Kevin O’Leary, also known as Mr. Wonderful, is one of the original Shark Tank sharks who, since 2009, has made the dreams of some entrepreneurs come true and sent others home in tears. The 17th season premieres in about two weeks, and if my conversation with him for our show, How Success Happens is any indication, time has not mellowed this man.
He calls b.s. when he sees it, but he isn’t a hater. As fast as O’Leary is to declare “I’m out!” he also doesn’t hesitate to throw his full energy behind the things he loves. If you follow Mr. Wonderful on social, you know he loves watches. WORSHIPS watches. We talked about where his passion for collecting rare timepieces came from and how that obsession led to his latest venture, WonderCare, a partnership with the 1916 company.
We also talked about the one investment his wife told him he was “out of his mind” for making (a record-setting winning $12.9 million auction bid on a basketball card,) his thoughts on management tactics, how he keeps his energy up, and the worst mistake he sees people make over and over again in entrepreneurship.
You can watch our entire conversation above or listen here, and check out below for some truly wonderful highlights.
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Give the Crap a Rest
The number one thing hurting most entrepreneurs’ ability to stay focused and energized? “Shit food,” says O’Leary. “You don’t know how bad that crap is for you until you stop eating it, and then you feel incredible.” He tells anyone he meets to try the Yuka app, which scans barcodes of packaged foods and tells you if you really want it in your body or not. He also stresses exercising your mind by doing things out of your comfort zone. “The producers of the upcoming film Marty Supreme called me and said, ‘Look, we’ve got a part in a movie for you and we’re looking for a real asshole and you’re it.'” O’Leary has never done scripted entertainment before and jumped at the challenge.
Takeaway: If you want to stop feeling like garbage, stop eating garbage.
Great Customer Service = Great Profits
Responding to a listener question about maintaining margins, O’Leary offers: “Customers covet one thing more than anything, service and support. …If the minute they call you, you fix it that same day… they’re not going to quibble about the bill.” He compares this to Apple’s ecosystem: “I worked for Steve Jobs way back in the early ’90s. Not a nice guy, but he taught me so much. He said, ‘I don’t need to do market research. They don’t know what they want till I tell them what they want.’ I said, ‘Steve, you sound like such an asshole.’ But he was right. He said they want a great product with fantastic service.”
Takeaway: Superior service commands demand—invest in happy customers, not endless discounts.
Success Demands Resilience, Not Certainty
Mr. Wonderful warns founders against falling in love with their own projections: “The road to success in entrepreneurship is a journey, it’s not a destination… Stuff you never saw coming at you, boom, it hits you. You need to be flexible.” He values founders who own their failures: “When you fail, it’s your fault. You screwed up. Own it and learn from it and don’t do it again. Then you get me to invest in you.”
Takeaway: Build flexibility into your business and see failures as critical learning opportunities.
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Christopher Willard | Getty Images
Kevin O’Leary, also known as Mr. Wonderful, is one of the original Shark Tank sharks who, since 2009, has made the dreams of some entrepreneurs come true and sent others home in tears. The 17th season premieres in about two weeks, and if my conversation with him for our show, How Success Happens is any indication, time has not mellowed this man.
He calls b.s. when he sees it, but he isn’t a hater. As fast as O’Leary is to declare “I’m out!” he also doesn’t hesitate to throw his full energy behind the things he loves. If you follow Mr. Wonderful on social, you know he loves watches. WORSHIPS watches. We talked about where his passion for collecting rare timepieces came from and how that obsession led to his latest venture, WonderCare, a partnership with the 1916 company.
We also talked about the one investment his wife told him he was “out of his mind” for making (a record-setting winning $12.9 million auction bid on a basketball card,) his thoughts on management tactics, how he keeps his energy up, and the worst mistake he sees people make over and over again in entrepreneurship.
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