2 for 1 tickets to Singin' In The Rain, this coming Monday. Book now
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.
Enjoy screenings of all the classic films you love, plus take advantage of two-for-one tickets
Have you ever dreamed of owning your own racehorse or a beautiful painting?
Enjoy comfort, safety, space and great design. Plus enter our great competition
Times Online's new TV show helps you make the right decisions for your pet
Are you California dreaming? Explore the wonders of the Golden State. Also enter our fantastic competition
Do you have what it takes to be a Times photographer?
Your brain is capable of more than you might think...
Find out to make the most of your money with our wealth management guides
Need help with your property? We have an entire how to guide - buying, selling, letting, moving, to help you
We are seeking entries for the inaugural Sunday Times Best Green Companies Awards
Enjoy some wonderful inspiring wildlife moments
An interactive preview of the brand new For Your Eyes Only exhibition

Love Sudoku? Play our brand new interactive game: with added functionality and daily prizes

Are you irritable when you return from work? Drained of emotion? You could be suffering from boreout
Prepare for some shock and awe, petrol lovers. Despite the greens trying to wipe it out, the car is about to offer us the most exciting year ever
We've trawled the brochures and websites to find this summer’s best holidays for every taste and budget


Income, Life Insurance, Critical Illness Cover
2007/07
£57,500
South East England
2007/07
£40,995
South East England
2006/06
£41,995
South East England
Great car insurance deals online
£40-55k+benefits+uncapped commission
Morgan Keating
South East
Up to £30,000
GLE
London
£
c£75,000 + executive benefits
Morgan Keating
London and South
Unpaid with travel expenses
Network Rail
Globrix, the property search engine
Visit Times Online Property for homes for sale or rent
Residential development site with planning permission
£1,500,000
Mortgages, bank accounts & money transfers to help you buy abroad
Dinarobin Hotel Golf & Spa 7 nights
From £1830 per person – saving £530.
Walking & multi-activity holidays in Cauterets. Stylish self-catering apartments.
From 350€ for 7 nights.
SAVE 25% on Sandals Luxury Resorts
Great travel insurance deals online
Contact our advertising team for advertising and sponsorship in Times Online, The Times and The Sunday Times. Search globrix.com to buy or rent UK property.
© Copyright 2008 Times Newspapers Ltd.
This service is provided on Times Newspapers' standard Terms and Conditions. Please read our Privacy Policy.To inquire about a licence to reproduce material from Times Online, The Times or The Sunday Times, click here.This website is published by a member of the News International Group. News International Limited, 1 Virginia St, London E98 1XY, is the holding company for the News International group and is registered in England No 81701. VAT number GB 243 8054 69.