Alex Chesterman had already sold two companies when he started selling cars online. Neither of them had anything to do with cars.
He went to St Paul's School in London and then studied economics at University College London. He was born on 9 January 1970. His first big job was at Planet Hollywood, where he became an executive vice president and stayed until 1998. That was the moment he decided to start something of his own.
What almost nobody expected was where he would go with that money and name.
That something was ScreenSelect, a DVD-by-post service that became LoveFilm. Amazon bought it for GBP 200m. He was not finished. In 2007 he founded Zoopla, a property website, floated it in 2014 at a valuation close to GBP 1bn, and sold it to Silver Lake in 2018 for GBP 2.2bn.
What almost nobody expected was where he would go with that money and name. He picked used cars, a market of shaky trust and heavy cost. In December 2018 Cazoo announced a round of more than GBP 30m, then raised another GBP 50m before launch. By 2020 it had raised GBP 180m in total.
The pitch was simple: buy the car yourself, check it, deliver it. But owning stock turns a website into a car dealer. A marketplace carries other people's risk. Cazoo carried its own.
Chesterman stepped aside as chief executive in January 2023, and left the company that December. In May 2024 Cazoo entered administration.
His own wealth had been put at GBP 750m in the 2021 Sunday Times Rich List. He was also a visible political figure, giving GBP 300,000 to the Liberal Democrats for the 2019 election.
For a founder the lesson is about capital intensity. Two asset-light digital businesses made him rich. The third needed warehouses, reconditioning and vast inventory, and it asked a different skill. A founder's track record transfers, but it does not guarantee the economics.