Kevin O’Leary, famous for his appearances on Shark Tank, started his journey to business success because of two girlfriends.
You might know Mr. Wonderful from Shark Tank. To jog your memory, he’s the bald guy always swindling entrepreneurs into licensing and royalty deals. Kevin O’Leary made his fortune from building The Learning Company, a software company that made computer programs and games that helped kids improve their reading and math scores. But his journey becoming Mr. Wonderful started long before that.
It was in high school that he caught the entrepreneurial bug. In 11th grade, Kevin was into a girl in his class. She worked at a shoe store in the mall. To close the gap, he applied to a job as a scooper at the ice cream shop right across from her store (bold move, Kev). Not too long into his ice cream scooping career, Kevin’s boss told him to scrape the gum off the floor of the store (when taste-testing different flavors, people would always take out their gum and throw it on the ground—gross) He refused. He was a scooper—not a scraper. Plus, what if his crush saw him peeling gum off the floor? No way he’d get a date after she saw that. O’ Leary was fired on the spot and swore to himself that he’d never work for anyone but himself from there on out.
The transformation into Mr. Wonderful had begun.
In college, he majored in psychology and environmental science. He was also chasing tail again. His girlfriend led him to attend a cinematography night class. And thus began his love for the camera. A couple years later, he pursued his MBA (because, as impressive as his double major was, there's not much demand for plant whisperers). He convinced the grad school to pay him to make a documentary to use for prospective students. The school gave him $30,000. He built out a team. The documentary was a hit, and they decide to make a company after college. They were good at what they did. After 2 years, they sold Special Events Television for hundreds of thousands of dollars.
He didn't end up with either of the women, but they definitely fueled the fire to become the Mr. Wonderful he is today. How's your love life? It might just end up being the focal point of your own Freshly Squeezed story.
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