Currently the chief executive of used car marketplace Cazoo, he previously founded property site Zoopla, and cofounded film rental site LoveFilm — which formed the basis for Amazon Prime.
Chesterman is one of the UK's most prominent entrepreneurs, behind successes including film streaming site LoveFilm; property aggregator Zoopla; and latterly car marketplace Zoopla. "We wouldn't have built the business we did if it wasn't for the financial crisis," Chesterman continues. "Everyone else was running to the exit which meant we could run to acquisitions."His current project, Cazoo, is a used car marketplace which recently surpassed a valuation of $1 billion. Between his various startups, Chesterman has raised more than $560 million in venture and equity funding.
"When you're investing at the early stage you're making a judgement on a person," Alliott Cole, CEO of Octopus Ventures and a backer of all three of Chesterman's businesses, told Business Insider in an interview. "He has the confidence and intention to succeed paired with a certain charisma alongside a common sense view of the world."For Chesterman, Covid-19 presented an even greater challenge than 2008.
"When you have a known quantity it's better but the margins between success and failure can be very thin, especially if the market goes against you," Cole adds. "Alex has found a way to navigate that and come out of it stronger and that's what you're investing in.Chesterman and several of his investors also happen to fit an uncomfortable wider pattern — that the best-funded British entrepreneurs still tend to be white and male.
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