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Brad Keywell

The Mindset of a World-Class Entrepreneur


In this episode

Randall Kaplan is joined by Brad Keywell to discuss what it takes to achieve excellence at the highest level as an entrepreneur. In this episode, Brad shares with listeners how to out-work and out-hustle the competition, why he channels his entrepreneurial drive into disrupting industries, how he grew Groupon from 124 employees to 5,100 employees in a single calendar year, and much more.

Topics Include:

Brad’s five keys to success.  Brad’s early business ventures, including a greeting card business he started at age six.  The power of preparation.  Brad’s mentorship under Sam Zell.  The lasting influence of loving, supportive parents.  Tangible versus intangible skills.  Fundamental truths about parenting.  Working with the energy of fear.  Choosing business ventures as an entrepreneur.  Overcoming early failures.  Focusing on what you can control.  Balancing individual needs and collective needs.  Mental health, self-care, philanthropy, and other topics.

Brad Keywell is an incredible entrepreneur who has co-founded a variety of companies including Echo Global Logistics, Enterprise Transportation, Uptake, and most famously Groupon. He is currently the CEO at Uptake, which reached the $2 billion valuation faster than any other tech company in history - and was a Co-Founder of Groupon, which at the time reached the $1 billion valuation faster than any other company in history. In 2019, Brad received the Ernst & Young World Entrepreneur of the Year Award, becoming one of only three American winners in the award’s 21-year history. He is the co-founder of Lightbank, a venture capital firm with $360 million under management that specializes in making venture capital investments in "disruptive" technology companies in the United States. Brad is also the founder of Chicago Ideas Week, a week-long conference bringing together thought leaders and innovators from around the world to speak on a variety of topics - and he has also signed The Giving Pledge, promising to give away at least half of his wealth to charitable causes.



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