Rupert Murdoch has built his empire by gambling with the family ranch time and time again.
His News Corporation conglomerate nearly went belly up when he overstretched himself in 1990, borrowing from more than 140 banks to fund the launch of Sky in the UK and Fox in America.
However, there is no doubt his successes far outweigh the failures.
Mr Murdoch has singlehandedly built a media group with strong positions in content and distribution, while maintaining family control of the firm throughout.
It is hardly a rags to riches story - Mr Murdoch's father was a famous newspaper tycoon - but he is undoubtedly a modern day William Randolph Hearst.
But the failure of the multibillion-pound DirecTV takeover this year was Mr Murdoch's biggest disappointment and time is running out for him to seal another one of his trademark deals.
The deals that made the difference
1952: Inherits the Adelaide News from his father, Sir Keith Murdoch.
1953: Takes over News Ltd in Australia.
1964: Launches the Australian, his first national newspaper.
1969: Takes over the News of the World and The Sun in the UK. Larry Lamb, the founding editor, invents modern tabloid journalism.
1973: Buys San Antonio Express News in the US.
1976: Buys the New York Post from Dorothy Schiff. Also buys The Village Voice and New York Magazine.
1980: Establishes News Corporation.
1981: Takes over the Times and Sunday Times in the UK with a controversial deal that wriggles through a monopolies commission loophole.
1983: Launches the first ever satellite TV channel, Sky. Sky uses a European telecommuncations satellite, Eutelsat, owned by European state post and telecoms operations, including BT.
1985: Takes control of 20th Century Fox in the US. Acquires Metromedia's independent television stations from John Kluge for £1.5bn, giving him a presence in six major US cities. Sells the Village Voice.
1987: Buys South China Morning Post. In the UK, buys Today newspaper from Lonhro for £38m and takes 15% stake in Pearson, which he later sells.
1988: Forced to sell the New York Post to the real estate developer, Peter Kalikow, when media ownership rules are tightened. Pays Walter Annenberg £2bn for Triangle Publications, owner of TV Guide. He announces plans for the Sky satellite channel across Europe.
1989: Increases investment in Sky TV dramatically as a new commercial satellite, Astra, is planned by Luxembourg government. Announces plans for five channels: Sky Channel, Sky News, Sky Movies and Eurosport and Sky Arts.
1990: British Satellite Broadcasting merges with Sky to form British Sky Broadcasting.
1992: BSkyB buys the broadcasting rights to the Premier League for £300m in a joint bid with the BBC. Four years later, it pays £670m to renew the contract and last year it paid £1.1bn.
1993: Buys back the New York Post after a financial crisis plunges the publication into turmoil. News Corp pays £325m to take control of Hong Kong-based Star TV.
1997: Buys the Los Angeles Dodgers baseball team for £240m.
1998: Floats 18% of Fox Entertainment Group.
2000: Buys Chris Craft Industries and United Television in the US (10 TV stations in total) for £3.6bn.