Kevin O'Leary, the outspoken investor known as “Mr. Wonderful” from Shark Tank, didn't always plan on being a business mogul. His first love was something completely different: photography.
Fresh out of high school, Kevin dreamed of turning his passion into a career. He even set up a lab in his basement and was doing everything he loved. But his father had a harsh dose of reality for him.
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"You're not good enough and you'll starve to death," his dad bluntly told him. His father pushed him to go to college and earn a degree, telling him not to follow his heart. This tough love turned out to be some of the best advice Kevin could have received, even though it might have felt like his aspirations were being dashed.
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Kevin took his father's advice and went to college, eventually earning an MBA. Though it wasn't part of his original plan, this degree would later be a game-changer. He soon found a way to merge his passion for photography and production with his business skills, launching his first company, Special Event Television, which produced programming for East Coast hockey games.
That first venture set the stage for a highly successful career. Kevin and his co-founders eventually sold the company and Kevin used the money to start his next venture, a software business called Softkey, which he later sold for $4.2 billion.
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Still in his mid-30s, Kevin decided to retire and live the kind of financially independent life that most of us can only imagine. He traveled the world, visiting the most beautiful beaches and other stunning locations. However, something unexpected happened – he found himself bored in spite of the luxury and endless travel. “I went to every beach on Earth,” he says, but after three years, “It was really boring.”
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The excitement of creating something, taking chances and participating in the business world was something he missed. Retirement proved unsatisfactory, even though it seemed like the ultimate goal.
Apart from his father giving him tough advice, Kevin also credits his mother for giving him some of the best financial advice he ever received. She taught him and his brother a simple but effective lesson: "Boys, never spend the principal, only the interest." Although he didn’t fully understand it then, this lesson has guided him throughout his life and career.
Kevin O'Leary's life story shows that success typically doesn't follow a straight line but often involves following difficult-to-hear advice.
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