Millionaire Kevin “Mr. Wonderful” O’Leary of the popular TV show Shark Tank, is probably its most recognized cast member after billionaire Dallas Mavericks owner Mark Cuban. O’Leary’s no nonsense, hard-nosed negotiation approach and acerbic wit have made him the perfect foil to the other, more diplomatic millionaire investors. 

Apart from his support of entrepreneurism and savvy investments, O’Leary is generous with advice through his explanations of motives and decisions made over the course of doing business. His YouTube channel highlights a number of these pearls of wisdom, and one episode, in particular, cited his top tips that changed his life and set him on his present course.

No More Checks

O’Leary’s first major lesson came from his mother while he was attending college. She told him that once he graduated, she was cutting off his support payment checks and would be on his own. While the first post-graduate years were a struggle just to make rent, O’Leary managed to survive, thrive, and succeed, but he admits that he would not have honed his entrepreneurial skills if he still had that safety net. He has imparted that same principle towards raising his own children and his grandchildren. O’Leary strongly believes that coddling kids instead of letting them leave the nest cleanly can be the “worst cure” for them, as it stunts their growth potential to think on their own and how to cope in the world with strength and independence.

Experience Trumps Education

While nearing graduation with his classmates and filled with bravado over how they would be conquering the world with their freshly minted sheepskins, a guest lecturer at his college threw ice cold water on their fervor. He declared that only a handful of them would be successful, some would be total failures, and two-thirds of them would wind up getting regular jobs and making a living in another field.  He also stated that experience was more important than education, and the longer they worked at something, the smarter they’d become, vs. what they thought they knew from college.

O’Leary credits this revelation with how he developed his own instincts and gut call decision-making ability, which he claims has been accurate nearly 99% of the time – all thanks to the experience he has developed in starting, building, and selling businesses of all types.

Stepdad’s Broader View

O’Leary’s aspiration as a student was to become a photographer or filmmaker. However, he admits to not knowing anything about those industries at the time, and that he was aware of others in his own circle who were more talented than him. His stepfather, noticing O’Leary’s dilemma, suggested that he go for a Master’s degree in business, which would give him a perspective on how to approach any field. 

This proved invaluable for O’Leary’s first business, which was producing video shorts for hockey teams. The business became so successful that it attracted the attention of a larger production company that offered to buy them out. O’Leary and his partners made a handsome profit, and his path was set.

Shark Tank and the Spirit of Entrepreneurism

The appeal of Shark Tank, which is a US spinoff of the UK TV show, Dragon’s Den, is that it celebrates the entrepreneur, who gamely defies the odds and is willing to take on the risk of failure to serve a dream. Fans root for the underdog and cheer their success. O’Leary’s tough talk, down and dirty experience is the jolt of reality that many entrepreneurs require to adjust their game plans to realize those dreams. 

 

 

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