One of the top "rainmaker" bankers at Goldman Sachs is set to make big personal profits from the mooted $8 billion dollar stock market flotation of online car dealer Cazoo, which Goldman is advising on.
Anthony Gutman invested in early stage fundraising rounds last year.
Some London fund managers expressed concerns of a conflict of interest in Goldman's selection as one of the key banks advising on the float.
Goldman and Gutman declined to comment but sources at the bank said he was not involved with its selection as an IPO adviser. All Goldman Sachs partners' private investments have to be vetted and approved by the company.
Subsequent rounds of financing make it impossible for outsiders to gauge how much Gutman's stake may now be worth, but he was one of notably few named individual investors in the early fundraisers.
Filings for Cazoo Limited from 2020 show he owned 75,000 series A shares and 29,412 series B shares.
That was dwarfed by founder Alex Chesterman's 2 million series A shares and 60 million Ordinary shares at the time, but could be worth a small fortune if the IPO valuation proves as huge as the company hopes.
A bigger outside early stage investor, whose stake is set to be worth billions on the float is the newspaper group Daily Mail and General Trust which recently said in a stock market announcement that it owns 20% of the company.
Last year's filings showed it had 15 million and 7.3 million A and B series shares respectively.
DMGT made the investment through its Ventures investment arm.
Octopus, the investment group, is another keen early stage backer.
Gutman is known to be an enthusiastic early stage tech investor and a big believer in the prospects for European technology companies.
Generally low profile, Gutman hit the headlines in 2016 when he was hauled in front of a government select committee to be questioned about Goldman's involvement in Sir Philip Green's sale of BHS to former racing driver Dominic Chappell before its collapse.
Cazoo would not comment on his involvement in the business.
Cazoo is yet to decide whether to follow Deliveroo with a London Stock Exchange listing or opt to merge with a US-listed special purpose acquisition company (Spac).
Spacs are shell companies which raise funds to buy businesses.
Some London fund managers say Cazoo would struggle to attract London Stock Exchange investors at such a high valuation, given that the company was only founded two years ago and only went live in December 2019.
The group has already privately raised £450 million - more than two times the entire stock market value of car dealing giant Pendragon and over three times that of Vertu Motors.
It bought car supermarket group Imperial Cars last July, giving it 18 used car sites to trade from. It says it has sold 20,000 cars so far and made over £200 million in revenues since launching.
Some in the motor trade have questioned its business model given that conventional car dealers make very little margin on selling used cars.
Cazoo fans, however, say it will be able to use its financial muscle to ape Amazon and sell so many cars that the small margin will eventually add up to big profits.
They also point to the rapidly growing market share in the US of Carvana, which has a similar business model. Carvana floated with a value of $2.1 billion in 2017 and is now worth $46 billion.
Critics also say people will not buy a car online without test driving it and checking it out physically first. Chesterman told the Evening Standard last year: "Fifteen years ago, people said there's no way anyone will buy clothes online."
Heavy advertising firepower and a growing infrastructure of Amazon-style car warehouses will represent a "moat" around the business that will make it hard for conventional firms to compete with, Cazoo's supporters say.
Founder Chesterman has had previous entrepreneurial success building up LoveFilm and selling it to Amazon for £200 million then creating property website Zoopla before floating it in 2014.
It was sold four years later to private equity group Silver Lake for £2.2 billion.