Kevin O’Leary is a Canadian businessman who appears as one of the Main Sharks on Shark Tank. O’Leary has been on every season of Shark Tank.
O’Leary acquired his fortune by selling his educational software company in 1999 to Mattel, a company best known for making toy cars. In 2006, O’Leary joined Dragons’ Den, the Canadian analogue of Shark Tank. In 2009, O’Leary left Dragons’ Den to join the US version of Shark Tank. Since joining Shark Tank, O’Leary has also become known for running in the 2017 Canadian election for leadership of the Conservative Party. O’Leary dropped out of the election while still a frontrunner, because he felt that his lack of support in Quebec would make it difficult for him to challenge Justin Trudeau, the current Prime Minister, in 2019.1
O’Leary has written three books: Cold Hard Truth: On Business, Money & Life, The Cold Hard Truth on Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, and Cold Hard Truth on Family, Kids and Money.
Personality on Shark Tank
O’Leary is the Shark who most personifies the “Shark” image on Shark Tank. He has a reputation for playing hardball when making deals, and he often comes into deals after other Sharks have already decided not to make an offer. His offers are often structured as loans with aggressive interest rates. On Season 1 of Shark Tank, after a particularly aggressive offer, Barbara Corcoran sarcastically referred to O’Leary as “Mr. Wonderful”. O’Leary quite liked his new nickname, and the name stuck. While all Sharks are interested in learning about entrepreneurs’ financial statistics, O’Leary tends to be much more focused on finances than other Sharks when questioning entrepreneurs. Despite O’Leary’s aggressive business persona, he comes across as likable on the show. He is blunt, but rarely says anything ignorant, and when he acts silly on the show, it comes across as funnier than other Sharks due to the contrast with his shark-like demeanor.