WHEN Grahame Whateley failed his O-levels, he was stripped of the captaincy of the school rugby team and the headmaster gave him four strokes of the cane.

The punishment clearly had some effect. Not only did Whateley resit the exams and pass them, but he has failed at few things since and now runs Britain’s biggest private property developer.

Castlemore Securities, of which he is chairman, is developing retail, office and leisure properties worth more than £1 billion. Last year the company had sales of £146m and profits of £17.8m.

According to The Sunday Times Rich List, Whateley is worth £165m and has homes in Worcestershire, France and Majorca.

Born and brought up in the Birmingham suburb of Moseley, Whateley, was an only child. He was just seven years old when his father died.

After leaving school he joined John Howell and Co, a small firm of surveyors.

“I was very lucky,” he said. “I was tremendously ambitious and John Howell was a great character. He made a tremendous impression on me.”

Work, however, was hard. “On Mondays and Tuesdays I would collect the rents for our clients. These were the days of back-to-back housing and rents were less than £1 a week.

“For three years, in summer and winter, rain and shine, I would traipse round Birmingham and the Black Country collecting rent.”

On Wednesdays he was allowed to go to auction sales to watch his boss buy properties. “I could see a tremendous opportunity to make money,” said Whateley. “In those days you could buy a dozen properties for £20,000.

“All of them would have protected tenants except perhaps one, which would be vacant. You could do it up and sell it for £6,000 or £7,000.”

After four years he left to start a small agency selling commercial property. One of his first clients was Tony Dillon, who bought a newsagent’s shop from him. Over the next 18 months Whateley found him a lot of newsagent’s shops to buy.

By the time he was in his early twenties, however, Whateley realised that as an agent he would only ever earn commissions. So he persuaded a bank to lend him the money to buy a chain of newsagents. In 1967 he sold them to Dillon, who went on to create the Dillons convenience store chain.