Alex Chesterman led Zoopla’s parent company to a £2.2 billion sale, stepped back, and turned to his other investments. Then he started a company that owned the cars it sold. This is the story of what pulled him back.
In September 2018, Alex Chesterman did what most founders only talk about, so the story goes, two months after Silver Lake bought ZPG, the group behind Zoopla, for £2.2 billion, he said that, “now is the right time for me to step down as CEO."
He kept his seat on the board and turned to his other investments.
Now, Lovefilm had already gone to Amazon in a deal reported at £200 million, with £20 million of that his, and he had spent years backing other founders on the side.
A second exit, a second fortune, and a long run of angel investing would have been a perfectly good ending to the story.
But instead, in May 2021, the Sunday Times Rich List welcomed him as a new entry at £750 million, 215th in the country, and the paper openly asked whether he might become a billionaire.
The business behind that very question sold used cars online and was called Cazoo.
So what makes a man who has already won twice walk back into the arena?
Two Wins and a Method
Chesterman’s record up to that point looked like a method, and he set out to build Zoopla in 2007, funded by his Lovefilm earnings, aiming to become the number two in a property portal market dominated by Rightmove.
Zoopla never really overtook Rightmove, but over a decade it grew into a group with annual revenues above £300 million.
He has also been unusually open about where his ideas come from.
“…seeing a model in the US that was really solving a problem”—Alex Chesterman, on how he chose Lovefilm, Zoopla and Cazoo, quoted by SmallBusiness.co.uk, 2021
Zoopla, though, held nothing, and it showed customers other people’s homes, and we think that detail matters for everything that came next, because Cazoo sat at the opposite end of the spectrum.
A Company That Owned the Cars
Cazoo launched in December 2019 as an online used car retailer, and the difference from Zoopla was built into its structure.
Cazoo bought cars, held them as vehicle inventory, and delivered them in its own uniformed vehicles.
Chesterman had heard the doubters before, when he entered film rental, he recalled people asking, "What do you know about the film industry?" and then he heard the same about property in 2007 and then again about cars.
Cazoo reached unicorn status faster than any UK firm before it, and football sponsorship followed, with Aston Villa and Everton among the clubs carrying its name.
Was this the Zoopla playbook carried into a new industry or a totally different game altogether?
Chesterman had planned to slow down, and the Sunday Times reported that the chance to transform the used car market was too enticing to resist.
When he announced the funding in December 2018, his promise was plain.
“no different to buying any other product online today”— Alex Chesterman, on Cazoo’s aim, December 2018
A Listing Worth Billions
In August 2021, Cazoo completed its NYSE listing through a SPAC merger, at a valuation reported at between $7 billion and $8 billion, depending on the source.
The Rich List reported that Chesterman had actually sold £100 million of his own shares before the company appointed bankers to work on the float.
Cazoo’s administrators would later put its 2021 loss at £329 million, up from £103 million, and say the share price fell by about half in the first year and about 99 per cent within two.
So how does a company valued in the billions lose almost everything in under two whole years?
In May 2022 Chesterman told The Times that the slump reflected irrational fear in the stock market.
Days later, Cazoo’s own annual report, filed late with the SEC, carried a warning in the standard language of such filings.
“may never achieve or maintain profitability” — Cazoo, in its annual report filed with the SEC, May 2022
What Happened to Cazoo?
By January 2023, Chesterman had stepped down as the chief executive.
That December, a $630 million debt-for-equity swap made Viking Global, the US hedge fund, Cazoo’s biggest shareholder.
Then, in 2024, came the big plot twist we think deserves more attention than it has received: Cazoo announced it would stop being a retailer and become a third-party marketplace, selling off all of its vehicle stock along the way.
The sale repaid its stocking loans in full and left a surplus of £30 million, and it removed the very thing that had set Cazoo apart from Zoopla, so a company built to be unlike Zoopla spent its last months turning into it.
Less than six months after the debt-for-equity swap, on 8 May, the directors filed notice of their intention to appoint administrators, and about 700 jobs had already gone in the first quarter, and with Cazoo in administration by 21 May, more than 10,000 unsecured creditors came forward with claims totalling £259 million.
The name and marketplace were sold to Motors, reportedly for £5 million, and in May 2026 the High Court extended the administration until May 2028.
So what happened to Cazoo?
The administrators gave their own answer as a list of factors, and these two came first.
“aggressive expansion strategies, a competitive market”— Teneo, Cazoo’s administrators, in their proposals to creditors, August 2024
The Question Cazoo Leaves Behind
Industry opinion has not settled on a single cause.
A survey of 62 used car dealers found half blamed the limited potential of online-only retail, and more than a third believed investors had overestimated what technology could do.
One trade voice argued that buying its own stock was the fundamental mistake. The ending has its own irony: Zoopla has since appointed a former senior Cazoo executive as its chief executive.
Alex Chesterman, for his part, dropped off the Rich List in 2023 as Cazoo’s value slumped.
He had been one of UK's most prolific angel investors before Cazoo, backing Carwow, Secret Escapes, and Graze.
Did Cazoo fail because the model was wrong, or the timing was wrong, or the scale arrived before the economics did? And does the story of Alex Chesterman, a founder who made his name finding room beside market leaders, read differently when the room turns out to need warehouses and delivery fleets?
We do not know, and the answers lie with the people who ran it.
Which leaves the question we would most like to put to Chesterman: what comes next, and will his next business own the assets behind its growth, or simply connect the people who do?
What We’d Still Like To Ask
We can set out what happened to Cazoo, but the reasoning behind each decision is still Chesterman’s to give.
Zoopla had shown that a marketplace could work without owning anything, so what made holding vehicle inventory look like the right next step?
He had heard from doubters in film, property, and cars that he did not know the industry, so at what point, if any, did Cazoo show they had a point? And having watched Cazoo in administration, what has he taken from it about how he backs founders now?
Those are the questions we would most like to put to him.
Editorial note
This piece is purely based on secondary research.
We have not spoken to Alex Chesterman or his team, or anyone who worked with him at Lovefilm, Zoopla, or Cazoo, but we would welcome the chance to hear his account of Cazoo.
We also welcome any additional context, corrections, or first-hand perspectives from anyone with relevant knowledge of the story.
Also Read: What Is a Knowledge Intensive Company? EIS Status, Criteria and Limits Explained
Sources: Car Dealer Magazine (Rich List, May 2021; Times interview and SEC filing coverage, May 2022; Cazoo failure podcast, September 2024; administrators’ reports; High Court extension, May 2026); City AM (Cazoo launch funding, December 2018; administrators’ proposals); SmallBusiness.co.uk (Chesterman profile, 2021); Mishcon de Reya (Jazz Shapers interview, 2019); Property Industry Eye, The Negotiator and Estate Agent Today (ZPG step-down, September 2018); Auto Retail Network (Teneo report, August 2024; Rich List 2023); Carwow (Cazoo administration explainer, May 2024); Startline Motor Finance (dealer survey); Dealroom and Financier Worldwide (Cazoo timeline).
