What Cars Do The Top Entrepreneurs Own & Drive? We Find Out


So you’ve made your millions, or in a few cases, billions. One of the main concerns when buying a new car is money, but to a successful entrepreneur money is of no object. Some maybe frivolous and go all out on the latest fire-spitting Lamborghini, or the more tame entrepreneur of whom profit and limiting expenditure is of the upmost importance may opt for something robust, economical, eco-friendly or even diesel.

So out of the kingpins of business, who drives what?


Richard Branson


We’ll start with this businessman and investor. I grew up in the 90’s and Virgin was everywhere: Virgin Mobile, Virgin Radio, Virgin Atlantic and more recently Virgin Trains and Virgin Active gyms. From starting up a tiny record store called Virgin, this man now owns his own island, two private jets and spends his past time messing about with hot air balloons and jet packs and travelling into the atmosphere. He has literally reached dizzying new heights and depths – from deep-sea exploration in his own submarine to space travel with his pioneering Virgin Galactic Company, this great business mind isn’t one to sit behind a desk in an office!

Although Branson may get chauffeured around in the usual S-Class or Rolls-Royce when travelling, these are three of his personal cars:


James Caan


Initially working for his father’s leather jacket firm, at 18 years old, James Caan moved into the recruitment sector. Just six years on and he founded his own company, eventually selling his stake for £25million. Caan has since set up Hamilton Bradshaw, and for a few years he was an investor on BBC’s Dragons’ Den.

Caan has owned more than 25 cars. Numerous Porsches, the 911 Turbo and the 928 S4 as well as four Rolls-Royce Corniches, five Spirits and various Bentleys plus a Maybach 62.


Bill Gates

How could we leave Bill Gates out? Virtually every living soul on earth has contributed to his fortune by using his Microsoft software and that little known operating system called Windows. I’d go as far as saying Gates is one of the most influential men of the past century, giving billions of dollars to charity.

Aside from all that geeky stuff, Gates is fascinated with vehicles. Although he has enough money to build a city on the Moon, Gates has been seen behind the wheel of a Ford Focus. Like Caan, Gates loves Porsche, his collection including the 911 Carrera, the 930 (bought in Microsoft’s early days) and one of the most famous supercars, the Ferrari F40-challenging 959.


Simon Cowell

Straight-talking media mogul Simon Cowell is a massive petrol head. At 17 he got a job in the post room at EMI Music Publishing and since then music and entertainment have been changed dramatically thanks to his X Factor and …Got Talent franchises. His net worth of £300million means he is often seen in various different exotic cars. Here’s a small taste of his most striking.


Alan Sugar

Business heavyweight Alan Sugar opted out of education aged 16 and began selling electrical items from the back of a van. Five years on and he registered the name Amstrad. The company title was devised taking letters from his own name: Alan Michael Sugar [trad]ing. Sugar is best known today from the TV series the Apprentice, where young upstarts compete tasks to win landing a job working for the cockney Tycoon.

Part of Sugar’s car collection includes a Range Rover, a Rolls Royce Ghost which wears the famous ‘AMS 1’ number plate, a Classic Rolls Royce and a Bentley Continental GT – pretty standard in the world of jet set business travel. The car pictured below however, the one of the far left, is a Bentley S1 Continental Two Door Fastback Coupé by H.J. Mulliner previously owned by Sir Elton John.


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