Grant, who I'm friends with would tell you that great creative minds thrive on procrastination. I fall into periods of procrastination that turn out to be very helpful. Others that I'm frustrated by…

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What Is the Best Advice You’ve Ever Received?

One amazing piece of advice that stuck with me for 30 years now, is from Sam Zell, who's been a mentor to me for 30 years. And early in our relationship, what he explained to…

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What Is a Unique Challenge Faced by Women Entrepreneurs?

Well, I think that there's two challenges for female entrepreneurs. One is, how you're perceived, that's a challenge. But the other challenge is really, do you walk into a room thinking that you're being perceived…

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What's an Effective Perk to Attract Top Talent?

Well, the best of all perks is trust, trust that the person joining the team can do what they're being asked to do, trust that they have the resourcefulness to figure it out, to get…

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How Do You Keep Your Superstar Employees Happy?

The answer is, provide opportunity to matter. Yes, it's about making money and it's about upside. It's also about doing good work that's interesting and knowing that what you do has a important part in…

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What Are You Bad At?

I am, well, I'm not going to say bad. It is hard for me to really slow down. My, there's clarity, I suppose, at least in the business that we are in, it's an edge…

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How Much of Your Career Has Been Planned and How Much Has It Been Left up to Chance?

The plan of my career has been to not have specific plans. Meaning that the plan was, I knew what I didn't want to do, I also knew the essence of what I needed to…

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What’s Your Biggest Career Mistake?

As someone who is very vocal about embracing the word no and learning from no's I would say I've had many mistakes and I generally can look back on them as valuable. And in terms…

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How Do You Conduct a Post-Mortem?

Postmortems come in lots of flavors, and my flavor is being organized, so that you can pass on a map to the next travelers. So a postmortem to me is a checklist, whether it's the…

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What’s the Biggest Mistake When Raising Money?

People pouring their hearts into businesses that just don't have to exist. Saying, trying to convince others that it must exist is one story, having the knowledge that structurally or fundamentally in an industry, the…

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How Do You Meet Someone You Don't Know?

You meet someone that you don't know by reaching out to them, as simple as that sounds, whether it's placing a phone call, or sending a letter. Most people find that to be a paralyzing,…

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What Are Your 3 Must-Dos Everyday?

Every day I must take a walk. Every day I must meditate or have some mindfulness. Every day I must get stuff done.

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How Do You Handle Receiving Criticism?

I view honest feedback about how to be better as amongst the highest sources of valuable things I could say to somebody is clear feedback about how to be better, and I ask for the…

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If You Were Stranded on a Desert Island, What 3 Things Would You Want With You?

I would probably bring, well, I'd bring a great book, or maybe I'd bring a Kindle that was loaded with a hundred thousand great books, number one, I could knock out all the reading I'd…

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"Co-founded over 15 companies including Groupon and MediaOcean"

Brad Keywell is a Chicago-based entrepreneur with over 25 years experience building data-driven B2B enterprises. Prior to his current role as cofounder and CEO of Uptake Technologies, Brad cofounded over 15 companies, including Groupon, Echo Global Logistics and MediaOcean, as well as the technology startup venture fund Lightbank.

A Midwest native, Brad is a vocal advocate for the region's entrepreneurial and tech communities. He is founder and co-chairman of Chicago Ideas, the chairman of the Future Founders Foundation and formerly served as chairman of the Illinois Innovation Council. He has been recognized as an Entrepreneurial Champion by the Chicagoland Entrepreneurial Center and currently teaches a course at the University of Chicago Booth School of Business on entrepreneurship and disruptive technology.

Brad received a Bachelor of Business Administration with honors from the University of Michigan in 1991, and a J.D. cum laude from the University of Michigan School of Law in 1993.