1. Kevin O'Leary: Introduction
  2. Kevin O'Leary: Early Life and Education
  3. Kevin O'Leary: Success Story
  4. Kevin O'Leary: Net Worth
  5. Kevin O'Leary: Famous or Infamous
  6. Kevin O'Leary: Most Influential Quotes

While Kevin O’Leary was still at the University of Western Ontario’s Ivey Business School in 1979, he spent four months working at food manufacturer Nabisco, in downtown Toronto. While there, he worked as assistant brand manager for Nabisco’s cat food brands, and he had a hand in increasing the company's market share.

When he finished school, O'Leary asked two MBA classmates, Scott Mackenzie and Dave Toms, who had had assisted with the MBA documentary, to work with him on what he called Special Event Television (SET), a television production company. SET produced sports shows, as well as short in-between-period commercials for local professional hockey games. The partners later bought his stake for $25,000.

With that modest success under his belt, O’Leary began to cast about for his next business venture.

He believed he’d found the right opportunityin software. It was the 1980s, and software was not yet the multibillion-dollar industry it is today. But O’Leary saw the potential. He began to make the rounds, in scenes not too dissimilar from those on the television show Shark Tank, to ask investors for money. At one point, O’Leary seemed to have found just the investor he was looking for, one who was willing to commit $250,000 to the venture. But the backer dropped out at the eleventh hour. (See also: 5 Things Investors Can Learn from Shark Tank.)

The withdrawal devastated O’Leary, and forced him to be creative in launching his business. In 1986, at the age of 32, he took his proceeds from the SET sale, added another $10,000 his mother agreed to invest, and started his next company, SoftKey Software Products, Inc. Unable to afford office space, he started operations in his basement.

The company developed educational software for children and teens. Its software was user-friendly, designed for home-computer audiences and sold in "jewel-case" CD-ROMs.

After developing the software, SoftKey had to find a way of making money off of it. O'Leary’s first big success came when he enticed printer manufacturers to bundle SoftKey products with their hardware.

Before long, the company found that it couldn’t create new software fast enough to keep pace with demand, and it began licensing software from other companies to sell under the SoftKey brand. In the late 1980s and early ’90s, the burgeoning software market was mercurial, with new players and new technology emerging and vanishing seemingly every month. It was during this period that O’Leary became known for his blunt, aggressive style of doing business. (See also: 10 Characteristics of Successful Entrepreneurs.)

With steady revenues, SoftKey was able to buy the competitors it couldn’t outsell, taking on those competitors’ best products. In 1994, just eight years after its launch in O'Leary's Toronto basement, SoftKey was one of the main players in the educational software field, having purchased former competitors WordStar and Spinnaker Software. The next year, it bought The Learning Company (TLC) for $606 million. With the acquisition, O’Leary moved the company’s main offices to Boston, and adopted The Learning Company as the name for the entire company.

The acquisition was expensive and complicated, leading the newly consolidated TLC to two years of multimillion-dollar losses in 1996 and 1997. But the company emerged from the reorganization with a large chunk of market share in the educational software market, which earned it more than $800 million in 1998.  

Not content with the company’s place in the market, O’Leary continued to prowl for acquisitions. In mid-1998, TLC purchased another rival, software-maker Brøderbund, for $416 million.

By 1999, TLC was too big a player to ignore. And all of its acquisitions couldn’t have brought it to a prominent position in the software business at a more auspicious moment: the very height of the tech bubble. In late 1999, toymaker Mattel came knocking. This time, it would be TLC and its 467 software titles that would be acquired. Mattel paid roughly $4 billion in cash and stock for the company.

After thirteen years, O’Leary was experiencing the greatest success of his career. But he didn’t have much time to bask in it. As part of the deal with Mattel, O’Leary agreed to stay with the toymaker for three years. But after only six months, the company fired O'Leary. Although he received $5 million in severance pay, the fallout from the sale would go on for years.

Shortly after the deal with TLC, Mattel reported a $105 million dollar loss where it had projected $50 million in profits. The ensuing crash in its stock erased $3 billion of shareholder value in one day, inspiring commentators to call the deal one of the most disastrous transactions in corporate history. (For more, see: What lessons did the tech bubble crash give to investors in the Internet sector?)

As the losses piled up, shareholders sued top Mattel executives, along with O’Leary for lying about the viability of TLC during the acquisition process. TLC used dishonest accounting to hide losses and inflate revenues, the suit claimed. None of the allegations were proven in court, but Mattel nonetheless paid $122 million to settle the case in 2003.

With the Mattel-related legal matters behind him, O’Leary focused on looking for new investment opportunities. After a failed bid to buy video game maker Atari, he became a co-investor and director in Storage Now, which manufactures climate-controlled storage facilities for technology and pharmaceutical companies. In 2003, he paid $500,000 for 13% of the company. By 2007, he had sold his shares for more than $4.5 million.

In 2008, O’Leary co-founded O'Leary Funds, Inc. The mutual fund company’s offerings focus on yield and capital preservation.

With his fortune secure, O’Leary turned to writing. His first book, Cold Hard Truth: On Business, Money & Life was published in 2011, and his second, "The Cold Hard Truth On Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them," hit the shelves in 2012. The books, which focused on financial literacy, money management techniques and financial freedom were enough of a success to warrant a third, similar book in 2013. (For more, see: 6 Worst Financial Mistakes And Why You Made Them.)

O'Leary also took to the airwaves as co-host of a talk show on Canada’s national business television channel, then for a Discovery Channel show about climate change. Before long he was the co-star of CBC News Network's "The Lang and O'Leary Exchange." He also appeared as an investor on a Canadian show called "Dragons' Den."

O'Leary he is best known for his role as a potential investor on the hit American television show "Shark Tank," on which he has starred since 2009.

“There's something very visceral about watching people beg for money. It's powerful," he said of the show’s premise and its continued success.

Kevin O'Leary: Net Worth
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