Bill Gates, who knows a bit about winning, said, “Success is a lousy teacher. It seduces smart people into thinking they can’t lose.” The once-successful Australian realtor Harry Kakavas probably agrees — now.

Beginning in June 2005, he lost over $1.5 billion in 14 months playing baccarat in a Melbourne casino. When it comes to losing spectacularly, he’s up there with the 1930s Coca-Cola CEO who repeatedly decided not to buy Pepsi Cola. According to HistoryCollection.com , “Pepsi went on to eclipse Coke in sales in the 1980s, and in 2005 PepsiCo surpassed the Coca-Cola Company in market value.”

Then there’s Dick Rowe, the head of Britain’s Decca Records who signed megastars like the Rolling Stones, the Animals, Tom Jones, and Van Morrison, and one of the great losers of my generation.

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