Kevin O’Leary was born in Montreal on 9 July 1954. His father died when he was young and his mother remarried an economist whose international work took the family abroad, which is why a man identified with North American business television spent part of his schooling elsewhere.

The story he tells most often about money is his mother’s: a retailer who quietly put a third of every pay cheque into dividend-paying stocks and bonds. It is the foundation of his public position on investing, and by his own account why he thinks about wealth as accumulation rather than an event.

He took a degree at the University of Waterloo and an MBA at the Ivey Business School, and after a short period in television production started SoftKey Software Products in the mid-1980s with a partner and a small amount of family capital. The company published consumer software: reference titles, educational discs, boxes sold next to the tills.

SoftKey was publicly traded by 1993, as The Globe and Mail records, and grew by acquisition rather than invention. The decisive move was a hostile bid for The Learning Company; the merged business took the TLC name, ran 3,000 employees and about $800 million of annual revenue, and lost money through 1996, 1997 and 1998.

In 1999 Mattel bought The Learning Company for roughly $4 billion in stock. It became one of the most criticised acquisitions of the era, and within six months O’Leary was out of a three-year contract as the losses mounted.

This is the event his wealth rests on, and the figure is documented. The Globe and Mail established that he netted $11.2 million from the deal, through his severance package and the sale of his Mattel stock — not the hundreds of millions the headline price invites people to assume. The $4 billion was the company’s price, paid mostly to institutional shareholders; the $11.2 million was his, and everything since started from it.

Television is where the second fortune came from. He joined the CBC’s Dragons’ Den in 2006 and ABC’s Shark Tank in 2009. On an episodic fee we put at around $50,000, rising towards six figures for a long-serving panellist, and roughly four hundred episodes across both shows, his gross television earnings come to about $25 million — our estimate, and far more than the 1999 sale paid him.

The platform then monetised itself twice over. A business speaker of his profile commands $50,000 to $100,000 an engagement, and he has published a series of bestselling personal finance books; together we carry speaking and publishing income at roughly $20 million gross across two decades. O’Leary Funds, launched in 2008, reached $1 billion under management within two years and was sold to Canoe Financial in 2015 with $800 million; he held 45 per cent of it.

He is known as Mr Wonderful, the panellist who tells founders their business is worthless and then offers a royalty deal. The character is a commercial asset in itself: it is why the speaking fees are what they are and why financial firms pay to put his name on a product.

In 2017 he entered the race to lead Canada’s Conservative Party and led several polls before withdrawing on 26 April, endorsing Maxime Bernier and saying he did not believe he could win in Quebec, as CBC reported. It lasted four months.

Endorsement income is a major part of his finances, and one episode of it is on the public record in unusual detail. He was paid to act as a spokesman for the cryptocurrency exchange FTX, and after its collapse he told a United States Senate committee in December 2022 that the fee had been $15 million, of which roughly $9.7 million went back into crypto and was lost, the rest to tax and agents, as CNBC reported.

That single arrangement shows the scale of what his name earns. Our estimate is that other brand and spokesman work has contributed a further $15 million to $25 million gross over the past fifteen years.

The venture portfolio is where most of the uncertainty about his wealth lives. O’Leary Ventures makes direct investments; O’Leary Fine Wines sells under his name; he has backed investing apps, bitcoin-mining capacity and dozens of companies from Shark Tank, where the sharks invest their own money rather than the network’s.

A portfolio of that shape is mostly illiquid. He has said he holds stakes in more than fifty private companies, and such a book is worth whatever a buyer pays: a few exits could be worth $80 million, or the same holdings could return a fraction of the capital. We carry it at $30 million to $80 million, the widest band in the arithmetic.

His property is spread across the places his work takes him: Toronto, Boston, Florida and a long-held family place in Ontario cottage country. Given his stated preference for income-producing assets over trophies, we carry $20 million to $30 million of real estate.

Alongside it sits the thing he is most credible about: a dividend-focused public-markets portfolio run on the principles he has sold in every book for twenty years. We put the liquid position at $50 million to $80 million, the largest single line in the estimate.