Just as his property website Zoopla was taking off, Alex Chesterman made a vow that there would be no more start-ups.
His wife had just said no to more children after their second — a decision he promised to match by calling it a day after two successful but time consuming businesses that yielded several hundred million pounds for the UK entrepreneur.
But that pledge was quickly broken. This week, the 51-year-old Londoner revealed plans to list his two-year-old start-up car retailer Cazoo in New York at a valuation of $7bn, using billionaire investor Daniel Och’s special purpose acquisition company.
The deal is his biggest yet — and the highest initial listing value of any UK company on the New York Stock Exchange. But it will be a major test for Chesterman as he seeks to scale up the business rapidly to justify a valuation that some in the UK tech market think rather high.
“Its certainly seems at the wrong value now,” said one prominent VC investor, “whether it will be in future is the question”.
But his record gives investors hope. For a…