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But Wood, who set up Direct Line in 1985, left in 1997 and has launched six more firms before and since, did not make millions out of insurance without knowing how to hedge those bets.
Hence he always shares the risk with partners. And despite being a supremely self-confident entrepreneur with a gift for organisation and numbers, he also knows when to rein himself back.
So last week he announced he was walking away from the two firms he started up in America, freeing up more time for Esure, the internet car-insurance venture he launched with HBOS in 2001.
Esure, which he chairs, should come into profit later this year, and already has a sister firm, First Alternative (targeting drivers who find insurance hard to get). It opened for business eight days ago.
Wood, 58, a legend in the insurance industry with a personal wealth estimated at £100m, also has a dream house being built here, a restaurant he co-owns round the corner from Esure’s offices, plans for a hotel he wants to open, two ex-wives, five daughters and the odd girlfriend to keep up with — yup, enough to focus on in the UK now without distractions.
So have his American insurance ventures (Response, set up in 1995, and Homesite in 1997) failed? Wood, elbows on the table in his third-floor office in Reigate, Surrey, seems for once lost for words. “Failure?” he asks eventually. “Um, no, no.”
It’s simply that the time involved in keeping an eye on the American ventures meant he couldn’t stay on top of Esure. “I just thought this was ridiculous, Esure is growing and it’s been tough in the US.”
So he is “retiring” from his interests there in what he describes as a “complicated transaction” with his partners, no details given.
Has he lost money? He doesn’t quite answer that. “I didn’t make loads of money, but the shareholders are OK. I just don’t want to spend the next three years doing trips across all the time.”
His house in Boston, just across Louisburg Square from John Kerry’s, will shortly go up for sale. Instead, he will spend more time in Surrey and Spain, where he has a vast holiday villa in Marbella, and concentrating on the fun things with which he keeps himself busy.
“I have taken control of underwriting, finance and claims at Esure,” says Wood, “so the chief executive has more time to spend on marketing and IT.” He gives a little grin. Wood, you’d guess, is only happy when fully immersed.
And it doesn’t seem to be doing him any harm. Lithe and tanned, with cautious eyes and a jibe never far from his lips, he looks like Des O’Connor’s smarter, younger brother. Everything about him is spotless: the room, the clothes, not a hair out of place. Like many highly numerate minds, his has an obsession with order.
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