Kevin O'Leary net worth: Kevin O'Leary is a Canadian entrepreneur, venture capitalist, investor, and television personality who has a net worth of $300 million. Kevin O'Leary has earned his net worth as the founder of a software company known as SoftKey International. The company was a publisher of personal computer software during the 1990s. The software was distributed on CD-ROM and was designed for use on Windows and Macintosh computers. O'Leary started the company with a $10,000 investment from his mother. From there, with the help of Gary Babcock and John Freeman, he started the company in the basement of his Toronto home. By 1994, Softkey had acquired more than sixty of its competitor's companies including WordStar, Broderbund and Spinnaker Software. Softkey became a billion-dollar company as a consolidator in the educational software market and eventually was moved from Toronto to Boston where it took the name of one of its acquisitions, The Learning Company (TLC). The Mattel company acquired The Learning company in 1999, in a $3.8 billion stock swap. O'Leary was born in Mount Royal, Quebec, a suburb of Montreal on July 9, 1954. His father was a salesman and his mother was a seamstress. He is of both Irish and Lebanese descent. Kevin became a co-investor and a director of the company Storage Now in 2003. They are a developer of climate controlled storage facilities. After a string of development projects and acquisitions, Storage Now has become Canada's third largest owner/operator of storage services. Storage Now had facilities located in eleven cities serving such major companies as Merck and Pfizer. The company was acquired for $110 million in March 2007. O'Leary is a wine enthusiast and he likes to play the guitar player in his personal time.