With the launch of his real estate website Zoopla, Alex Chesterman swore that there would be no more startups.
His wife refused to more children after the second. He promised a British entrepreneur that he would match by calling two successful but time-consuming businesses in one day, which made hundreds of millions of pounds.
But that promise was quickly broken. This week, 51-year-old Londoner announced plans to list two-year-old new car retailer Cazoo in New York for $7 billion using a special-purpose takeover company from billionaire investor Daniel Och.
This deal is his biggest deal and the highest initial listing value of any UK company on the New York Stock Exchange. However, Chesterman’s efforts to quickly expand his business to justify the valuations that some of the UK technology markets consider rather high will be an important test.
One prominent VC investor said, “It certainly seems to be the wrong value now,” he said. “It’s a question of whether it will be in the future or not.”
However, his record gives investors hope. An imitator who confessed to himself the ideas of others, Chesterman turned his frustrations about a market in need of change with several fortunes and had a lasting impact on British consumers.
Lovefilm, a DVD rental service that sold to Amazon for £200 million in 2011 in response to Netflix in the UK, started before the end of the high street video store.
Zoopla, a real estate portal where he left in 2014 and earned about £300 million by selling it to Silver Lake for £2.2 billion in 2018, fell into a British obsession with the value of others’ homes in return for traditional real estate brokers .
He wants Cazoo to do the same on the used car sales site. In other words, it makes the vehicle buying process faster, cheaper, and delivers purchased items to your home.
If you think like a consumer and think there is a way to improve that market, most consumers will think the same.
Chesterman, who owns a quarter of Cazoo in this deal, will earn a similar sum from the company’s last private fundraiser last fall.
All three startups came from discovering the success of another company in the United States (Cazoo in a TV commercial for American car dealer Carvana), but they were ported and altered for the European market.
He called it “second mover advantage. . . We’re new to our market, but let others figure out what works and what doesn’t.”
Chesterman is often treated with suspicion by the incumbent. Some dealers are still skeptical about whether Cazoo will make a profit. He may not know more about these markets, but he admitted that ignorance could be an advantage.
“To fix a broken object,” he says. “I love watching movies, I live at home and drive my car. If you think like a consumer and think there is a way to improve that market, most consumers will think the same.”
Educated at St Paul’s School and University College London, Chesterman got an offer to work for Goldman Sachs when a family friend offered him to assign him to a management program at Hard Rock Cafe in Florida.
He tried to spend a three month sabbatical there, but spent 10 years in the United States, initially running a Hard Rock branch, and the same friend started Planet Hollywood, joining as one of the first employees.
Returning to London in a family emergency, in 1999 he tried to continue the hospitality business in the bagel shop chain. Realizing that it was more valuable than real estate, he found an opportunity in the mid-Newti tech field on DVD. Delivery.
Those who work with him say that he can be emotionally separated and obsessed with details. Others describe him as a great deal maker, knowing the best time to combine him with his small rivals to build and sell a business.
One person who worked closely with him said, “He’s not a flash man. He works all the time. He was able to retire years ago.”
Chesterman drives the Range Rover. -Although Cazoo said he would buy the next car in due time-he lives in a house in Highgate, London. His money is spent on vacation with his family, but as an angel investor he also bought shares in startups such as Graze, CarWow, and Farmdrop.
But now his time is dominated by Cazoo, and I think he’s the biggest opportunity to date. It predicted that it would be a £20 billion business. While he’s floating in New York, he says he wants to take his business to the investors who understand it best, and that London doesn’t want to grow fast, he doesn’t want to lose startups. The listing reform promised by the government would not have changed it.
“I think this is probably my last thing,” he said of his relationship with Cazoo before adding: “But I’ve said it before.”
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