Cazoo’s Alex Chesterman: “I’m not an innovator, just a copycat”

Serial entrepreneur Alex Chesterman likes to improve the consumer experience by spotting what’s broken, then fixing it. That’s been a successful strategy, but is he about to call it a day?

Cazoo's Alex Chesterman
(Image credit: © Cazoo)

Alex Chesterman has been described as “the most effective doer of deals in British business”. He’s certainly one of the speediest, says the Financial Times. Less than 18 months after launching Cazoo in December 2019, he’s planning to float the online used car-dealer for a hoped-for $7bn, using billionaire investor Daniel Och’s special purpose acquisition company (SPAC). It’s expected to be “the highest initial listing value of any UK company on the New York Stock Exchange”. Britain’s second-hand car market is notorious for its sharp-elbowed dealers – as encapsulated in the 1980s TV series Minder. But a deal that size is enough to have Arthur Daley spinning in his grave.

Chesterman, 51, who talks of building “the Amazon of cars”, doesn’t lack confidence or backers – Cazoo’s existing investors include BlackRock, Daily Mail owner DMGT and Octopus. Yet competitors have begun to ask how a fledgling venture, which lost £88m last year on sales of £162m, can reasonably command such an astonishing price tag, says The Sunday Times. By contrast, “unloved” rival Lookers is worth just £213m. A good deal of the answer lies in Chesterman’s pedigree as a disruptor.

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Jane writes profiles for MoneyWeek and is city editor of The Week. A former British Society of Magazine Editors editor of the year, she cut her teeth in journalism editing The Daily Telegraph’s Letters page and writing gossip for the London Evening Standard – while contributing to a kaleidoscopic range of business magazines including Personnel Today, Edge, Microscope, Computing, PC Business World, and Business & Finance.

She has edited corporate publications for accountants BDO, business psychologists YSC Consulting, and the law firm Stephenson Harwood – also enjoying a stint as a researcher for the due diligence department of a global risk advisory firm.

Her sole book to date, Stay or Go? (2016), rehearsed the arguments on both sides of the EU referendum.

She lives in north London, has a degree in modern history from Trinity College, Oxford, and is currently learning to play the drums.