Kevin O'Leary

Kevin O'Leary's father died when he was seven, and his mother, a self-taught investor, raised him and his brother in Montreal on the proceeds of stocks she picked herself, a lesson in market instinct he later credited more than anything he learned at business school. He is dyslexic, and earned a psychology and environmental studies degree at Waterloo before an MBA at Western's Ivey School. His first business, a sports-television production company, sold for twenty-five thousand dollars, money he put with ten thousand borrowed from his mother into a software startup called SoftKey in 1986, betting that home computers would need educational programs the way homes needed encyclopedias.

SoftKey grew by buying up struggling software companies, including The Learning Company for six hundred million dollars in 1995, then sold itself, as The Learning Company, to Mattel for 4.2 billion dollars in 1999, a deal Mattel's own board later called one of the worst acquisitions in corporate history, and O'Leary was fired within the year. He rebuilt on smaller, steadier ventures afterward: a data-storage company, mutual funds, exchange-traded funds, none as large as the Mattel windfall but real money nonetheless. Canadian television made him a personality on Dragons' Den starting in 2006, and American television made him Mr. Wonderful on Shark Tank starting in 2009, a persona built on blunt rejection that turned a mid-tier investor into one of the most recognized faces in business television.

O'Leary is not the billionaire his television persona implies, and he has said so himself, his real fortune traces to two deals, the Mattel sale and a storage-company exit, not to the investing record his shows advertise. He served as a paid spokesman for the cryptocurrency exchange FTX and lost roughly ten million dollars of his own money, along with whatever credibility came with the endorsement, when the company collapsed into fraud in 2022. Two years before that, on a lake in Ontario, a boat he and his wife were on collided with another vessel, killing two people; his wife was charged and later acquitted, while the confidence that made him a television star kept selling investment advice through both episodes.

O'Leary ran for the leadership of Canada's Conservative Party in 2017 and quit before the vote, unable to build support in Quebec, then endorsed the rival who inherited his voters. He has since become one of Donald Trump's louder business-world defenders, visiting Mar-a-Lago in 2025 and backing proposals to fold Canada into the United States, a position that startled the country he grew up in more than it convinced it. What survives from four decades in business is less a fortune than a brand: Mr. Wonderful, endlessly on television, still telling entrepreneurs exactly what is wrong with their pitch.

Kevin O'Leary's life against the full span of the corpus — the fading end marks a life still in progress.

• SoftKey International company
  Educational software company founded with $10,000, mostly borrowed from his mother 1986
• Sale of The Learning Company to Mattel company
  $4.2 billion deal later called one of the worst acquisitions in corporate history 1999
• O'Shares Investments company
  Exchange-traded fund company built around dividend-paying stocks 2015
• Shark Tank television
  Investor personality known as Mr. Wonderful 2009

• July 9, 1954 aged 0 Born in Montreal, Quebec
• 1980 aged ~26 Earns an MBA from the Ivey Business School
• 1986 aged ~32 Founds SoftKey with $10,000, most of it borrowed from his mother
• 1999 aged ~45 Sells The Learning Company to Mattel for $4.2 billion Fired within a year as the deal collapsed in value.
• 2006 aged ~52 Joins the cast of Dragons' Den in Canada
• 2009 aged ~55 Joins the cast of Shark Tank in the United States
• 2017 aged ~63 Runs for and drops out of the Conservative Party of Canada leadership race
• August 24, 2019 aged 65 His boat collides with another vessel on Lake Joseph, killing two people
• 2021 aged ~67 Becomes a paid spokesman for the cryptocurrency exchange FTX FTX collapsed into fraud the following year.

• Barbara Corcoran b. 1949
  Real estate entrepreneur who turned a $1,000 loan into a billion-dollar brokerage. Shark Tank co-star
• Daymond John b. 1969
  Founder of FUBU and Shark Tank investor who built a streetwear empire from a Queens home. Shark Tank co-star
• Donald Trump b. 1946
  Businessman, media personality, and 45th and 47th president whose populist movement transformed American politics. endorsed for president
• Warren Buffett b. 1930
  Value investor whose disciplined approach built one of the largest personal fortunes in American history. cites as an investing influence