When Jonathan “Jonty” Pain was growing up in apartheid South Africa, he shocked his father by leaving the nation’s most prestigious all-white male boarding school, Hilton.

Pain wanted to go to the multi-ethnic school, Waterford in Swaziland. But the school was dismissed by his father as a hangout for “drug addicts and hippies”.

Against his father’s wishes, Pain made one of his first great decisions.

For Pain a multi-ethnic environment was where he was happiest: at Clifton Preparatory school he sometimes ate with the black kitchen staff.

Raised by black nannies in Lesotho after his mother died before he was 10 years of age, Pain remembers trying to take an elderly black man into a store in Bloemfontein over the furious objections of a young Afrikaner, who accused him of being a “kaffir lover”.

At Waterford Pain went to school with Zinzi Mandela and Naomi and Mpho Tutu, children of future Nobel Prize winners.

“I felt totally liberated at Waterford and completely at home,” says Pain. Naomi Tutu, who he hasn’t spoken to since 1979, recently wrote to him asking him to help her daughter when she comes to Sydney to study at the University of New South Wales.

Pain’s boyhood interest in current affairs was nurtured at Waterford and when he left for England to study at Keele University, he decided to study economics and politics. Later he would do a master’s degree in finance at the University of Exeter.

He would not return to live in South Africa. After marrying his English-born university sweetheart, in 1984 Pain joined a growing crowd of graduates who sought their fortune in the City of London.

Pain’s wife, who edited his writings and provided counsel, died on Valentine’s Day 2010. Pain still wears his gold wedding band. “I can’t take it off,” he says.

In London Pain worked as a portfolio manager at US bank Manufacturers Hanover. He then went to Bahrain in 1986 to work for Gulf International Bank, where he helped manage a global investment portfolio.

In 1990 Paribas brought Pain back to London to head global asset allocation. He remembers some being dismissive of his relative youth and inability to speak French.

In 1992 the Middle East called again. Pain was hired to be the head of investments at Gulf. His wife loved the Middle East and Pain developed a life-long affinity with the region. He often turns discussions on global politics to the Middle East, happy to talk about the volatile cocktail of oil, religion, super powers and royalty.

In 1997 Rothschild Australia Asset Management hired Pain as their chief investment officer. In 2002 he became a consultant for Hedge Funds Australia where he began to write the Pain Report for the company’s clients. He claims credit for tracking and predicting the pricking of the credit and internet bubbles.

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